Osprey/Nokomis Homes with Buyer Approval Required Community Features

Osprey/Nokomis Homes with Buyer Approval Required Community Features

Welcome to the charming coastal communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These picturesque towns are renowned for their stunning natural beauty, vibrant culture, and a welcoming atmosphere that makes them ideal for families, retirees, and everyone in between.

Osprey, with its rich history and lush landscapes, offers residents a serene lifestyle that’s just a stone's throw from the sparkling Gulf of Mexico. Enjoy leisurely strolls along the scenic trails of Oscar Scherer State Park or indulge in the local dining scene, which boasts an array of delightful eateries. Just a short drive away, Nokomis enchants with its pristine beaches, quaint shops, and a laid-back vibe that captures the essence of Florida living.

For those looking to invest in this idyllic region, homes in Osprey and Nokomis often come with unique community features that add to their appeal. Many neighborhoods require buyer approval, ensuring that residents share a commitment to maintaining the integrity and charm of the community. This thoughtful approach fosters a close-knit environment where neighbors become friends, and families can thrive together.

Whether you’re seeking a cozy bungalow near the beach or a spacious family home with room to grow, the real estate options in Osprey and Nokomis are diverse and inviting. Embrace the opportunity to live in a place where sun-kissed days and vibrant sunsets are part of your everyday life. Discover the magic of Osprey and Nokomis, and let your dream home become a reality in this enchanting slice of Florida paradise.

Newest Osprey/Nokomis Homes with Buyer Approval Required Community Features

$629,400
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
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
$450,000
3 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
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, Nokomis
$1,399,000
3 Beds ⋅ 3 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code
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
$165,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
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
$545,000
3 Beds ⋅ 3 Baths ⋅ Milano Ph 2 Rep 1 SubDv. ⋅ 34275 Zip Code
"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, Nokomis
$199,000
2 Beds ⋅ 2 Baths ⋅ Terra Cove SubDv. ⋅ 34275 Zip Code
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, Nokomis
$255,000
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
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
$645,000
3 Beds ⋅ 2 Baths ⋅ Bellacina By Casey Key SubDv. ⋅ 34275 Zip Code
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, Nokomis
$529,000
4 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34229 Zip Code
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
$1,495,000
3 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
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
$540,000
3 Beds ⋅ 3 Baths ⋅ Blackburn Point Marina Village SubDv. ⋅ 34229 Zip Code
Virtually Staged. Welcome to Blackburn Point Marina Village, an intimate gated waterfront community of just 19 residences near Sarasota and Casey Key. This beautifully upgraded townhome delivers a relaxed coastal lifestyle with low-maintenance living—without the waterfront price tag. A bright, open floor plan features 9-foot ceilings, plantation shutters, ceiling fans, and new luxury vinyl flooring installed in 2025. The enclosed sunroom adds versatile living space for relaxing, entertaining, or enjoying the Florida sunshine. The gourmet kitchen is designed for both everyday living and entertaining, with granite countertops, Craft Maid cabinetry, a KitchenAid gas range, LG refrigerator (2023), and wine refrigerator. Enjoy peace of mind with a new roof (2025), water filtration and softener system (2024), tankless water heater, motorized hurricane shutters, epoxy-finished garage floor, and a LiftMaster garage door with camera (2025). The first-floor primary suite provides a private retreat, complete with dual vanities, a soaking tub, and a walk-in shower. Ideally located near Casey Key Marina, Blackburn Point Park, and Casey Key Fish House & Tiki Bar, this home puts boating, waterfront dining, and outdoor recreation close at hand. Community amenities and water and gas service are included, making this an exceptional opportunity to enjoy the Sarasota coastal lifestyle. One or more photo(s) was virtually staged.

1140 Beachcomber Court Unit 11, Osprey
$225,000
2 Beds ⋅ 2 Baths ⋅ Kings Gate Club SubDv. ⋅ 34275 Zip Code
Welcome to easy Florida living in desirable Kings Gate Park! This newer, move-in-ready home offers a bright, open-concept layout designed for comfortable everyday living and effortless entertaining. Thoughtful upgrades add even more value, including a whole-home backup generator for added peace of mind, a private mobility lift for convenient accessibility, and exterior sunshades to help keep your Florida lifestyle cool and comfortable. With its fresh feel and low-maintenance design, this home is ready for you to simply unpack and start enjoying! Kings Gate Park is a sought-after 55+ community where residents enjoy individually owned lots, low HOA fees, and an active, amenity-filled lifestyle. Spend your days at the community pool, playing tennis, pickleball or shuffleboard, or take advantage of the community boat ramp with direct access to the Intracoastal Waterway for boating and fishing adventures. An active social calendar offers plenty of opportunities to meet neighbors and enjoy the community. Ideally located just minutes from Gulf beaches, golf courses, medical facilities, shopping, dining, and the many cultural attractions of Venice and Sarasota. All furnishings are negotiable, making this an exceptional opportunity for buyers looking for a move-in-ready primary residence, seasonal retreat, or turnkey second home. If you've been dreaming of sunshine, sunsets, time on the water, and a relaxed Southwest Florida lifestyle, this home is ready to welcome you!

44 Crown Point Drive, Nokomis
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