Osprey Homes with Playground Community Features

Osprey Homes with Playground Community Features

Welcome to Osprey, Florida – a hidden gem nestled in the heart of Sarasota County, where the sun-kissed beaches meet the serene charm of coastal living. This picturesque community, straddling the line between Osprey and Nokomis, offers a delightful blend of natural beauty, vibrant culture, and a family-friendly atmosphere that makes it an ideal place to call home.

Osprey is known for its stunning landscapes and rich history, with nearby attractions like the Oscar Scherer State Park, where residents can enjoy hiking, biking, and birdwatching in a lush, natural setting. The community is also just a stone's throw away from the sparkling shores of Nokomis Beach, perfect for sunbathing, swimming, and collecting seashells.

For families seeking a nurturing environment, Osprey offers homes within communities that feature playgrounds, ensuring that children have safe and engaging spaces to play and explore. These family-friendly amenities foster a sense of community and connection among neighbors, making it easy to build lasting friendships.

In addition to its outdoor attractions, Osprey boasts a variety of dining, shopping, and cultural experiences. From quaint local eateries to upscale dining options, there’s something to satisfy every palate. The nearby Sarasota area is rich in art and culture, with galleries, theaters, and festivals that celebrate the vibrant local scene.

Whether you’re looking for a cozy family home or a luxurious retreat, Osprey’s diverse real estate options cater to all lifestyles. Discover the charm of Osprey, where community, nature, and family come together in perfect harmony.

Newest Osprey Homes with Playground Community Features

102 Windward Drive, Osprey/Nokomis
$1,047,000
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

366 S Creek Court, Osprey/Nokomis
$1,049,000
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

401 N Point Road Unit 703, Osprey/Nokomis
$1,200,000
3 Beds ⋅ 3 Baths ⋅ A4707244 MLS ⋅ Meridian 3 BLDG.
Enjoy spectacular Gulf sunsets from this Move-In Ready, Fully Renovated 7th-floor condominium residence featuring 3-Bedrooms, 3-Full-Baths and over 2,200 square feet of beautifully designed living space with an open floor plan ideal for both everyday living and entertaining. The thoughtfully updated kitchen features quartz countertops, stainless steel appliances, Sub-Zero refrigeration, a wine refrigerator, and an Invisacook® invisible induction cooktop, creating a sleek and highly functional culinary space. The spacious private balcony offers tranquil preserve views and abundant opportunities for wildlife watching. Additional highlights include two assigned parking spaces and an exceptional combination of expansive views, privacy, modern finishes, and coastal living. A new HVAC system adds to the convenience and peace of mind. A must-see property! Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. Meridian Tower #3 also features a new roof (2025). 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

401 N Point Road Unit 703, Osprey/Nokomis

275 Lookout Point Drive, Osprey/Nokomis
$4,590,000
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

324 Osprey Point Drive, Osprey/Nokomis
$3,700,000
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

700 Shadow Bay Way, Osprey/Nokomis
$655,000
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

1417 Landview Lane, Osprey/Nokomis
$1,349,999
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

409 N Point Road Unit 803, Osprey/Nokomis
$985,000
3 Beds ⋅ 3 Baths ⋅ A4703407 MLS ⋅ Meridian Iv BLDG.
ENJOY BREATHTAKING SUNSET VIEWS ACROSS LITTLE SARASOTA BAY AND THE GULF FROM THIS STUNNING 8TH-FLOOR PENTHOUSE! This exceptional 2,203SF Condominium offers 3 Bedrooms, 3 Full Baths, a coveted Private 2-Car Garage, and the privacy of the highly sought-after, gated Oaks Preserve neighborhood. Arrive through your private elevator foyer and step into a home where panoramic, unobstructed views of Little Sarasota Bay and the Gulf immediately take center stage. Thoughtfully designed with an impressive array of upgrades, the residence features high ceilings, crown molding, hardwood and tile flooring, and a beautifully appointed kitchen with a large island and seating area, granite countertops, stainless steel appliances, solid-wood cabinetry, and ample storage. The spacious Owner’s Suite is a peaceful retreat, complete with a generous walk-in closet, custom-tiled shower, relaxing soaking tub, and dual vanities. Step outside onto the expansive balcony and enjoy a serene setting surrounded by spectacular water views, abundant wildlife, and unforgettable Gulf sunsets. Hurricane-impact windows and sliding doors provide added peace of mind. Climate-controlled storage is conveniently located on the second floor. Residents of Meridian enjoy an array of private amenities, including a heated pool and spa, fitness center, and outdoor grilling area, along with access to the exceptional amenities of The Oaks Club’s main campus. Experience elevated coastal living, spectacular views, privacy, and resort-style amenities—all from this remarkable penthouse at The Oaks. The Oaks Club is a member-owned private golf community with more than 40 years of excellence and is the only private residential golf club in the Sarasota, Bradenton, and Fort Myers region recognized by both Platinum Clubs of America and Distinguished Emerald Clubs of the World. Residents enjoy a magnificent 30,000-square-foot clubhouse, three exceptional dining venues, two championship 18-hole golf courses, outstanding golf instruction, a premier racquet program with 12 Har-Tru HydroGrid tennis courts and pickleball courts, croquet, bocce, basketball, a Junior Olympic swimming pool, and a newly expanded state-of-the-art wellness, fitness, and spa facility. Recognized as "The Healthiest Club" and an Audubon Society-certified community, The Oaks offers an unmatched lifestyle. Ideally located in one of Sarasota County's most sought-after communities, this exceptional residence is just minutes from world-renowned beaches, top-rated schools, fine dining, shopping, and Sarasota's vibrant arts and cultural attractions, making it a rare opportunity to enjoy luxury living in a truly prime location.

409 N Point Road Unit 803, Osprey/Nokomis

206 Four Knot Lane, Osprey/Nokomis
$1,690,000
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

360 N Point Road, Osprey/Nokomis
$1,495,000
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

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