Location: Osprey
Do Not Show Listings
759 FORDINGBRIDGE WAY, OSPREY, FL 34229
$749,00069 Days on yellowkey MLS ID: O6399774
REDUCED by $21,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 2002Monthly Fee: $55 Tax: $7,129 (2025)Community: Rivendell WoodlandsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,129
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1367 THORNAPPLE DR, OSPREY, FL 34229
$579,00021 Days on yellowkey MLS ID: A4695210
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2182 Built: 2003Monthly Fee: $397 Tax: $5,745 (2025)Community: Willowbend Ph 1Spa: NoSingle Family
Taxes:$5,745
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: Discover unparalleled luxury in this exquisite Lee Wetherington-built residence, ideally in Willowbend within Osprey. A grand entry hall with high-end finishes, tray ceilings and rich crown molding welcomes you to a home meticulously perfected by discerning sellers. This ideally positioned home boasts a ¼+ acre homesite with an expansive front yard, a roomy side-entry paver newly sealed driveway and an oversized garage, recently painted. Enjoy private outdoor living on the lanai and in the backyard, enhanced by mature landscaping for ultimate privacy and shade. Go inside to a stunning retreat featuring 20-inch porcelain tile throughout the entire residence, marble inlays, wide crown molding, elegant arches and plantation shutters, all within the popular Willow floor plan. An inviting gathering and dining room lead to the heart of the home, including an amazing gourmet kitchen with new stainless appliances and natural gas cooking, granite counters and trending painted cabinets. A separate breakfast nook offers tranquil views, while the family room, with its tray ceiling and triple sliders, opens to an outdoor haven. The spacious owner’s suite is a sanctuary, complete with walk-in closets, dual granite sinks, a walk-in shower, a deep garden tub and lanai access. Two additional bedrooms share a bath, and a lovely den/office features bay windows. Hurricane protection on all doors and windows installed in 2021 for peace of mind. Low HOA fees cover yard maintenance, irrigation, high-speed internet, streaming cable, a heated community pool/spa, fitness center, basketball, pickleball and playground. Location is everything! Enjoy proximity to beautiful Gulf beaches, Oscar Scherer State Park, Legacy Bicycle Trail, Pine View School, waterfront restaurants, tiki bars, Publix and new Foxtail Coffee. Experience the art of living in this extraordinary home with exceptional curb appeal and lush landscaping.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
742 HARMS DR, OSPREY, FL 34229
$515,000267 Days on yellowkey MLS ID: A4666421
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1293 Built: 1981 Tax: $5,620 (2024)Community: Harms SubSpa: NoSingle Family
Taxes:$5,620
Tax Year: 2024
Remarks: Beautifully renovated and move-in ready, this exceptional property offers the perfect blend of privacy, comfort, and investment potential. Situated on over half an acre along a private, tree-lined street, the home is surrounded by lush tropical landscaping, creating a peaceful oasis just minutes from everything Sarasota has to offer. Step inside to discover a spacious, thoughtfully updated interior featuring modern finishes and an effortless flow between indoor and outdoor living spaces. The heated pool and expansive screened lanai provide the perfect setting for relaxing, entertaining, and enjoying Florida’s year-round sunshine. This turnkey home has been meticulously maintained and boasts a proven track record as a successful income-producing rental. Major upgrades offer peace of mind, including a complete interior renovation, new roof, and pool cage rescreening (2021), pool pump (2022), HVAC system (2023), and a new water heater, well pump, and garage door opener (2024). Additional recent improvements include an automated pool cleaner and septic system flush (2025). Perfectly positioned between Sarasota and Venice, you’ll enjoy easy access to world-class beaches, waterfront dining, shopping, and entertainment. Nature lovers will appreciate having Oscar Scherer State Park directly across the street, offering scenic trails, kayaking, and renowned birdwatching, while the Osprey Junction Trailhead provides quick access to the Legacy Trail just minutes away for biking, walking, and outdoor recreation. With NO HOA restrictions and ample room for a boat, RV, or other recreational vehicles, this property offers a rare combination of flexibility and freedom. Whether you’re seeking a full-time residence, seasonal retreat, or income-producing investment, this beautifully updated home delivers the Florida lifestyle you’ve been looking for.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Tiffany Stonis (941-204-5239)
127 PARK TRACE BLVD, OSPREY, FL 34229
$795,00051 Days on yellowkey MLS ID: A4692408
1 Days Off yellowkey (back on 5/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2463 Built: 2003 Tax: $4,379 (2025)Community: Park Trace EstatesSpa: YesSingle Family
Taxes:$4,379
Remarks: Under contract-accepting backup offers. Flawless from top to bottom, this beautifully maintained Florida home offers over 3,000 sq. feet of indoor and outdoor living space, perfect for casual or elegant entertaining. With more than $175,000 in recent upgrades, this stunning water view property blends luxury with peace of mind. Highlights include a new roof, a refinished pool and spa with new heater, and built in Char Broil grill for the ultimate backyard escape. Lush tropical landscaping surrounds the front and back, adding year-round beauty and privacy. Inside, you will find a renovated gourmet kitchen, wood cabinetry, sleek porcelain tile floors, double tray ceilings, and remote-controlled Hunter Douglas blinds. The primary suite is a private getaway with a luxury spa style bath and custom bespoke closet, while six rooms boast gorgeous water views and natural light. In addition you will find an oversized garage with additional overhead storage and built-in work bench Located in the coveted Park Trace Estates in Osprey, you're just 6.5 miles from Siesta Key Beach, a short walk to the Legacy Trail, and jump on a kayak near-by at Oscar Scherer State Park. Adding even more appeal, it is also a short walk to the nationally acclaimed Pine View School. This move-in ready luxury home blends lifestyle, location, and exceptional quality in a beautiful community with HOA's of only $58 a month!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kim Azar-Calka (239-216-6205)
101 OSPREY POINT DR, OSPREY, FL 34229
$4,790,00029 Days on yellowkey MLS ID: A4694716
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5087 Built: 1985Monthly Fee: $950 Tax: $12,940 (2025)Community: The OaksSpa: YesSingle Family
Taxes:$12,940
Middle School: Sarasota Middle
Remarks: Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
18 N CASEY KEY RD, OSPREY, FL 34229
$1,750,000247 Days on yellowkey MLS ID: A4669083
0 Days Off yellowkey (back on 6/1/2026)
REDUCED by $250,000 (12.5%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1977 Built: 1973 Tax: $24,015 (2024)Community: Casey KeySingle Family
Taxes:$24,015
Remarks: Under contract-accepting backup offers. Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal for quiet retreats, reading or working from home. Enjoy serene views of the bay and Intracoastal Waterway from the primary suite, a coastal sanctuary. Set on over half an acre, the expansive backyard features a large screened-in pool and lush landscaping, creating your own private tropical paradise by the water. The deeded easement directly across the street leads to a secluded sandy beach, offering endless days of sun, sea, and tranquility. The property remained unaffected by recent storms, a testament to its solid construction and meticulous upkeep. Recent upgrades include mew metal roofs on the home and garage (2020), HVAC system replacement (2020), new water heater (2021), PGT impact-rated windows and doors (2012) and new garage door (2012). Ideally situated for easy access on and off the key, this residence is also close to top-tier shopping, dining, golf, tennis and recreational amenities. With Sarasota and Venice just a short drive away, you’ll enjoy a balance of island living and urban convenience.
Listing Agent: Valerie Dall'Acqua (941-445-7295)
352 GLENWOOD AVE, OSPREY, FL 34229
$417,000400 Days on yellowkey MLS ID: N6138982
REDUCED by $12,500 (2.9%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1300 Built: 2021 Tax: $4,355 (2024)Community: Siesta Rev Resub Of PtSingle Family
Taxes:$4,355
Remarks: Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel. With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational vehicles with ease. The generous lot offers plenty of room for parking and outdoor enjoyment. Don’t miss this rare opportunity to own a centrally located, low-maintenance home in a highly desirable area!
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-923-5835)
Listing Agent: Kano Keller (941-915-1297)
212 WASHINGTON AVE, OSPREY, FL 34229
$427,00052 Days on yellowkey MLS ID: O6404307
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1478 Built: 1999 Tax: $3,294 (2025)Community: Ogburns T B AddSpa: NoSingle Family
Taxes:$3,294
Remarks: One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey— perfectly situated on a premium corner lot with NO HOA and NO CDD fees! This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious living area features sliding glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating seamless indoor-outdoor living. The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk- in closet, providing ample storage and convenience. Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing off after a swim. Additional highlights include a two-car garage, functional layout, and a yard that offers both privacy and potential. With its corner lot location and private pool this home delivers the ultimate Florida lifestyle. Opportunities like this don’t last—schedule your private showing today and make this Osprey gem yours!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jeff Jones (205-902-3584)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000263 Days on yellowkey MLS ID: A4667263
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4096 Built: 1969Monthly Fee: $33 Tax: $37,172 (2024)Community: Casey KeySpa: NoSingle Family
Taxes:$37,172
Remarks: Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.
Listing Agent: Lisa Napolitano (941-993-0025)
293 TURQUOISE LN, OSPREY, FL 34229
$875,000530 Days on yellowkey MLS ID: A4633961
REDUCED by $35,000 (3.8%) on 05/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2271 Built: 2001Monthly Fee: $400 Tax: $7,520 (2024)Community: OaksSpa: NoSingle Family
Taxes:$7,520
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. 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.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
4429 CONCHFISH LN, OSPREY, FL 34229
$535,00054 Days on yellowkey MLS ID: A4689967
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2004 Built: 2018Monthly Fee: $147 Tax: $5,968 (2025)Community: Palms/Casey KeySingle Family
Taxes:$5,968
Remarks: Beautiful residence located in The Palms of Casey Key community, offering a thoughtfully designed layout ideal for everyday living and entertaining. The home spans approximately 2,000+ square feet and features updated flooring throughout all bedrooms and closets, along with tile in the main living areas for durability and easy upkeep. A spacious great room anchors the interior, creating a natural gathering space for family and guests, while the private primary suite is set apart at the rear of the home and includes dual sinks, a soaking tub, walk-in shower, and generous closet space. Outdoor living is highlighted by a covered lanai overlooking a private backyard, ideal for relaxing or entertaining. Additional features include a two-car garage and a well-maintained neighborhood setting with HOA oversight and community amenities nearby. Positioned just steps from Pine View School, it also provides convenient access to US-41 and I-75, placing top-rated schools, beaches, marinas, dining, and shopping just minutes away.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)
Listing Agent: Jennifer Kenna (941-253-3003)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$875,000124 Days on yellowkey MLS ID: A4681662
0 Days Off yellowkey (back on 5/24/2026)
REDUCED by $12,000 (1.4%) on 05/14/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2870 Built: 2003Monthly Fee: $437 Tax: $5,460 (2025)Community: Willowbend Ph 2Spa: YesSingle Family
Taxes:$5,460
Remarks: It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features unobstructed shimmering views of a wide lake and the natural beauty of the park, creating an extraordinary backdrop for an exceptional lifestyle. The idyllic setting includes a sparkling heated pool and spa. Summer kitchen has sink and stainless beverage refrigerator with large bar entertaining area. The exterior boasts a three-car garage and a double-door that welcomes you into an inviting, spacious interior. The home’s open floor plan includes living/dining with views to the natural beauty, tile on diagonal, crown molding and vaulted ceilings. Handsome office/den to the front of residence. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, including built-in gas range and custom hood. Large walk-in pantry with oversized adjacent laundry room that has an additional deep closet. Dinette area features an aquarium window to take in the natural beauty. Family room is spacious with a corner pocket door that opens wide to let in Florida’s finest weather. The primary suite offers bamboo wood floors, double-tray ceiling and sitting area with French doors. California-style walk-in closets and a luxurious bath with dual sinks, a tub, walk-in shower and separate toilet. Each guest bedroom is generous in size with full bath in between. Additionally, it is a bonus living space with wood floors overlooking the serene setting. Third bath serves as pool bath. On a practical note, new water heater in 2026 and pool pump in December 2025. An amazing lifestyle awaits, all overlooking serene waterfront views teeming with wildlife such as eagles, osprey, otters, turtles and deer. The home is ideally near downtown Venice, Sarasota, Siesta Key, Nokomis Beach and Legacy Trail, offering easy access to cultural attractions, shopping, dining and recreational activities. Short distance to nationally ranked Pine View School. The community’s low fees include internet, Direct TV streaming, yard maintenance, irrigation, pool and spa, gym and pickleball, making this a harmony of luxury, comfort and stunning beauty.
103 BISHOPS COURT RD, OSPREY, FL 34229
$749,00033 Days on yellowkey MLS ID: A4694468
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2034 Built: 2000Monthly Fee: $425 Tax: $3,743 (2025)Community: OaksSpa: NoSingle Family
Taxes:$3,743
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. 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.
13 BAYHEAD LN, OSPREY, FL 34229
$799,000447 Days on yellowkey MLS ID: A4645829
REDUCED by $51,000 (6.0%) on 05/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2310 Built: 2001Monthly Fee: $425 Tax: $3,620 (2024)Community: OaksSpa: NoSingle Family
Taxes:$3,620
Remarks: **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. 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**
49 OSPREY POINT DR, OSPREY, FL 34229
$2,399,000223 Days on yellowkey MLS ID: A4671762
REDUCED by $101,000 (4.0%) on 05/03/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3953 Built: 1989Monthly Fee: $475 Tax: $14,206 (2024)Community: OaksSpa: YesSingle Family
Taxes:$14,206
Remarks: Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Jonathan Abrams, Pllc (941-232-2868)
524 SARABAY RD, OSPREY, FL 34229
$419,000180 Days on yellowkey MLS ID: A4676179
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1760 Built: 1956 Tax: $1,926 (2025)Community: Bay Acres - ResubSingle Family
Taxes:$1,926
Remarks: Location, Location. In the Heart of Osprey, centrally located in the highly sought-after well-established Bay Acres Community. Lowest priced home west of the Taril. These 3 bedrooms 2 bath ranch home is West of 41 within 10-minute commutes to downtown Sarasota and downtown Venice, Florida. Across the street from Walmart with bus transportation to Sarasota and Venice. You can walk to Walmart, the post office and two Tiki bars. You can launch your kayak from the private waterfront park on a protected bay with dockage for boats up to 22 feet. There is a waiting list for the dockage. Bay Acres is a non-deed-restricted neighborhood. You can park your RV or commercial vehicles on your property. Major updates include new roof, 3 years old, exterior paint 3 years, New HVAC this year, a Water treatment system recently installed and a rescreened lanai. Some interior updates have been done, but most need personal touches. This house has a new neighbor owned fence at the back of the lot and no fence at either side. The lot is large enough for a pool.
Listing is courtesy of: SUN N SAND REAL ESTATE LLC (574-252-6049)
Listing Agent: Ibett Giannone (574-252-6049)
272 FOUR KNOT LN, OSPREY, FL 34229
$1,095,00042 Days on yellowkey MLS ID: N6144313
1 Days Off yellowkey (back on 5/16/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2723 Built: 1978Monthly Fee: $219 Tax: $5,738 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$5,738
Remarks: Under contract-accepting backup offers. Welcome to this simply stunning, meticulously maintained 5-bedroom, 3-bath residence located in the highly sought-after Southbay Yacht & Racquet Club. Proudly offered by the original owner, this exceptional home showcases true pride of ownership throughout. Situated on a beautifully treed and lushly landscaped lot, the property offers privacy, elegance, and outstanding outdoor living. The sparkling inground pool and brand-new 2025 pool cage create the perfect setting for entertaining or relaxing in your own tropical retreat. The expansive lanai features gorgeous 24x24 pavers and enhanced outdoor electrical lighting for unforgettable evenings outdoors. Inside, the home has been thoughtfully updated with a beautifully renovated kitchen with custom tile work, double ovens, quartz countertops. All that bathrooms have been updated also. Hurricane-impact windows and doors have all been replaced, providing peace of mind and energy efficiency. Additional upgrades include new flooring, a new roof in 2025, updated house wiring and electrical service panel in 2019, and a complete camera security system. A unique bonus feature is the fully equipped caterer’s kitchen located in the garage — ideal for entertaining, large gatherings, or serious cooking enthusiasts. This home combines timeless care, extensive updates, and resort-style living in one of the area's premier boating communities that features tennis courts, clubhouse, pickleball courts, deep water marina, kayak storage and much more! This is a rare opportunity to own a meticulously maintained and beautifully upgraded home in one of the area’s most desirable waterfront communities.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Andrew Peterson (716-316-3145)
852 MACEWEN DR, OSPREY, FL 34229
$2,395,000339 Days on yellowkey MLS ID: A4659276
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4519 Built: 1992Monthly Fee: $133 Tax: $12,855 (2024)Community: Oaks 2 Ph 2Spa: YesSingle Family
Taxes:$12,855
Remarks: **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**
186 WINDWARD DR, OSPREY, FL 34229
$599,900167 Days on yellowkey MLS ID: N6142087
0 Days Off yellowkey (back on 5/13/2026)
REDUCED by $49,600 (7.6%) on 05/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2505 Built: 1983Monthly Fee: $204 Tax: $7,566 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Taxes:$7,566
Remarks: Under contract-accepting backup offers. Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Brittany Coleman, Pllc (941-539-5023)
447 N SHORE DR, OSPREY, FL 34229
$499,000111 Days on yellowkey MLS ID: A4684009
REDUCED by $16,350 (3.2%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1874 Built: 1964 Tax: $4,243 (2025)Community: Sorrento ShoresSingle Family
Taxes:$4,243
Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Lauren Sisco (904-652-9387)
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