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Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

3 Beds ⋅ 3 Baths ⋅ TB8556740 MLS

Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

102 Windward Drive, Osprey/Nokomis

$639,000

This exquisite three-bedroom, three-bathroom, PLUS office/den residence by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. This rarely available, waterfront, Savannah model features a sizable great room and intricate tray ceilings, showcasing clean lines, crown molding, and plantation shutters. The gourmet kitchen is a chef's dream with natural gas range, solid wood cabinetry, granite countertops with a coordinating backsplash, and stainless-steel appliances. The breakfast bar and casual dinette offer picturesque water views through a large aquarium window. The desirable split plan affords privacy for family and guests, with an expansive primary bedroom providing a spacious sitting area opening to the lanai, dual walk-in closets, and en-suite bath complete with dual sinks, garden tub, walk-in shower, and water closet. Sliding glass doors lead from the great room to the screen enclosed, covered lanai, with ample space to grill, entertain, and dine. Experience peace of mind as this home has motorized storm shutters, and a 22 KW Generac generator that comes with a transferable warranty until 2028. HVAC 2020 with a 10-year warranty and whole house water softener with reverse osmosis. Low HOA fees include high speed internet, Direct TV streaming, yard maintenance, irrigation, and access to the community amenities inclusive of the heated pool and spa, fitness center, pickleball, basketball, and playground. Conveniently near beautiful Gulf beaches, Oscar Scherer State Park, Legacy Bicycle Trail, Pine View School, a variety of waterfront restaurants, and shopping.

3 Beds ⋅ 3 Baths ⋅ A4702490 MLS ⋅ Lee Wetherington BLDG.

This exquisite three-bedroom, three-bathroom, PLUS office/den residence by Lee Wetherington Homes exemplifies intelligent design and beauty in the community of Willowbend. This rarely available, waterfront, Savannah model features a sizable great room and intricate tray ceilings, showcasing clean lines, crown molding, and plantation shutters. The gourmet kitchen is a chef's dream with natural gas range, solid wood cabinetry, granite countertops with a coordinating backsplash, and stainless-steel appliances. The breakfast bar and casual dinette offer picturesque water views through a large aquarium window. The desirable split plan affords privacy for family and guests, with an expansive primary bedroom providing a spacious sitting area opening to the lanai, dual walk-in closets, and en-suite bath complete with dual sinks, garden tub, walk-in shower, and water closet. Sliding glass doors lead from the great room to the screen enclosed, covered lanai, with ample space to grill, entertain, and dine. Experience peace of mind as this home has motorized storm shutters, and a 22 KW Generac generator that comes with a transferable warranty until 2028. HVAC 2020 with a 10-year warranty and whole house water softener with reverse osmosis. Low HOA fees include high speed internet, Direct TV streaming, yard maintenance, irrigation, and access to the community amenities inclusive of the heated pool and spa, fitness center, pickleball, basketball, and playground. Conveniently near beautiful Gulf beaches, Oscar Scherer State Park, Legacy Bicycle Trail, Pine View School, a variety of waterfront restaurants, and shopping.

649 Crane Prairie Way, Osprey/Nokomis

$1,049,000

Welcome to 366 South Creek Court, located in the highly sought-after gated waterfront community of South Creek in Osprey, Florida. Nearly completely renovated, this beautiful 4-bedroom, 3-bathroom home offers 2,775 square feet of thoughtfully designed living space, combining elegant finishes, comfortable living spaces, and exceptional indoor-outdoor living. The open and bright floor plan features separate living and dining areas, a spacious family room, and a charming dinette overlooking the lanai and backyard. Luxury details throughout include tray ceilings, crown molding, rounded wall edges, plantation shutters, 8-foot doors, arched doorways, and engineered hardwood flooring. Fresh interior paint and expansive windows and doors fill the home with natural light. At the heart of the home is the beautifully renovated kitchen, featuring 42-inch shaker-style soft-close cabinetry with crown molding, deep drawers, stainless steel appliances, induction cooking, a hood vent, dual-bowl sink, and quality hardware. Vibrant quartz countertops and an oversized island with seating create an inviting space for everyday living and entertaining. The front living area provides a welcoming setting for conversation or relaxing with a book beside the electric fireplace with solid wood mantel. Adjacent to the living space is a dedicated dining area with a wet bar and wine chiller, ideal for entertaining family and guests. The spacious primary suite offers abundant natural light and direct access to the screened lanai. The ensuite features dual vanities, a dedicated makeup counter and seat, generous counter space, dual walk-in closets, and a brand-new oversized custom walk-in shower. Three additional guest bedrooms offer excellent closet space and natural light. The first guest bath combines a large walk-in shower with a conveniently located laundry area featuring a stackable washer and dryer. The second guest bath offers a dual vanity, tub/shower combination, and adjacent linen closet. Outdoor living takes center stage with a covered and screened paver lanai featuring a heated pool and spa. The lush, mature landscaping and areca palm-lined backyard provide a private and tranquil setting. An additional exterior patio has been designed to accommodate a 72-inch outdoor kitchen, creating an ideal space for entertaining. The home welcomes guests with a paver driveway and sidewalk leading to a charming country-style front porch. The oversized two-car extended garage features ceiling storage racks, a side-entry door, and a hurricane-rated garage door. Additional exterior improvements include fresh paint, new lighting, security cameras, beautiful landscaping, an irrigation system, and hurricane storm panels for every opening. South Creek offers a low HOA fee and an exceptional collection of amenities, including a kayak launch, tennis and pickleball courts, basketball court, and community boat and fishing dock on the South Creek saltwater canal. Ideally located near Casey Key, Nokomis and Siesta Key beaches, Pine View School, shopping, restaurants, a dog park, and the Legacy Trail. Located in an X flood zone, flood insurance is optional. This beautifully renovated South Creek home offers the perfect combination of style, privacy, amenities, and coastal Florida living.

4 Beds ⋅ 3 Baths ⋅ A4708943 MLS

Welcome to 366 South Creek Court, located in the highly sought-after gated waterfront community of South Creek in Osprey, Florida. Nearly completely renovated, this beautiful 4-bedroom, 3-bathroom home offers 2,775 square feet of thoughtfully designed living space, combining elegant finishes, comfortable living spaces, and exceptional indoor-outdoor living. The open and bright floor plan features separate living and dining areas, a spacious family room, and a charming dinette overlooking the lanai and backyard. Luxury details throughout include tray ceilings, crown molding, rounded wall edges, plantation shutters, 8-foot doors, arched doorways, and engineered hardwood flooring. Fresh interior paint and expansive windows and doors fill the home with natural light. At the heart of the home is the beautifully renovated kitchen, featuring 42-inch shaker-style soft-close cabinetry with crown molding, deep drawers, stainless steel appliances, induction cooking, a hood vent, dual-bowl sink, and quality hardware. Vibrant quartz countertops and an oversized island with seating create an inviting space for everyday living and entertaining. The front living area provides a welcoming setting for conversation or relaxing with a book beside the electric fireplace with solid wood mantel. Adjacent to the living space is a dedicated dining area with a wet bar and wine chiller, ideal for entertaining family and guests. The spacious primary suite offers abundant natural light and direct access to the screened lanai. The ensuite features dual vanities, a dedicated makeup counter and seat, generous counter space, dual walk-in closets, and a brand-new oversized custom walk-in shower. Three additional guest bedrooms offer excellent closet space and natural light. The first guest bath combines a large walk-in shower with a conveniently located laundry area featuring a stackable washer and dryer. The second guest bath offers a dual vanity, tub/shower combination, and adjacent linen closet. Outdoor living takes center stage with a covered and screened paver lanai featuring a heated pool and spa. The lush, mature landscaping and areca palm-lined backyard provide a private and tranquil setting. An additional exterior patio has been designed to accommodate a 72-inch outdoor kitchen, creating an ideal space for entertaining. The home welcomes guests with a paver driveway and sidewalk leading to a charming country-style front porch. The oversized two-car extended garage features ceiling storage racks, a side-entry door, and a hurricane-rated garage door. Additional exterior improvements include fresh paint, new lighting, security cameras, beautiful landscaping, an irrigation system, and hurricane storm panels for every opening. South Creek offers a low HOA fee and an exceptional collection of amenities, including a kayak launch, tennis and pickleball courts, basketball court, and community boat and fishing dock on the South Creek saltwater canal. Ideally located near Casey Key, Nokomis and Siesta Key beaches, Pine View School, shopping, restaurants, a dog park, and the Legacy Trail. Located in an X flood zone, flood insurance is optional. This beautifully renovated South Creek home offers the perfect combination of style, privacy, amenities, and coastal Florida living.

366 S Creek Court, Osprey/Nokomis

120 Villa Drive Unit 120, Osprey/Nokomis

$465,000

FULLY FURNISHED WATERFRONT VILLA • PRIVATE DOCK WITH 10,000-LB BOAT LIFT • NO FIXED BRIDGES • DIRECT ACCESS TO THE INTRACOASTAL WATERWAY & GULF OF AMERICA! BRING YOUR BOAT AND START LIVING THE FLORIDA WATERFRONT LIFESTYLE! Welcome to this fully furnished, 2-bedroom, 2-bath waterfront villa in Sorrento Villas, offering an exceptional boating opportunity with NO FIXED BRIDGES between your private dock and the Intracoastal Waterway! Featuring a private dock, 10,000-lb boat lift and unobstructed bridge clearance to the ICW, this property is especially appealing to boating enthusiasts seeking convenient access for larger vessels. Cruise the Intracoastal Waterway, head into the Gulf of America, explore Siesta Key and Midnight Pass, or spend the afternoon discovering waterfront restaurants and nearby coastal destinations. With your boat just steps from your back door, the Florida boating lifestyle is yours to enjoy! Inside, discover 1,404 square feet of inviting living space, offered FULLY FURNISHED for a convenient, turnkey transition to waterfront living. The open floor plan features tile flooring, a spacious living area and an updated kitchen with wood cabinetry, granite countertops, stainless steel appliances, a large island and an extended breakfast bar. A natural stone accent wall adds character, while expansive windows and glass doors fill the living areas with natural light and showcase the waterfront setting. Outdoor living is where this property truly shines! Step onto your screened lanai and enjoy peaceful canal views, tropical landscaping and the coastal breeze. Just beyond the lanai, a limestone walkway leads to your waterfront patio and private dock, creating an inviting setting for morning coffee, afternoon relaxation or evening conversations overlooking the water. Boating enthusiasts will appreciate the updated dock, 10,000-lb boat lift, dedicated fish-cleaning station and updated water and electrical connections. The dock approach has also been raised with additional cement. Numerous improvements include a new electrical panel and breakers, new lanai screening, rain gutters, updated landscaping, a new garage door motor, track and keypad, luxury vinyl plank flooring in the primary bedroom and an updated kitchen faucet. Additional features include hurricane shutters, a tile roof installed in 2009, an A/C system installed in 2015 and an attached garage. Ideally located in Osprey between Sarasota and Venice, this waterfront retreat offers convenient access to Siesta Key, Nokomis Beach, Oscar Scherer State Park, shopping, dining and outdoor recreation. FULLY FURNISHED AND READY FOR YOUR NEXT CHAPTER! With no fixed bridges to the Intracoastal Waterway, direct boating access to the Gulf of America, a private dock and a 10,000-lb boat lift, this property offers the freedom to explore Southwest Florida's waterways right from your backyard. YOUR BOAT. YOUR DOCK. YOUR GATEWAY TO THE GULF!

2 Beds ⋅ 2 Baths ⋅ A4708477 MLS

FULLY FURNISHED WATERFRONT VILLA • PRIVATE DOCK WITH 10,000-LB BOAT LIFT • NO FIXED BRIDGES • DIRECT ACCESS TO THE INTRACOASTAL WATERWAY & GULF OF AMERICA! BRING YOUR BOAT AND START LIVING THE FLORIDA WATERFRONT LIFESTYLE! Welcome to this fully furnished, 2-bedroom, 2-bath waterfront villa in Sorrento Villas, offering an exceptional boating opportunity with NO FIXED BRIDGES between your private dock and the Intracoastal Waterway! Featuring a private dock, 10,000-lb boat lift and unobstructed bridge clearance to the ICW, this property is especially appealing to boating enthusiasts seeking convenient access for larger vessels. Cruise the Intracoastal Waterway, head into the Gulf of America, explore Siesta Key and Midnight Pass, or spend the afternoon discovering waterfront restaurants and nearby coastal destinations. With your boat just steps from your back door, the Florida boating lifestyle is yours to enjoy! Inside, discover 1,404 square feet of inviting living space, offered FULLY FURNISHED for a convenient, turnkey transition to waterfront living. The open floor plan features tile flooring, a spacious living area and an updated kitchen with wood cabinetry, granite countertops, stainless steel appliances, a large island and an extended breakfast bar. A natural stone accent wall adds character, while expansive windows and glass doors fill the living areas with natural light and showcase the waterfront setting. Outdoor living is where this property truly shines! Step onto your screened lanai and enjoy peaceful canal views, tropical landscaping and the coastal breeze. Just beyond the lanai, a limestone walkway leads to your waterfront patio and private dock, creating an inviting setting for morning coffee, afternoon relaxation or evening conversations overlooking the water. Boating enthusiasts will appreciate the updated dock, 10,000-lb boat lift, dedicated fish-cleaning station and updated water and electrical connections. The dock approach has also been raised with additional cement. Numerous improvements include a new electrical panel and breakers, new lanai screening, rain gutters, updated landscaping, a new garage door motor, track and keypad, luxury vinyl plank flooring in the primary bedroom and an updated kitchen faucet. Additional features include hurricane shutters, a tile roof installed in 2009, an A/C system installed in 2015 and an attached garage. Ideally located in Osprey between Sarasota and Venice, this waterfront retreat offers convenient access to Siesta Key, Nokomis Beach, Oscar Scherer State Park, shopping, dining and outdoor recreation. FULLY FURNISHED AND READY FOR YOUR NEXT CHAPTER! With no fixed bridges to the Intracoastal Waterway, direct boating access to the Gulf of America, a private dock and a 10,000-lb boat lift, this property offers the freedom to explore Southwest Florida's waterways right from your backyard. YOUR BOAT. YOUR DOCK. YOUR GATEWAY TO THE GULF!

120 Villa Drive Unit 120, Osprey/Nokomis

$1,445,000

Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership.

3 Beds ⋅ 4 Baths ⋅ A4707058 MLS

Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership.

422 Blue Garden Lane, Osprey/Nokomis

168 Coastal Hammock Court, Osprey/Nokomis

$1,900,000

Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

3 Beds ⋅ 4 Baths ⋅ A4707893 MLS

Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

168 Coastal Hammock Court, Osprey/Nokomis

$4,590,000

Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

5 Beds ⋅ 5 Baths ⋅ A4707430 MLS

Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey/Nokomis

$3,700,000

This custom-built 2024 masterpiece was thoughtfully designed to deliver the perfect balance of luxury, functionality, and effortless indoor-outdoor living. Positioned to capture sweeping views of the 6th and 7th holes of the Heron Course, the home showcases exceptional craftsmanship and attention to detail at every turn. From the moment you arrive, the impressive 10 foot hurricane-rated steel front door, circular driveway, and beautiful exterior create a lasting first impression. Inside, wood-look tile flooring flows throughout. The expansive open concept layout seamlessly connects the main living spaces while still offering dedicated rooms for privacy and everyday comfort. The designer kitchen is a true showpiece, featuring a custom range hood, pot filler, oversized refrigerator, and premium finishes that cater to both casual family meals and formal entertaining. The large master suite is a study in elegance. The luxurious master bath is the pinnacle of luxury, with dual sinks, a lighted stand alone make up table, claw foot tub, huge steam shower, expansive countertop and storage space along with custom lighting. The upstairs loft is a great addition for those who love to entertain and host guests. It has a bedroom, bathroom, and living area with a bar and a balcony providing lovely views over the pool. Step outside to a truly exceptional outdoor retreat where luxury and tranquility come together in a breathtaking setting. The resort-style pool and spa serve as the centerpiece of the home's outdoor living experience. Designed for both relaxation and entertaining, this private oasis features expansive lounging areas, an incredible outdoor kitchen, and seamless indoor-outdoor connectivity through hurricane-rated bifold sliders that open the home to the stunning golf course backdrop. Built not only for beauty, but also for convenience and peace of mind, the home is equipped with premium hurricane-rated windows and bifold sliders, spray foam insulation, central vacuum, automated lighting and climate control systems, and wiring for a generator. Everyday functionality is enhanced by a dedicated mudroom, spacious laundry room, climate-controlled storage, and a four-car garage complete with epoxy floors, custom storage solutions, and additional space for a gym or workout area. shaded dining, and a sun-splashed pool and spa area under a screened enclosure. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership.

4 Beds ⋅ 4 Baths ⋅ A4707301 MLS

This custom-built 2024 masterpiece was thoughtfully designed to deliver the perfect balance of luxury, functionality, and effortless indoor-outdoor living. Positioned to capture sweeping views of the 6th and 7th holes of the Heron Course, the home showcases exceptional craftsmanship and attention to detail at every turn. From the moment you arrive, the impressive 10 foot hurricane-rated steel front door, circular driveway, and beautiful exterior create a lasting first impression. Inside, wood-look tile flooring flows throughout. The expansive open concept layout seamlessly connects the main living spaces while still offering dedicated rooms for privacy and everyday comfort. The designer kitchen is a true showpiece, featuring a custom range hood, pot filler, oversized refrigerator, and premium finishes that cater to both casual family meals and formal entertaining. The large master suite is a study in elegance. The luxurious master bath is the pinnacle of luxury, with dual sinks, a lighted stand alone make up table, claw foot tub, huge steam shower, expansive countertop and storage space along with custom lighting. The upstairs loft is a great addition for those who love to entertain and host guests. It has a bedroom, bathroom, and living area with a bar and a balcony providing lovely views over the pool. Step outside to a truly exceptional outdoor retreat where luxury and tranquility come together in a breathtaking setting. The resort-style pool and spa serve as the centerpiece of the home's outdoor living experience. Designed for both relaxation and entertaining, this private oasis features expansive lounging areas, an incredible outdoor kitchen, and seamless indoor-outdoor connectivity through hurricane-rated bifold sliders that open the home to the stunning golf course backdrop. Built not only for beauty, but also for convenience and peace of mind, the home is equipped with premium hurricane-rated windows and bifold sliders, spray foam insulation, central vacuum, automated lighting and climate control systems, and wiring for a generator. Everyday functionality is enhanced by a dedicated mudroom, spacious laundry room, climate-controlled storage, and a four-car garage complete with epoxy floors, custom storage solutions, and additional space for a gym or workout area. shaded dining, and a sun-splashed pool and spa area under a screened enclosure. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership.

650 Oaks Creek Court, Osprey/Nokomis

$540,000

Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

3 Beds ⋅ 2 Baths ⋅ A4707282 MLS

Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, Osprey/Nokomis

$1,399,000

This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

3 Beds ⋅ 3 Baths ⋅ A4707187 MLS

This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

256 Sugar Mill, Osprey/Nokomis

$3,700,000

Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

5 Beds ⋅ 5 Baths ⋅ A4706333 MLS

Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey/Nokomis

$1,295,000

Impeccable is the only way to describe this charming property! This stunning 3 bedroom, 2 bathroom residence has been completely remodeled to create a luxurious yet comfortable, livable home. No detail has been overlooked in the complete renovation, making it truly gorgeous and unique. The interior is incredible and has so many high-end features; tile flooring designed to look like wood, quartzite countertops, a stylish coffee bar, and a beautifully crafted hood vent. The recent addition of an entire deck off to the side of the home enhances the outdoor living space. The deck includes a canopy that extends to cover part of the area, providing shade for the dining table, swinging chair, and grill. Additionally, a hot tub has been added for your relaxation. The home boasts three bedrooms, with one currently being used as an office. The previously enclosed Florida room has been transformed into a spacious family room, perfect for gatherings. The interior design, crafted by a professional, ensures that no detail no matter how big or small has been missed. The property also features a huge yard, the largest in the neighborhood, providing ample space for outdoor activities, and the pièce de résistance, a dreamy view of the pond. Residents enjoy access to a community pool and clubhouse, both within walking distance from the house. Plus, landscape maintenance is included, making it a hassle-free living experience. With mandatory membership, residents can enjoy all the amenities The Oaks offers. There is currently no waiting list for either Golf or Sports/Social membership.

3 Beds ⋅ 2 Baths ⋅ A4706711 MLS

Impeccable is the only way to describe this charming property! This stunning 3 bedroom, 2 bathroom residence has been completely remodeled to create a luxurious yet comfortable, livable home. No detail has been overlooked in the complete renovation, making it truly gorgeous and unique. The interior is incredible and has so many high-end features; tile flooring designed to look like wood, quartzite countertops, a stylish coffee bar, and a beautifully crafted hood vent. The recent addition of an entire deck off to the side of the home enhances the outdoor living space. The deck includes a canopy that extends to cover part of the area, providing shade for the dining table, swinging chair, and grill. Additionally, a hot tub has been added for your relaxation. The home boasts three bedrooms, with one currently being used as an office. The previously enclosed Florida room has been transformed into a spacious family room, perfect for gatherings. The interior design, crafted by a professional, ensures that no detail no matter how big or small has been missed. The property also features a huge yard, the largest in the neighborhood, providing ample space for outdoor activities, and the pièce de résistance, a dreamy view of the pond. Residents enjoy access to a community pool and clubhouse, both within walking distance from the house. Plus, landscape maintenance is included, making it a hassle-free living experience. With mandatory membership, residents can enjoy all the amenities The Oaks offers. There is currently no waiting list for either Golf or Sports/Social membership.

17 Bayhead Lane, Osprey/Nokomis

$655,000

Welcome to 700 Shadow Bay Way, an impressive 3-bedroom, 2.5-bath pool home with a den, 3-car garage and more than 2,500 square feet of living space in the highly desirable Woodlands at Rivendell. Set on an oversized corner lot, this spacious home offers a bright, open and functional floor plan with high ceilings, crown molding, a generous great room and a separate dining area ideal for both everyday living and entertaining. The den provides valuable additional space for a home office, library or possible fourth bedroom. The spacious eat-in kitchen offers abundant cabinetry and counter space, a breakfast bar, walk-in pantry and an open connection to the main living areas. The private primary suite includes direct access to the lanai, two walk-in closets and an ensuite bath with dual vanities, soaking tub and separate shower. Step outside to an expansive screened lanai surrounding the pool and spa, with a covered seating area and plenty of room to relax or entertain. Additional highlights include a split-bedroom layout, inside laundry, brick-paver driveway and walkway, mature landscaping and an attached 3-car garage. Rivendell is known for its tree-lined streets, lakes and natural surroundings, with a convenient Osprey location near Pine View School, Oscar Scherer State Park, shopping, dining, Gulf beaches, Venice and Sarasota. A wonderful opportunity to enjoy generous living space, a private pool and the Florida lifestyle in one of Osprey's established communities.

3 Beds ⋅ 3 Baths ⋅ O6442446 MLS

Welcome to 700 Shadow Bay Way, an impressive 3-bedroom, 2.5-bath pool home with a den, 3-car garage and more than 2,500 square feet of living space in the highly desirable Woodlands at Rivendell. Set on an oversized corner lot, this spacious home offers a bright, open and functional floor plan with high ceilings, crown molding, a generous great room and a separate dining area ideal for both everyday living and entertaining. The den provides valuable additional space for a home office, library or possible fourth bedroom. The spacious eat-in kitchen offers abundant cabinetry and counter space, a breakfast bar, walk-in pantry and an open connection to the main living areas. The private primary suite includes direct access to the lanai, two walk-in closets and an ensuite bath with dual vanities, soaking tub and separate shower. Step outside to an expansive screened lanai surrounding the pool and spa, with a covered seating area and plenty of room to relax or entertain. Additional highlights include a split-bedroom layout, inside laundry, brick-paver driveway and walkway, mature landscaping and an attached 3-car garage. Rivendell is known for its tree-lined streets, lakes and natural surroundings, with a convenient Osprey location near Pine View School, Oscar Scherer State Park, shopping, dining, Gulf beaches, Venice and Sarasota. A wonderful opportunity to enjoy generous living space, a private pool and the Florida lifestyle in one of Osprey's established communities.

700 Shadow Bay Way, Osprey/Nokomis

$1,590,000

Located behind the gates of The Oaks Clubside and within close proximity to the clubhouse, this 3-bedroom plus office, 3.5-bath residence offers over 3,500 square feet of refined, comfortable living. Positioned on the 4th hole of the Eagle Course, the home features expansive golf views enjoyed from the screened lanai with pool and spa. The interior includes an elegant formal living room with fireplace, formal dining room, a spacious master suite with an oversized walk-in closet, a large laundry room, tray ceilings, crown molding, ceiling fans. This home has a whole-house generator, hurricane protection. a NEW ROOF and NEW HVAC. An oversized 3-car garage and circular paver driveway complete the property, providing everything needed to enjoy refined country club lifestyle The Oaks offers. The club’s amenities include two championship golf courses, pickleball courts, 14 Har-Tru courts and a croquet court, exceptional culinary experiences and a robust social calendar. Required with homeownership, there is currently no waiting list for either Golf or Sports/Social membership.

3 Beds ⋅ 4 Baths ⋅ A4706228 MLS

Located behind the gates of The Oaks Clubside and within close proximity to the clubhouse, this 3-bedroom plus office, 3.5-bath residence offers over 3,500 square feet of refined, comfortable living. Positioned on the 4th hole of the Eagle Course, the home features expansive golf views enjoyed from the screened lanai with pool and spa. The interior includes an elegant formal living room with fireplace, formal dining room, a spacious master suite with an oversized walk-in closet, a large laundry room, tray ceilings, crown molding, ceiling fans. This home has a whole-house generator, hurricane protection. a NEW ROOF and NEW HVAC. An oversized 3-car garage and circular paver driveway complete the property, providing everything needed to enjoy refined country club lifestyle The Oaks offers. The club’s amenities include two championship golf courses, pickleball courts, 14 Har-Tru courts and a croquet court, exceptional culinary experiences and a robust social calendar. Required with homeownership, there is currently no waiting list for either Golf or Sports/Social membership.

402 Macewen Drive, Osprey/Nokomis

$1,700,000

Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thoughtful design throughout. Behind the gates of The Oaks Bayside, it is beautifully situated, set back on a lot that offers peace and privacy. The open kitchen is a home chef’s dream and serves as the centerpiece of the home. Showcasing custom cabinetry, expansive counter space, and high-end appliances, the layout is ideal for both everyday cooking and effortless entertaining. There is a breakfast bar, dinette that is flooded by filtered sunshine through the tinted aquarium window, as well as a formal dining room. The living spaces flow seamlessly, enhanced by abundant natural light and refined finishes that elevate the home’s incredible appeal. The master suite has extra insulation between the great room and the master bedroom wall, ensuring a quiet, private sanctuary. The room is spacious and features a spa-like master bath with a tub, large separate walk-in shower, dual sinks and an abundance of mirrors and lighting. Step outside to a lovely lanai, with pool, spa and outdoor kitchen. This space is perfectly designed for relaxing, hosting gatherings, or enjoying the tranquil Florida lifestyle year-round. This gorgeous home offers so much, you truly must see it to fully appreciate it! Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

3 Beds ⋅ 3 Baths ⋅ A4705716 MLS

Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thoughtful design throughout. Behind the gates of The Oaks Bayside, it is beautifully situated, set back on a lot that offers peace and privacy. The open kitchen is a home chef’s dream and serves as the centerpiece of the home. Showcasing custom cabinetry, expansive counter space, and high-end appliances, the layout is ideal for both everyday cooking and effortless entertaining. There is a breakfast bar, dinette that is flooded by filtered sunshine through the tinted aquarium window, as well as a formal dining room. The living spaces flow seamlessly, enhanced by abundant natural light and refined finishes that elevate the home’s incredible appeal. The master suite has extra insulation between the great room and the master bedroom wall, ensuring a quiet, private sanctuary. The room is spacious and features a spa-like master bath with a tub, large separate walk-in shower, dual sinks and an abundance of mirrors and lighting. Step outside to a lovely lanai, with pool, spa and outdoor kitchen. This space is perfectly designed for relaxing, hosting gatherings, or enjoying the tranquil Florida lifestyle year-round. This gorgeous home offers so much, you truly must see it to fully appreciate it! Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

141 Sugar Mill Drive, Osprey/Nokomis

$1,399,000

Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

4 Beds ⋅ 4 Baths ⋅ A4705553 MLS

Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, Osprey/Nokomis

$749,900

Virtually Staged. Welcome to your ultimate lakeside maintenance free sanctuary! Seller is offering Roof Credit to buyer. This home is nestled in a premier community renowned for its top-rated gifted school district, this expanded floor plan in the Willow Bend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, and ceiling fans. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-rated, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

3 Beds ⋅ 2 Baths ⋅ A4705435 MLS

Virtually Staged. Welcome to your ultimate lakeside maintenance free sanctuary! Seller is offering Roof Credit to buyer. This home is nestled in a premier community renowned for its top-rated gifted school district, this expanded floor plan in the Willow Bend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, and ceiling fans. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-rated, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

1328 Thornapple Drive, Osprey/Nokomis

$565,000

Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The fishing here is easy and the setting couldn't be more scenic. The home offers 3 bedrooms and 2 baths, with the primary suite privately situated on the entire second floor featuring a spacious walk-in closet and abundant storage. Downstairs, heart pine flooring flows through the living area, warmed by a cozy wood-burning fireplace on cooler evenings. A screened wraparound porch on the first level extends your living space outdoors, ideal for morning coffee or evening breezes off the creek. This home is ready for your personal touch and is an incredible opportunity to update and build instant equity in a location that can't be replicated. The elevated design offers peace of mind along with sweeping views of the creek and surrounding woods. Outside, the yard is a true nature lover's dream--idyllic and alive with birdsong, from herons to osprey, all just steps from your door.

3 Beds ⋅ 2 Baths ⋅ A4705136 MLS

Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The fishing here is easy and the setting couldn't be more scenic. The home offers 3 bedrooms and 2 baths, with the primary suite privately situated on the entire second floor featuring a spacious walk-in closet and abundant storage. Downstairs, heart pine flooring flows through the living area, warmed by a cozy wood-burning fireplace on cooler evenings. A screened wraparound porch on the first level extends your living space outdoors, ideal for morning coffee or evening breezes off the creek. This home is ready for your personal touch and is an incredible opportunity to update and build instant equity in a location that can't be replicated. The elevated design offers peace of mind along with sweeping views of the creek and surrounding woods. Outside, the yard is a true nature lover's dream--idyllic and alive with birdsong, from herons to osprey, all just steps from your door.

2046 Cordes Street, Osprey/Nokomis

$950,000

Huge Opportunity – Three Homes – Motivated Seller! Outstanding opportunity to acquire three homes in one transaction in a rapidly developing Osprey area. The properties are located close to the proposed Margaritaville Resort, which is expected to become a major destination in the area and has been proposed to include ferry service providing access to Siesta Key. This location is already generating significant attention, with increasing interest in the surrounding area. All three homes are substantially completed, giving a buyer the opportunity to take over the project without starting from the ground up. The homes will require additional construction and finishing work, and a contractor will be needed to complete the remaining items necessary to obtain the required Certificates of Occupancy. For the right buyer, this creates an opportunity to complete all three properties and determine the best strategy moving forward. Finish and sell the homes individually, hold them as investment properties, use them as long-term rentals, or ptentially sell them off separately for what could be a large profit. Much of the heavy lifting has already been done, allowing an experienced investor, builder, or contractor to focus on completing the project and unlocking the potential value of the properties.

3 Beds ⋅ 2 Baths ⋅ A4704911 MLS

Huge Opportunity – Three Homes – Motivated Seller! Outstanding opportunity to acquire three homes in one transaction in a rapidly developing Osprey area. The properties are located close to the proposed Margaritaville Resort, which is expected to become a major destination in the area and has been proposed to include ferry service providing access to Siesta Key. This location is already generating significant attention, with increasing interest in the surrounding area. All three homes are substantially completed, giving a buyer the opportunity to take over the project without starting from the ground up. The homes will require additional construction and finishing work, and a contractor will be needed to complete the remaining items necessary to obtain the required Certificates of Occupancy. For the right buyer, this creates an opportunity to complete all three properties and determine the best strategy moving forward. Finish and sell the homes individually, hold them as investment properties, use them as long-term rentals, or ptentially sell them off separately for what could be a large profit. Much of the heavy lifting has already been done, allowing an experienced investor, builder, or contractor to focus on completing the project and unlocking the potential value of the properties.

210 Patterson Avenue, Osprey/Nokomis

$9,750,000

At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

5 Beds ⋅ 8 Baths ⋅ A4704643 MLS

At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

1216 N Casey Key Road, Osprey/Nokomis

$1,495,000

Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities and driving ranges. The member-owned Oaks Club features a 34,000-square-foot clubhouse with multiple dining venues, tennis courts, pickleball courts,a resort-style pool, and a 7,500-square-foot fitness center. Beyond the community gates, this location provides convenient access to Gulf Coast beaches, scenic trails including The Legacy Trail, local parks, as well as the cultural offerings of Sarasota and Venice. Schedule a private tour to explore the property and experience the distinct lifestyle of The Oaks Club.

3 Beds ⋅ 3 Baths ⋅ A4704489 MLS

Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities and driving ranges. The member-owned Oaks Club features a 34,000-square-foot clubhouse with multiple dining venues, tennis courts, pickleball courts,a resort-style pool, and a 7,500-square-foot fitness center. Beyond the community gates, this location provides convenient access to Gulf Coast beaches, scenic trails including The Legacy Trail, local parks, as well as the cultural offerings of Sarasota and Venice. Schedule a private tour to explore the property and experience the distinct lifestyle of The Oaks Club.

226 Saint James Park, Osprey/Nokomis

$2,095,000

Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

4 Beds ⋅ 4 Baths ⋅ TB8543439 MLS

Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

154 Lookout Point Drive, Osprey/Nokomis

$1,100,000

Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.

5 Beds ⋅ 4 Baths ⋅ A4704317 MLS

Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.

296 Pine Ranch Trail, Osprey/Nokomis

$699,000

Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

3 Beds ⋅ 2 Baths ⋅ A4701662 MLS

Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

299 Turquoise Lane, Osprey/Nokomis

$630,000

Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

4 Beds ⋅ 2 Baths ⋅ A4701532 MLS

Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

1036 Oak Meadow Lane, Osprey/Nokomis

$1,690,000

Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

3 Beds ⋅ 2 Baths ⋅ A4695429 MLS

Imagine starting your morning with coffee beside your private courtyard pool, opening the sliders to the Florida sunshine and ending the day with friends gathered around the kitchen island before heading out by golf cart for dinner or a sunset near the water. Welcome to 206 Four Knot Lane, a beautifully updated, move-in-ready home in Southbay Yacht & Racquet Club, one of Osprey’s most desirable waterfront marina communities. At the heart of the home is an impressive 14' x 37' heated pool, framed on three sides by the residence and visible from multiple living spaces. Several rooms open directly to the covered lanais and pool area, creating a private courtyard-style setting and a seamless connection between indoor and outdoor living. Inside, the 2,411-square-foot residence offers 3 bedrooms, 2 baths, an office/den, spacious living areas, and a thoughtfully designed split floor plan. Floor-to-ceiling impact-rated windows and sliders installed in 2020 fill the home with natural light and showcase the pool from throughout the main living spaces. The primary suite is privately positioned and includes an adjoining office/den and ensuite bath with soaking tub and custom cabinetry. Two additional bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed provides added flexibility for overnight guests or workspace. The home has been extensively updated with 12" x 72" Ceramica Sant’Agostino Italian porcelain plank tile flooring in Barkwood Ash, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint completed in 2025. The chef-inspired kitchen is designed for both everyday living and entertaining, with new custom cabinetry, quartz countertops, high-end 2025 GE Monogram appliances, a 48-inch refrigerator, induction cooktop, wall oven/microwave, built-in wine refrigerator, excellent storage, and a large center island with seating for 8–10. The adjoining dining area features an integrated bar with custom cabinetry and a fireplace ready for an insert. Additional highlights include dual-zone A/C systems installed in 2025, new Electrolux stackable washer and dryer, a spacious laundry room with utility sink and coffee/tea bar, concrete tile roof installed in 2020, re-plumbing completed in 2007, an oversized 2-car garage with epoxy flooring and custom storage, mature tropical landscaping with irrigation, and a private outdoor shower. There is also potential to add a fourth bedroom with ensuite bath or create additional garage/storage space. Southbay Yacht & Racquet Club offers a true Florida lifestyle with a private 172-slip deep-water marina accommodating vessels up to approximately 58 feet, along with a clubhouse, fitness center, heated community pool and spa, tennis, pickleball, basketball, bocce, playground, kayak launch and storage, jet ski pads, low HOA fees, and an active social atmosphere. The golf-cart-friendly community provides convenient access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, tiki bars, and everything that makes Florida’s Gulf Coast lifestyle so appealing. Interior and exterior furnishings, artwork, televisions, potted plants, outdoor gas grill, and pizza oven are available separately by bill of sale. If you have been searching for a beautifully updated home where the pool, the home, the marina, and the Florida lifestyle all come together, 206 Four Knot Lane deserves to be seen in person.

206 Four Knot Lane, Osprey/Nokomis

$1,595,000

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

4 Beds ⋅ 4 Baths ⋅ A4695145 MLS

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey/Nokomis

$1,495,000

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

3 Beds ⋅ 4 Baths ⋅ A4695959 MLS

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey/Nokomis

$4,790,000

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

4 Beds ⋅ 6 Baths ⋅ A4694716 MLS

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey/Nokomis

$699,000

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

3 Beds ⋅ 2 Baths ⋅ A4694468 MLS

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.

103 Bishops Court Road, Osprey/Nokomis