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

$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
$985,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
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
$399,000
3 Beds ⋅ 2 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code
Welcome home to Toscana Isles, where this beautifully maintained 3-bedroom, 2-bath Clifton floor plan offers the ease of single-story living paired with one of Nokomis’ most sought-after resort-style communities. Designed with an open, easy flow, the kitchen overlooks the spacious great room and dining area, creating a natural gathering space for everyday living and entertaining. The well-appointed kitchen features a large island, stainless steel appliances, generous cabinet and counter space, and a walk-in corner pantry. Just beyond the main living area, sliding doors open to the covered and private pavered lanai, extending the living space outdoors and offering the perfect place for morning coffee, evening cocktails, or simply enjoying the Florida weather. The primary suite is privately positioned at the back of the home and features two generous walk-in closets and an ensuite bath with dual vanities and a glass-enclosed shower. Two additional bedrooms are located toward the front of the home, creating comfortable separation for family or guests, with the flexibility to use one as a home office when needed. Living in Toscana Isles is about more than the home. At the center of the community is an impressive 8,000-square-foot clubhouse overlooking the water, with an infinity-edge heated pool, fitness center, clubroom, tennis, pickleball, bocce, dog park, and scenic walking areas. Residents can also enjoy kayaking, canoeing, and fishing throughout 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. Whether you’re looking for a full-time residence or an easy Florida retreat, this home puts the Gulf Coast lifestyle right at your doorstep.

308 Soliera Street, Nokomis
$599,000
2 Beds ⋅ 3 Baths ⋅ The Harbor Villas At Dona Bay SubDv. ⋅ 34275 Zip Code
Live the SALT LIFE! This unit is a BOATER'S DREAM! Enjoy breathtaking waterfront living in this beautifully updated 2-bedroom, 2.5-bath condo overlooking Dona Bay with direct access to the Intracoastal Waterway and Gulf of Mexico. This spacious 1,642 sq. ft. residence is sunny and bright, features an open floor plan with high ceilings, solid wood cabinetry, solid-surface countertops, and beautiful water views from the kitchen, living, dining areas, and expansive covered front porch. Step outside and enjoy your private waterfront lifestyle with a deeded dock and recently installed 10,000-lb. boat lift, providing convenient access to the Gulf with no bridges and approximately 5 minutes by boat to Venice Inlet. The unit also includes two deeded parking spaces in the enclosed first-floor garage, with private elevator access directly to the residence. Located in The Harbor Villas at Dona Bay, residents enjoy a waterfront community with a pool, fitness center, sidewalks, and water access. Conveniently located along Tamiami Trail in Nokomis, close to Venice, beaches, dining, shopping, and outdoor recreation. A rare opportunity to own a waterfront retreat designed for enjoying the Florida boating lifestyle!

516 Tamiami Trail S Unit 306, Nokomis
$719,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
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
$775,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Semi-furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic intracoastal water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy breathtaking sunsets from your private screened-in balcony as you look out across the bay to the barrier island of Casey Key. Inside the unit, you'll find a spacious living room and dining room featuring an open floor plan. The gourmet kitchen offers KitchenAid stainless steel appliances, quartz countertops, white shaker-style cabinetry, counter seating and plenty of storage cabinets. The primary bedroom is expansive with large walk-in closets, closet organization system and direct access to the outside balcony. Both guest bedrooms have dual purpose, as they both have built-in Murphy beds, desk workstations, plantation shutters and walk-in closets. If you're looking for a condominium with extra space for a den/office/sewing room/craft room or TV media room, this is the one that offers it all. More great features are impact-resistant windows and doors, a large laundry room with built-in cabinetry, a full-size washer and dryer and utility sink. One assigned parking space with a large storage unit with a roll-down door for all your extra gear. Some of the amenities include a new fishing pier, lit pickleball courts, kayaking and kayake racks for storage, clubhouse, swimming pool, spa and tiki hut with grilling barbeque stations. The location is walkable to many restaurants, shopping and the post office. Bike the Legacy Trail or head to the beach that's just a few miles away. There's so much to do just minutes away.

260 Hidden Bay Drive Unit 402, Osprey
$698,713
3 Beds ⋅ 3 Baths ⋅ Venetian Golf & River Club SubDv. ⋅ 34275 Zip Code
The Da Forli Model, built by WCI, with expansive, serene GOLF COURSE, LAKE and PRIVATE PRESERVE Views. A covered Loggia entry to light filled foyer with views of the great room. Sliders lead you out to the large screened lanai with heated pool and spa overlooking the Golf Course, Lake and Private Preserve Views! The home has many upgrades including: custom tile flooring, lots of natural lighting, soaring and custom tray ceilings, 2 zone A/C 16 seer(THAT HS BEEN UNDER A SERVICE AGREEMENT EVERY 6 MONTHS. JSUT SERVICE AND IS TRANSFERRABLE), central vac system, surround sound system, custom architectural arches, a 2 CAR GARAGE PLUS GOLF CART PARKING! 3 Bedrooms, 3 full baths plus a Den/Office, BEING SOLD PARTIALLY FURNISHED BUT JUST ABOUT TURN KEY ! The kitchen is a dream for the chef or host as it open to the family room, a cafe style dining area with access for pool side entertaining. Stainless steel appliances, a gas range, breakfast bar, lots of cabinetry and stunning granite counters; just a few steps to the great room and formal dining room. For owners you have a large suite with soothing views, tray ceilings, his and her closets, a luxurious bath with both a garden tub and walk in shower, dual sinks and a private water closet. 2 guest suites, stunningly appointed to create a warm cozy environment, feature a jack and jill bath making it very convenient. Your guests and family will have plenty of space with the family room and the great room both with golf course, lake and calming preserve views. You will find a double door entry to the office/den/study or 4th bedroom (desk insert area can be converted to closet) and just outside its doors a private bath. The oversized two car garage has room for 2 cars and your golf cart! The home was constructed with hurricane hardening features including impact resistant rated windows and full shutter coverage on lanai. Venetian and Golf and River Club is a gated community with many fine amenities including an 18-hole championship golf course, large, heated pool and lap pool, six Har-Tru tennis courts, a nature trail, first class fitness center and exercise room with classes. The River Club also boasts a poolside Tiki Bar and fine dining in its restaurant. About 3 miles to Venice beaches , attractions of downtown Venice and the reassurance of the services offered by the newly completed renowned Sarasota Memorial Hospital. Previous inspection revealed a few items of needed repair and or replacement, heirs willing to negotiate repairs with acceptable offer.

194 Montelluna Drive, North Venice
$1,900,000
5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey
Start Your Search