Location: Osprey
Keyword(s): Laurel Nokomis Middle
Keyword(s) Middle School: Laurel Nokomis Middle
Do Not Show Listings
157 LOOKOUT POINT DR, OSPREY, FL 34229
$875,0002 Days on yellowkey MLS ID: A4694878
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1859 Built: 1981Monthly Fee: $219 Tax: $4,950 (2025)Community: Southbay Yacht & Racquet ClubSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,950
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact glass. A secluded back yard retreat awaits you with a spacious covered lanai looking onto the updated heated self draining pool and the wooded back yard. Some of the home highlights are: UPDATED KITCHEN AND BATHS, PORCELAIN TILE IN THE MAIN LIVING AREAS, IMPACT WINDOWS ABOUT 11-12 YEARS AGO. The owners have continued with the updates including: NEW METAL ROOF 2023, REPLACED MAIN ELECTRICAL PANEL AND ADDED 220 OUTLET FOR FUTURE GENERATOR. ADDED WHOLE HOUSE AIR PURIFICATION 2022, NEW EPOXY GARAGE FLOOR 2020, A/C AND HEAT PUMP SYSTEM 2018, REPLACED 3 DOORS WITH IMPACT GLASS, REPLACED 3 SLIDING GLASS DOORS WITH IMPACT GLASS 2015, COMPLETE POOL AND LANAI RENOVATION INCLUDING HEAT PUMP AND DECK PAVERS 2017, REPLACED GARAGE DOOR WITH IMPACT RESISTANT DOOR AND VENTS. REPLACED APPLIANCES: MICROWAVE 2025, REFRIGERATOR AND WINE COOLER 2024, RANGE, WASHER, DISHWASHER, 2023, HOT WATER HEATER 2023, REPLACED CARPET WITH CERAMIC TILE 2021 AND CUSTOM PLANTATION SHUTTERS THROUGHOUT THE HOUSE. There are more items I haven’t mentioned but you need to come take a look for yourself. There is a detailed list of improvements available. The Southbay community has much to offer! One of the few neighborhoods with its own exclusive marina. Dock space is only available to residents and is offered at very reasonable rates and can accommodate almost any size boat. Southbay is an active community with many clubs and gatherings at the remodeled clubhouse overlooking the marina. The clubhouse features two kitchens, ballroom, fitness center, card room, even a “livingroom” with grand piano. There’s something for everyone! Pickleball courts, tennis courts, bocce ball, community pool, playground, kayak launch and storage. Southbay is also a golf cart community! The Southbay location is in easy reach of shopping, grocery stores, restaurants, main roads, downtown Sarasota and downtown Venice. Local beaches including Nokomis (5 miles away), Siesta Key (10 miles away), Venice (7 miles) are all within an easy drive. Local restaurants including the famous Casey Key Fish House and Tiki bar are close at hand. Come and see what makes this home and Southbay so special!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)
Listing Agent: Pat Williams (941-289-6231)
89 NAVIGATION CIR, OSPREY, FL 34229
$345,0008 Days on yellowkey MLS ID: A4694435
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1449 Built: 2014 Tax: $3,931 (2025)Community: Bay Street VillageCondo
Taxes:$3,931
Remarks: One or more photo(s) has been virtually staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)
Listing Agent: Jozefina Wells (941-993-3051)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000238 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
Tax Year: 2024
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 is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Napolitano (941-993-0025)
5100 JESSIE HARBOR DR #304, OSPREY, FL 34229
$735,00038 Days on yellowkey MLS ID: A4690942
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004 Tax: $6,004 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$6,004
Remarks: Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
292 TURQUOISE LN, OSPREY, FL 34229
$1,050,0004 Days on yellowkey MLS ID: A4694515
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2255 Built: 2001Monthly Fee: $400 Tax: $6,536 (2025)Community: Emerald Woods At Oaks 03 Ph 02Spa: YesSingle Family
Taxes:$6,536
Remarks: This stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located behind the gates of The Oaks Preserve, this maintenance free residence features 3 bedrooms, 2 baths and a 2-car air conditioned garage along with premium finishes throughout. The updated kitchen, equipped with high-end stainless steel appliances, will delight any home chef. The spacious master suite includes a luxurious master bath, walk-in closets, and a sitting area with sliders to the lanai and pool. The expansive outdoor living area is designed for relaxation and entertaining, showcasing an impressive pool and spa, a new outdoor kitchen, new automated hurricane shutters and a view of a tranquil pond. Additional updates include a new roof, hurricane impact PGT windows and sliding doors, new quartz countertops throughout, a water softening and purification system and built-ins in the 3rd bedroom currently used as a combined study/bedroom. Residents of The Oaks enjoy unmatched amenities including two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
353 S SHORE DR, OSPREY, FL 34229
$1,060,00059 Days on yellowkey MLS ID: A4688006
REDUCED by $39,000 (3.5%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1968Monthly Fee: $11 Tax: $3,904 (2025)Community: Sorrento Shores Rep Of 2Spa: NoSingle Family
Taxes:$3,904
Remarks: Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated on an oversized canal-front lot, this move-in ready 3-bedroom, 2-bath home offers quick deep-water access to the Intracoastal and Gulf beyond. Bring your boat, your paddleboards, your fishing gear, and start living the coastal lifestyle immediately. This home is Offered TURNKEY (minus select personal items), has a Private dock with quick open-water access, a 27x40 screened lanai with resurfaced pool for plenty of lazy pool days, and sits on an Oversized .36-acre lot. No need to store your boat trailer off site, there is ample parking for your boat trailer right on your own property. No CDD fees + voluntary HOA only $130/year And the Big-Ticket items have been taken care of: NEW ROOF 2025, NEW SEPTIC SYSTEM 2024, NEW POOL CAGE 2025 SEWER PIPES RELINED 2023-2024, IMPACT WINDOWS 2018, NEW POOL HEATER 2025, NEW WATER HEATER 2024 Newer A/C 2018 Updated baths + fresh interior finishes 2025 Cruise by boat to Casey Key Fish House, Pops Sunset Grill, Snake Island, Midnight Pass, Venice waterfront restaurants, and the Gulf of Mexico — all from your own backyard. This is not just a home… It’s the waterfront lifestyle buyers dream about!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Phyllis Coviello (941-408-3265)
314 S SHORE DR, OSPREY, FL 34229
$1,649,0005 Days on yellowkey MLS ID: TB8510971
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3853 Built: 1981Monthly Fee: $15 Tax: $8,819 (2025)Community: Sorrento Shores Unit 1Spa: NoSingle Family
Taxes:$8,819
Remarks: Rare Gulf-access waterfront opportunity in desirable Sorrento Shores in Osprey. This spacious residence is set on a generous 0.54-acre waterfront lot with a private dock, screened pool, outdoor kitchen/grill area, paver patio, mature landscaping, and peaceful canal views. The home offers 3 bedrooms, 3 full baths, 3,853 sq ft, and a large flex room currently used as a studio with possible 4th bedroom potential. The open ranch-style layout includes comfortable living, dining, and entertaining spaces filled with natural light. The updated kitchen and bar area feature Viking Professional double ovens, a Viking Professional gas stove, Sub-Zero refrigerator, newer dishwasher, and microwave. Additional spaces include a private office with built-in cabinetry, large flex room, and an air-conditioned tackle/hobby/storage room with an additional Sub-Zero refrigerator. Major system updates noted by seller include a newer roof, full-house generator, impact windows and doors, two AC systems, new central vacuum system, tankless water heater, fireplace, and propane service for the grill, stove, dryer, fireplace, tankless water heater, and full house generator. Located near Casey Key, Nokomis Beach, Venice, Sarasota, marinas, dining, shopping, golf, parks, and coastal amenities. Property is being sold As-Is with right to inspect. Seller exclusions include seller’s personal property, all potted plants, and the backyard swing.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
4428 CONCHFISH LN, OSPREY, FL 34229
$548,000346 Days on yellowkey MLS ID: A4656074
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1861 Built: 2018Monthly Fee: $147 Tax: $5,936 (2024)Community: Palms/Casey KeySpa: NoSingle Family
Taxes:$5,936
High School: Pine View School
Remarks: Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a stylish backsplash, a large walk-in pantry, and stainless-steel appliances. The master retreat offers a tranquil area with a spacious bedroom. Plantation shutters and 18x18 tiles complemented by hard floors throughout the entire house. The residence has hurricane shutters, Low-E windows, and a generator hook-up. A large 26x10 covered lanai provides space for relaxing and entertaining. The Palms at Casey Key is a lovely neighborhood with low HOA fees that offers a sense of privacy. Imagine the ease of having your boat just minutes away at the nearby Casey Key Boat Launch, ready whenever you are. They say location is everything, and this home truly delivers on that promise. Ideally situated, it offers immediate access to everyday conveniences: restaurants, grocery stores, and a quick connection to I-75. Dog lovers will appreciate the brand-new dog park nearby, perfect for playtime and socializing. Just under a mile from your front door, the Casey Key Boat Launch and the lively Tiki Bar invite you to unwind and enjoy days by the water. Families will love the close proximity to the prestigious Pine View School, renowned for academic excellence and ranked as the number one high school in Florida, the second-highest elementary school in the US, and the third-highest middle school in the US. Beyond the neighborhood, you'll find easy access to Siesta Key Beach, top-tier golf courses, vibrant cultural attractions, and exciting entertainment options. With low HOA fees and no CDD fees, this home offers the freedom to live your dream Florida lifestyle, without the rising costs of new construction. Move-in ready and like-new, this residence is a perfect blend of character and delightful charm. Store your boat, enjoy the community, and embrace life with ease and comfort. Don’t miss your chance to claim your own piece of paradise!
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Mariana Georgieva (941-809-0416)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$875,00099 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.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
1337 COPPERWOOD DR, OSPREY, FL 34229
$550,000242 Days on yellowkey MLS ID: A4666722
2 Days Off yellowkey (back on 5/18/2026)
REDUCED by $19,000 (3.3%) on 04/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2172 Built: 2004Monthly Fee: $397 Tax: $4,420 (2025)Community: Willowbend Phase 3Spa: NoSingle Family
Taxes:$4,420
Remarks: This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.
754 PINE RUN DR #754, OSPREY, FL 34229
$269,00019 Days on yellowkey MLS ID: A4693150
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1379 Built: 1973 Tax: $3,176 (2025)Community: Pine Run ISpa: NoCondo
Taxes:$3,176
Remarks: One or more photo(s) has been virtually staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless indoor-outdoor connection rarely found in condominium living. The thoughtfully designed floorplan delivers a tranquil, nature-inspired experience—particularly from the south bedroom wing, where walls of glass frame peaceful wooded views, offering a remarkable sense of serenity and privacy. Beautifully modernized for today’s lifestyle, the kitchen and living spaces have been opened into a sophisticated great-room design, ideal for entertaining and everyday comfort. Timeless Saltillo Mexican tile flooring runs throughout, adding warmth, texture, and character. Additional conveniences include covered carport parking, a large private storage closet, and tasteful updates that make this residence completely move-in ready. Residents enjoy an impressive collection of resort-style amenities, including two heated pools—one dramatically overlooking a wildlife-filled lagoon—along with two cedar saunas, a fitness center, a Florida-style clubhouse, scenic walking trails, BBQ gas grills, an outdoor gas fireplace, kayak storage, and tennis and pickleball courts. Perfectly positioned for an active coastal lifestyle, this premier location places you just minutes from Nokomis Beach, Oscar Scherer State Park, multiple kayak launches, a public boat ramp, and the Legacy Trail, offering miles of biking and recreation connecting Venice and Sarasota. Nearby favorites include Casey Key Fish House, Historic Spanish Point, waterfront dining, medical facilities, and endless local conveniences. Everyday living couldn’t be easier—walk to Publix, CVS, Ace Hardware, shops, restaurants, fitness centers, Walmart, and the Post Office, or enjoy quick access to everything the area has to offer without needing a car. Families will appreciate proximity to the highly acclaimed Pine View School for the Gifted—the only standalone public gifted school in Florida and consistently ranked among the state’s best. Combining exceptional privacy, thoughtful design, resort-style amenities, and unmatched convenience, this is a rare opportunity to own a distinctive, beautifully updated home in one of the area’s most desirable locations—perfect for those seeking the ideal balance of nature, accessibility, and modern coastal living.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Sasha Volosevych (971-703-0307)
127 PARK TRACE BLVD, OSPREY, FL 34229
$795,00026 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)
5100 JESSIE HARBOR DR #403, OSPREY, FL 34229
$650,000150 Days on yellowkey MLS ID: A4676382
REDUCED by $29,900 (4.4%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2004Monthly Fee: $1,027 Tax: $5,647 (2025)Community: Blackburn Harbor ResidencesCondo
Taxes:$5,647
Remarks: This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pullouts and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking, or your gourmet meal preparation, a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your primary retreat vie for your attention thanks to the shimmering intracoastal front and center. Generous in size, the main retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are under the building and out of the elements, adding to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, and fishing. Boat slips are available on a first-come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path and pretty greenspace areas. Ideally close to shopping, dining, the crystal sand beaches and famed Oscar Scherer State Park, which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming, and the best part is the proximity, just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.
Listing Agent: Cindy Migone (941-812-7438)
562 OAK BAY DR, OSPREY, FL 34229
$530,00033 Days on yellowkey MLS ID: A4690387
1 Days Off yellowkey (back on 5/20/2026)
REDUCED by $30,000 (5.4%) on 05/09/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2414 Built: 1995Monthly Fee: $25 Tax: $3,524 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$3,524
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees. The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026). Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard. The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower. The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows. The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience. A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring. At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense). Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018). This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch. Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more. This is a home you need to experience in person. Schedule your private showing today!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Julianna Burns (941-800-7653)
140 SUGAR MILL DR, OSPREY, FL 34229
$1,399,00081 Days on yellowkey MLS ID: A4684805
0 Days Off yellowkey (back on 5/3/2026)
REDUCED by $296,000 (17.5%) on 04/24/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3286 Built: 1989Monthly Fee: $483 Tax: $12,040 (2025)Community: OaksSpa: YesSingle Family
Taxes:$12,040
Remarks: Under contract-accepting backup offers. SELLERS SAY SELL! BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining - making any occasion a treat! The private primary suite is "magazine worthy" - a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan - offering privacy with three additional suites - perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage - and you'll be the envy of the neighborhood with the "thought of everything" laundry room and spacious garage. Step outside to exceptional outdoor living - designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you'll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful - it's been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks - Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay - perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you're just minutes from Sarasota's outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida's ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)
Listing Agent: Monica Verinder (941-704-4040)
102 WINDWARD DR, OSPREY, FL 34229
$650,000192 Days on yellowkey MLS ID: A4671793
0 Days Off yellowkey (back on 5/7/2026)
REDUCED by $40,000 (5.8%) on 04/26/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2134 Built: 1986Monthly Fee: $219 Tax: $3,540 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$3,540
Remarks: NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking. Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: David Cyr (941-400-4691)
120 VILLA DR #120, OSPREY, FL 34229
$497,000410 Days on yellowkey MLS ID: N6138441
REDUCED by $13,000 (2.5%) on 04/25/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1404 Built: 1978Monthly Fee: $529 Tax: $5,056 (2025)Community: Sorrento Villas 1Villa
Taxes:$5,056
Remarks: Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.
Listing Agent: Hansel Pitts, Jr. (941-800-6076)
619 OAK RIVER CT, OSPREY, FL 34229
$609,90016 Days on yellowkey MLS ID: A4692331
0 Days Off yellowkey (back on 5/16/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2047 Built: 1997Monthly Fee: $25 Tax: $5,484 (2025)Community: Bay Oaks EstatesSpa: NoSingle Family
Taxes:$5,484
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)
Listing Agent: Ross Fishman (763-443-1761)
742 HARMS DR, OSPREY, FL 34229
$515,000242 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
Remarks: Beautifully renovated and now offered at a newly reduced price, this turnkey property is a fantastic opportunity with motivated sellers. Set on just over half an acre along a private, tree-lined street the home is surrounded by lush tropical landscaping that creates a peaceful and secluded feel. Inside you’ll find a spacious layout with modern finishes and seamless indoor-outdoor living with a heated pool and screened lanai. The home has been fully updated and has a strong history as a successful income-producing rental. Major improvements include a full interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), HVAC (2023), and water heater, well pump, and garage door opener (2024), plus an automated pool cleaner and septic flush (2025). Ideally located between Sarasota and Venice, you’re just minutes from beaches, dining, and shopping. Oscar Scherer State Park sits directly across the street for nature trails and birdwatching, and Legacy Trail (Osprey Junction Trailhead) is only three minutes away, making this a great spot for outdoor enthusiasts. With NO HOA and plenty of space for a boat or RV, this property offers updated comfort, privacy, and flexibility perfect as a full-time home, seasonal retreat, or investment.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Tiffany Stonis (941-204-5239)
272 FOUR KNOT LN, OSPREY, FL 34229
$1,095,00017 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)
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