Osprey/Nokomis Homes with Buyer Approval Required Community Features

Osprey/Nokomis Homes with Buyer Approval Required Community Features

Welcome to the charming communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These picturesque towns offer a delightful blend of coastal living, natural beauty, and a warm sense of community. With stunning views of the Gulf of Mexico and easy access to some of the most beautiful beaches in the state, Osprey and Nokomis are ideal for those seeking a serene lifestyle without sacrificing convenience.

Osprey is known for its lush landscapes, historic sites, and vibrant arts scene, while Nokomis boasts a relaxed, laid-back atmosphere perfect for outdoor enthusiasts. Residents enjoy a plethora of recreational activities, from kayaking in the serene waters of the nearby Casey Key to exploring the scenic trails of the Oscar Scherer State Park. Plus, with charming local shops, delicious dining options, and a variety of cultural events, there's always something to enjoy.

In addition to the natural allure, both Osprey and Nokomis feature exclusive homes within Buyer Approval Required communities. These thoughtfully designed neighborhoods offer a range of amenities, ensuring a comfortable and secure living environment. Whether you're looking for a luxurious waterfront property or a cozy retreat, these communities provide a variety of options tailored to fit your lifestyle.

With a focus on community engagement and safety, living in a Buyer Approval Required community allows residents to enjoy a sense of belonging and peace of mind. Discover the enchanting lifestyle that awaits you in Osprey and Nokomis, where your dream home is just a heartbeat away from the beauty of Florida’s Gulf Coast.

Newest Osprey/Nokomis Homes with Buyer Approval Required Community Features

$1,399,000
3 Beds ⋅ 3 Baths ⋅ A4707336 MLS ⋅ 385 BLDG.
Experience the refined country club lifestyle of The Oaks Club in this exceptional waterfront residence within Meridian I at The Oaks Preserve in Osprey. From the moment you step through your private elevator foyer, unobstructed, sweeping water views make an unforgettable first impression. These vistas are beautifully framed from the living and dining areas, kitchen, primary suite, and private study. Step onto the generous balcony, where gentle breezes and breathtaking sunsets set the stage for serene waterfront living. This spacious, maintenance-free residence offers three bedrooms and three baths, including two en-suites, plus a separate den/study and a full laundry room. A private two-car garage beneath the building adds convenience and extra storage. Luxury finishes elevate the interiors, including marble flooring and countertops, stainless steel appliances, crown molding, and custom built-ins. The primary suite is a true retreat, with a sitting area overlooking tranquil water views and a spa-inspired bath featuring dual vanities, a spa tub, and a separate shower. Lovingly maintained by its original owner, the home reflects thoughtful design and pride of ownership throughout. Meridian I residents enjoy a private community pool, fitness center, outdoor grilling area, and on-site maintenance manager, all within the security of The Oaks Preserve's 24-hour guarded gate. Membership in The Oaks Club is required, with a range of membership options and privileges. Renowned for its coastal sophistication, the Club offers refined and casual dining, 36 holes of championship golf, 12 Har-Tru tennis courts, four pickleball courts, a regulation croquet lawn, a state-of-the-art fitness center, a junior Olympic pool, bocce, basketball, a playground, and a vibrant calendar of social and recreational events. Residence 701 at Meridian I is an extraordinary opportunity to embrace Sarasota's premier country club lifestyle, where unmatched amenities meet captivating waterfront views.

385 North Point Road Unit 701, Osprey/Nokomis
$449,000
3 Beds ⋅ 2 Baths ⋅ A4706429 MLS ⋅ Heron Harbor BLDG.
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey/Nokomis
$629,400
3 Beds ⋅ 3 Baths ⋅ A4707579 MLS ⋅ Meridian Vi BLDG.
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS 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. 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. **A MUST SEE**

3603 N Point Road Unit 202, Osprey/Nokomis
$450,000
3 Beds ⋅ 2 Baths ⋅ A4706912 MLS
Virtually Staged. Welcome to 112 Ventosa Place, a beautifully maintained Pembroke model featuring impact windows installed in 2018, located in the gated, resort-style community of Toscana Isles. This single-story home offers 3 bedrooms, 2 baths and approximately 1,804 square feet with an open, light-filled layout designed for comfortable everyday living and entertaining. Inside, high ceilings, crown molding and tile flooring complement the spacious open-concept design. The kitchen flows seamlessly into the dining and great room areas, creating an inviting central gathering space with plenty of room to cook, entertain or simply unwind. Sliding glass doors extend the living space to the screened and covered lanai, offering a peaceful spot for morning coffee, outdoor dining or relaxing at the end of the day. The primary suite features generous walk-in closets and an en-suite bath, while two additional bedrooms and a second full bath provide flexibility for guests, a home office or hobbies. A tile roof, interior laundry room and two-car garage complete the home. Beyond the front door, Toscana Isles offers a true resort-style lifestyle centered around more than 200 acres of lakes and an impressive Tuscan-inspired amenity center. Residents enjoy an approximately 8,000-square-foot clubhouse overlooking the water, infinity-edge heated pool, fitness center, clubroom, tennis, pickleball, bocce, dog park and scenic walking areas. Kayaking, canoeing, paddleboarding and fishing offer even more ways to enjoy the community's interconnected lakes. All of this is just minutes from Nokomis Beach, Venice Island, the Legacy Trail, Sarasota Memorial Hospital Venice, shopping, dining and I-75—bringing together the Florida lifestyle, resort-style amenities and everyday convenience Toscana Isles is known for.

112 Ventosa Place, Osprey/Nokomis
$1,399,000
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
$165,000
2 Beds ⋅ 2 Baths ⋅ A4706691 MLS
Welcome home to this charming fully furnished 2-bedroom, 2-bath mobile home, built in 2001 and located in the friendly and active Arbors Mobile Home Park in beautiful Osprey, Florida. Featuring an inviting open floor plan, this home offers comfortable living spaces filled with natural light from an abundance of windows. Luxury vinyl plank flooring flows throughout the living areas, creating a clean and cohesive look. The kitchen opens seamlessly to the living and dining areas, making entertaining and everyday living easy. The dining room features a built-in buffet with both lower and upper-glass-front cabinets, providing attractive display space and convenient storage. The primary suite includes a single vanity and walk-in shower, while cathedral ceilings add to the home's open and airy feel. An interior laundry area adds everyday convenience. Outside, a charming shed provides additional storage, and the newer carport, added in 2025, offers covered parking. The AC was replaced in 2024 for added peace of mind. Enjoy the Florida lifestyle in The Arbors, a welcoming 55+ community with a variety of amenities and an active social calendar offering plenty of opportunities to meet neighbors and stay involved. Enjoy the clubhouse, swimming pool, shuffleboard courts and fitness area. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!

23 Siesta Circle W, Osprey/Nokomis
$545,000
3 Beds ⋅ 3 Baths ⋅ N6145611 MLS
"Ahhhhh..." That will be your reaction the moment you step through the front door. Nature-inspired impact glass welcomes you with warmth and natural light, setting the tone for a home that simply feels right. Built in 2019 and impeccably maintained, this stunning 3-bedroom + den, 2.5-bath home offers more than 2,000 square feet of thoughtfully designed living space, along with a large extended lanai overlooking a private backyard, the perfect place to relax, entertain, or simply enjoy Florida living. Just off the foyer, double doors open to a versatile den that can easily serve as a home office, media room, hobby space, or guest retreat. A conveniently located half bath nearby allows visitors easy access without entering the private bedroom areas. Throughout the home, you'll appreciate the serene and cohesive color palette, enhanced by crown molding in every room, chair rail detailing, and plantation shutters, all adding timeless elegance and character. The main living area immediately captures your attention with a striking custom tray ceiling, creating a memorable focal point and adding architectural interest to the space. Designed for gathering, the open-concept kitchen features a gas range, abundant workspace, and a separate butler's pantry that provides additional prep and storage space, making entertaining family and friends effortless. The split-bedroom floor plan offers privacy for everyone. Two generously sized guest bedrooms share a well-appointed guest bath, while the spacious primary suite is tucked away at the rear of the home. Here you'll find a large walk-in shower, dual-sink vanity, private water closet, and an expansive walk-in closet designed to accommodate it all. A roomy laundry room with built-in cabinetry and utility sink adds everyday convenience. For added peace of mind, the home is equipped with accordion-style hurricane protection, offering quick and efficient storm readiness while maintaining excellent curb appeal. Living in Milano is about more than owning a beautiful home, it's embracing a lifestyle. Residents enjoy: No CDD fees, Rental flexibility with two leases a year and a six-month minimum, Gated entry and common area maintenance covered by the HOA, Resort-style community pool, Bocce and pickleball courts, Exclusive resident dog park located just across Jacaranda Boulevard, Active event center with year-round social activities. An added bonus: Milano is located on the same power grid as Sarasota Memorial Hospital and the local fire station, offering an extra layer of confidence when reliable power matters most. This is more than a house. It's a place where comfort, style, community, and peace of mind come together to create a home you'll truly love. Come experience it for yourself.

208 Capriana Court, Osprey/Nokomis
$199,000
2 Beds ⋅ 2 Baths ⋅ C7530710 MLS
Enjoy waterfront Florida living in this updated 2-bedroom, 2-bathroom home with a carport and Florida room in the desirable 55+ community of Terra Cove in Nokomis. Situated at the TIP OF A CANAL, this home offers WATER VIEWS and a peaceful setting to enjoy the Florida lifestyle. Professionally updated in 2024, the interior features LUXURY VINYL FLOORING THROUGHOUT, updated interior paint, and updated light fixtures. INTERIOR FEATURES: • Professionally updated in 2024 • Luxury vinyl flooring throughout • Updated interior paint • Updated light fixtures • Bright and comfortable living spaces • Florida room for additional living and entertaining space • Carport UPDATED KITCHEN: The updated eat-in kitchen combines style and functionality with quartz countertops, a tiled backsplash, and plenty of storage and workspace. A breakfast bar provides additional seating, while the built-in buffet adds convenient storage and serving space. • All white appliances • Quartz countertops • Tiled backsplash • Closet pantry • Built-in buffet with storage • Breakfast bar • Eat-in kitchen PRIMARY SUITE: The spacious primary bedroom offers a comfortable retreat with a walk-in closet and private bathroom. • Walk-in and built-in closets • Private en-suite bathroom • Dual-sink vanity • Walk-in shower GUEST BEDROOM & BATH: The guest bedroom features a walk-in closet and is conveniently located near the guest bathroom. • Walk-in closet • Guest bathroom nearby FLORIDA ROOM & OUTDOOR LIVING: The Florida room expands the home's living and entertaining space, creating a flexible area for relaxing, dining, hobbies, or gathering with guests. Outside, the screened split lanai provides multiple areas to enjoy the surrounding setting, including a front entry patio, workshop, laundry closet, additional seating area, and an outdoor patio overlooking the canal. • Spacious Florida room • Screened split lanai • Front entry patio • Outdoor patio overlooking the water • Workshop • Laundry closet • Additional outdoor seating area • Canal-front location at the tip of the canal • Water views TERRA COVE COMMUNITY & AREA HIGHLIGHTS: Terra Cove is a social 55+ community offering a variety of amenities and opportunities to stay active and connected. Residents can enjoy the community clubhouse, pool, shuffleboard, boat ramp, fishing dock, and watercraft storage. Conveniently located in Nokomis, the community provides easy access to shopping, dining, beaches, boating, and other area amenities. • Active 55+ community • Community clubhouse • Community pool • Shuffleboard • Boat ramp • Fishing dock • Watercraft storage • Waterfront community • Convenient to shopping and dining • Easy access to area beaches • Close to boating, fishing, and outdoor recreation With its WATERFRONT SETTING, WATER VIEWS, 2024 INTERIOR UPDATES, LUXURY VINYL FLOORING, SPACIOUS FLORIDA ROOM, and access to the AMENITIES OF TERRA COVE, this home offers a comfortable opportunity to enjoy the Southwest Florida lifestyle in a welcoming 55+ community.

17 Lafitte Drive, Osprey/Nokomis
$255,000
2 Beds ⋅ 2 Baths ⋅ A4705745 MLS ⋅ 2 BLDG.
TURNKEY Furnished 2 bed, 2 bath two story condo in the lifestyle rich community of Pine Run! Outdoor enthusiasts will love this 20 Acre mature landscaped neighborhood. Nearby, you will find nature parks, walking and biking trails, boat ramps, waterfront dining and minutes to beaches and downtown Venice! Within the community, you can enjoy TWO community pools, pickleball and tennis courts, clubhouse, fitness center and saunas in the community bathrooms. HOA includes Water, Sewer Trash and Pest control. Included with the unit is an assigned outdoor carport space and storage closet. Enjoy the natural lighting and privacy this unit greets you with as you walk through the door. The soaring ceilings bring in natural lighting all day. Updated kitchen with newer, barely used modern appliances and updated cabinetry and countertops. Reverse Osmosis Water softener has been installed to provide the top quality water. On the main floor, you will find a light and bright living room that leads to the oversized screened-in private lanai. Enjoy the wildlife whilst sitting up in the mature trees. The dining area also has a breakfast bar for additional entertaining space. Down the hallway you will find the primary bedroom with two closets, balcony access and entrance to the hallway renovated full bathroom. Also on the main floor is a stackable washer and dryer and large storage closet. Take the serial staircase to the secondary bedroom loft with full bathroom and two closets. The oversized closet is ideal for a walk-in or year round storage. The community is full of life and energy, especially in the winter seasons, and with all of the waterfront dining, parks and attractions nearby, you will always have something to do! Conveniently located near shopping, dining, downtown Venice, Sarasota, major roadways and schools.

109 Woodland Place, Osprey/Nokomis
$645,000
3 Beds ⋅ 2 Baths ⋅ A4704539 MLS
Virtually Staged. One or more Photos have been virtually staged. Welcome to 5548 Sentiero Drive, a beautifully maintained Taylor Morrison-built, 3-bedroom, 2-bath home with a den and 1,944 square feet of living space, located in the gated Bellacina by Casey Key community in Nokomis, Florida. Designed for comfortable Florida living, this inviting home offers an open floor plan, high ceilings, abundant natural light, and thoughtfully designed indoor and outdoor spaces. The spacious living area features an elegant tray ceiling and flows seamlessly into the kitchen and dining areas, creating an open and welcoming space for everyday living and entertaining. The kitchen features granite countertops, stainless steel appliances, a gas cooktop, custom cabinetry, and a large center island, with an adjacent dining area. The private primary suite offers a spacious bedroom with a tray ceiling, walk-in closet, dual vanities, and a glass-enclosed shower. Two additional bedrooms provide comfortable space for family or guests, while the separate den offers flexibility as a home office, media room, reading room, or hobby space. A dedicated laundry room with cabinetry and an attached two-car garage provide additional storage and convenience. Step outside to the covered, screened lanai and beautifully landscaped backyard, an inviting setting for morning coffee, outdoor dining, or simply enjoying Florida's year-round sunshine. Bellacina by Casey Key offers a low-maintenance, resort-style lifestyle with a clubhouse, fitness center, heated resort-style pool and spa, pickleball and tennis courts, bocce ball, dog park, fire pit, walking trails, kayak launch, and community activities. Lawn maintenance is included, giving you more time to enjoy the Gulf Coast. NO CDD fees add to the appeal. And when location matters, this one is hard to beat—Nokomis Beach and the Gulf of Mexico are less than 10 minutes away, with Casey Key, the Legacy Trail, Oscar Scherer State Park, Downtown Venice, shopping, dining, golf, and Sarasota Memorial Hospital – Venice all nearby. Sarasota is also just a short drive north. Whether you're looking for a full-time residence, seasonal Florida home, or low-maintenance Gulf Coast retreat, 5548 Sentiero Drive offers an outstanding combination of location, lifestyle, and community amenities. Schedule your private showing today!

5548 Sentiero Drive, Osprey/Nokomis
$529,000
4 Beds ⋅ 2 Baths ⋅ A4704589 MLS
Priced to sell! Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble backsplash, recessed lighting, an undermount sink, and newer Whirlpool appliances. A split floor plan provides privacy with spacious bedrooms, including a primary suite with lanai access, two closets (one walk-in), and a spa-like bath with soaking tub, walk-in shower, and dual quartz vanities. The screened lanai overlooks an inviting pool and spa with a private, tree-lined backdrop. Other highlights include a dedicated laundry room, 2-car garage with new door and opener, newer roof, A/C, and water heater. All improvements and system updates completed in 2020. Last year, the pool was resurfaced and the waterline tile replaced. Additional upgrades include new pool equipment, a saltwater system, and a heater. Low HOA and no CDD. Conveniently located near top-rated schools, Oscar Scherer State Park, shopping, dining, and world-class beaches including Siesta Key, Nokomis, and Venice.

583 Pine Ranch East Road, Osprey/Nokomis
$1,495,000
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
Start Your Search