Osprey Homes with Pool View

Osprey Homes with Pool View

Welcome to Osprey, Florida, a hidden gem nestled in the heart of Sarasota County. This charming community seamlessly blends the tranquility of coastal living with the vibrancy of nearby urban amenities. Known for its stunning natural beauty, Osprey boasts picturesque views of the Gulf of Mexico, lush landscapes, and a wealth of outdoor recreational opportunities. Whether you're strolling along the pristine beaches or exploring the serene waters of the nearby intercoastal, Osprey offers a lifestyle that's both relaxing and invigorating.

One of the most appealing aspects of this delightful region is the availability of homes with captivating pool views. Imagine waking up each morning to the gentle shimmer of water reflecting the sun's rays, or unwinding in your private oasis as you soak in the warm Florida sunshine. Homes in Osprey with pool views provide the perfect backdrop for entertaining friends and family or simply enjoying a quiet evening under the stars. With an array of architectural styles, from charming bungalows to elegant estates, you’re sure to find a residence that perfectly suits your taste and lifestyle.

In addition to its stunning homes, Osprey is conveniently located near a variety of shopping, dining, and cultural experiences. Enjoy fresh seafood at local eateries, explore art galleries, or take a short drive to the vibrant city of Sarasota, known for its rich arts scene and beautiful botanical gardens.

Discover the enchanting lifestyle that awaits you in Osprey, where every day feels like a vacation, and your dream home with a pool view is just around the corner!

Newest Osprey Homes with Pool View

$799,000
4 Beds ⋅ 3 Baths ⋅ Park Trace Estates SubDv. ⋅ 34229 Zip Code
MODERN COASTAL MASTERPIECE | OVER $200,000 IN LUXURY UPGRADES | NEW ROOF | HEATED SALTWATER POOL | PINE VIEW SCHOOL DISTRICT Welcome to one of Park Trace Estates’ finest fully renovated homes, where sophisticated design, exceptional craftsmanship, and the Florida lifestyle come together in perfect harmony. This spectacular 4-bedroom, 3-bath residence has been extensively remodeled with over $200,000 in premium upgrades, creating a truly move-in-ready luxury retreat. From the moment you arrive, you’ll be captivated by the home’s outstanding curb appeal, featuring professionally designed tropical landscaping, an elegant paver walkway, and a welcoming entrance that immediately sets the tone for what’s inside. Step through the front door into a breathtaking open-concept floor plan showcasing soaring ceilings with custom decorative beams, an impressive floor-to-ceiling designer stone fireplace, abundant natural light, and exquisite designer finishes throughout. Every detail has been carefully selected to create a warm, elegant, and timeless coastal living experience. The heart of the home is the stunning chef’s kitchen, completely redesigned with premium finishes, featuring Bosch stainless steel appliances, oversized quartz countertops, custom cabinetry, and an expansive island perfect for entertaining family and friends. The spacious split-bedroom floor plan offers privacy and comfort, while three beautifully remodeled designer bathrooms provide a spa-like experience with luxury finishes and exceptional attention to detail.Expansive sliding glass doors seamlessly blend indoor and outdoor living, opening to your own private resort-style courtyard featuring a heated saltwater pool and spa, creating the perfect setting for entertaining or simply enjoying Florida’s year-round sunshine. Extensive Premium Improvements Include: ? NEW $60,000 Tile Roof ? NEW High-Efficiency HVAC System (2024) ? Completely Remodeled Designer Kitchen ? Premium Bosch Stainless Steel Appliances ? Oversized Quartz Countertops & Custom Cabinetry ? NEW Luxury Vinyl Flooring Throughout ? Three Fully Remodeled Designer Bathrooms ? Custom Floor-to-Ceiling Stone Fireplace ? Decorative Custom Ceiling Beams ? Freshly Painted Interior Throughout ? Freshly Painted Exterior ? Professionally Designed Custom Accent Walls with Premium Designer Finishes ? NEWER Saltwater Pool System ? NEW Pool Heater ? Aqua Whole-House Water Filtration System ? Water Softener ? NEW Water Heater ? NEW Vinyl Privacy Fence v Custom-designed green wall at the patio and at the entrance. ? Professionally Designed Tropical Landscaping (Approx. $20,000) ? Over $200,000 Invested in Quality Renovations & Improvements Located in the highly desirable Park Trace Estates, this exceptional property is just minutes from world-famous Siesta Key Beach, Nokomis Beach, the award-winning Pine View School, Legacy Trail, shopping, healthcare, and the natural beauty of Oscar Scherer State Park, offering kayaking, hiking, biking, and endless outdoor recreation. Situated in Flood Zone X with low HOA fees of approximately $55/month, this meticulously upgraded residence offers peace of mind, luxury, and an unbeatable location. This is more than a home—it’s a lifestyle. Every room reflects quality, craftsmanship, and thoughtful design. With over $200,000 invested in premium upgrades, this exceptional property is truly one of the finest opportunities currently available in Park Trace Estates.

Osprey
$1,790,000
3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.

206 Four Knot Lane, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.

156 Bishops Court Road, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey
$899,995
3 Beds ⋅ 3 Baths ⋅ Villas At Osprey Harbor Village SubDv. ⋅ 34229 Zip Code
Enjoy breathtaking sunset views overlooking the intercostal waterway in this boater's paradise, complete with an on-site marina. Discover coastal living in this beautifully updated 3-bedroom, 2.5-bath residence located in Bellagio Harbor Village. Ideally positioned between Sarasota Big Pass and the Venice Jetty, and just minutes from Midnight Pass and the Gulf of Mexico, this home offers easy access to pristine beaches, fine dining, and boutique shopping. Walkable to local restaurants and boat docks, the community is both conveniently located and peacefully serene. Offering 2,199 square feet of thoughtfully designed living space, this residence has been enhanced for comfort and style. Updates include new lighting throughout, featuring four coastal ceiling fans and elegant Caprice chandeliers. The spacious primary suite and two additional bedrooms feature new cordless blinds and window treatments, creating private and tranquil retreats. Bathrooms have been refreshed with new toilets, fresh paint, and an updated vanity in the powder room. The well-appointed kitchen showcases shaker-style cabinetry and enjoys stunning Intracoastal and sunset views. Step onto the private lanai and enjoy seamless indoor-outdoor living with direct access to the pool area. Newly installed retractable screens provide shade and privacy when desired while preserving expansive water views. Outdoor enthusiasts will appreciate the on-site kayak storage and launch area, perfect for exploring the surrounding waterways. Located in southwest Osprey, this exceptional residence offers both a beautiful home and a vibrant waterfront community. Residents enjoy access to a resort-style pool, hot tub, sauna, and open-concept gathering spaces—creating a lifestyle where every day feels like a vacation.

14021 Bellagio Way Unit 309, Osprey
$1,095,000
4 Beds ⋅ 3 Baths ⋅ Pine Ranch SubDv. ⋅ 34229 Zip Code
Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.

403 Longbow Trail, Osprey
$1,950,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE BEDROOMS, 5.5 BATHS, and a 3-CAR GARAGE that’s been freshly painted and upgraded with a new epoxy floor. Walls of glass fill the home with natural light, complemented by plantation shutters and new motorized window shades throughout. Major updates include a new tile roof (August 2025), two new HVAC units, new LED lighting, and new outlets and light switches across the home. The entire interior and exterior were freshly painted in 2023, giving the home a bright and modern aesthetic. The primary suite is a private retreat, featuring new flooring, a spacious bath, and a bonus office/dressing area for added versatility. A separate office or sitting room, also with new floors, provides ideal space for remote work or quiet relaxation. The three additional bedrooms feature new carpeting, creating a cohesive and comfortable atmosphere. The chef’s kitchen is equipped with new stainless-steel appliances (refrigerator, dishwasher, – all 2025) and flows seamlessly to the main living areas and outdoor entertainment space. There is a new 2025 washer and dryer as well. Step outside to your private Florida oasis — a covered lanai with a full outdoor kitchen and a large motorized Sunbrella shade for comfort and convenience. The property’s two fountains (one new) and professionally graded, elevated landscaping create a lush and tranquil environment perfect for al fresco dining or quiet reflection. 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**

538 Dove Pointe Drive, Osprey
$1,595,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

909 Macewen Drive, Osprey
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