Location: Osprey
Keyword(s): Laurel Nokomis Middle
Keyword(s) Middle School: Laurel Nokomis Middle
Do Not Show Listings
292 TURQUOISE LN, OSPREY, FL 34229
$1,050,00024 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,536
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
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. There is currently no waiting list for either Golf or Sports/Social membership.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
362 MACEWEN DR, OSPREY, FL 34229
$2,249,000158 Days on yellowkey MLS ID: A4676567
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4117 Built: 1998Monthly Fee: $142 Tax: $10,742 (2025)Community: The OaksSingle Family
Taxes:$10,742
Remarks: Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership
1140 BEACHCOMBER CT #11, OSPREY, FL 34229
$525,000115 Days on yellowkey MLS ID: A4683755
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 2005 Tax: $5,401 (2025)Community: Blackburn Point Marina VillageCondo
Taxes:$5,401
Remarks: One or more photo(s) has been virtually staged. Welcome to Blackburn Point Marina Village, where coastal elegance meets maintenance-free living near Sarasota's desired waterfront. Enjoy the boating and waterfront lifestyle you've dreamed of without the million-dollar price tag. This beautifully upgraded townhome features a bright open floor plan with luxury vinyl flooring (2025), plantation shutters and 9-foot ceilings. The gourmet kitchen showcases granite countertops, Craft Maid cabinetry, a KitchenAid gas range, LG refrigerator (2023) and a wine refrigerator, ideal for entertaining. Highlights include a new roof (2025), enclosed sunroom, water filtration/softener system (2024), tankless water heater, motorized hurricane shutters, epoxy garage floor, LiftMaster garage door with camera (2025) and smart home technology. The serene primary suite offers dual vanities, a soaking tub and walk-in shower. Near Casey Key Marina, Blackburn Point Park and Casey Key Fish House & Tiki Bar, this gated community includes resort-style amenities and covers water and gas bill. Your affordable slice of paradise awaits.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Netzel (941-539-0633)
365 S SHORE DR, OSPREY, FL 34229
$1,349,000169 Days on yellowkey MLS ID: N6142101
REDUCED by $31,000 (2.2%) on 05/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1824 Built: 1968 Tax: $7,804 (2025)Community: Sorrento ShoresSingle Family
Taxes:$7,804
Remarks: Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined home remains unaffected by flooding AND IN FLOOD ZONE X, unfolds safely toward the water where EXPANSIVE BAY WINDOWS frame uninterrupted scenery. Step out your back door and hop on your boat for effortless days on the water in a premium location. FULLY FURNISHED! Offering 3 BEDROOMS, 2 FULL BATHROOMS, and 1,846 square feet of true Florida living, this home’s PANORAMIC VIEWS flood it with natural light and blur the line between indoors and out. PGT IMPACT WINDOWS, ELECTRONIC SHUTTERS, rich WOOD PANELING, and CROWN MOLDING lend architectural depth and timeless coastal sophistication, creating a home that feels calm, luminous, and deeply connected to its surroundings. The kitchen features QUARTZ countertops, a GRANITE COMPOSITE SINK, and UPGRADED FIXTURES. CEDAR-accented guest bedroom ceilings, CUSTOM built-in closets throughout, and NEW LIGHTING reflect thoughtful stewardship. ADDITIONAL UPGRADES include a new REVERSE OSMOSIS WATER FILTERATION SYSTEM AND WATER HEATER (2023) and AIR DUCTS (2025). Outdoor living is the centerpiece. The PRIVATE DOCK AND OUTDOOR FIRE PIT are natural extensions of the home, inviting morning coffee, sunset cocktails, and manatee sightings. Boat amenities were meticulously maintained with NEW MOTOR CAPACITORS (2023), and BOAT LIFT CABLES AND DOCK LIGHTS (2024). Lush landscaping in the GENEROUS FRONT YARD enhances curb appeal, while mature trees provide tropical PRIVACY, with plenty of room for a POOL. Homes with this DEPTH, PRIVACY, and INTRACOASTAL ACCESS are RARELY available. This is not simply a WATERFRONT HOME – it is a BOATING LIFESTYLE defined by light, movement, and an ever-changing horizon. Just a 2 minute boat ride to the Intracoastal Waterway, 25 minutes to the Gulf of Mexico and 10 minutes to Casey Key Fish House and Tiki Bar! Call for a private tour of this beauty!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Lisa Asaro (941-725-8626)
1367 THORNAPPLE DR, OSPREY, FL 34229
$579,00016 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
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 Agent: Todd Currey (941-402-6000)
742 HARMS DR, OSPREY, FL 34229
$515,000262 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
$795,00046 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)
18 N CASEY KEY RD, OSPREY, FL 34229
$1,750,000242 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)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000258 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 is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Napolitano (941-993-0025)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$875,000119 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.
5100 JESSIE HARBOR DR #403, OSPREY, FL 34229
$650,000170 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)
120 VILLA DR #120, OSPREY, FL 34229
$497,000430 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 is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Hansel Pitts, Jr. (941-800-6076)
272 FOUR KNOT LN, OSPREY, FL 34229
$1,095,00037 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
$2,395,000334 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**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
447 N SHORE DR, OSPREY, FL 34229
$499,000106 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 Agent: Lauren Sisco (904-652-9387)
236 SAINT JAMES PARK, OSPREY, FL 34229
$2,700,000449 Days on yellowkey MLS ID: A4644125
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 6246 Built: 1986Monthly Fee: $283 Tax: $22,433 (2024)Community: Oaks 2 Ph 1Spa: YesSingle Family
Taxes:$22,433
Remarks: Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly positioned on the 1st hole of the Heron Course, capturing sweeping golf course and clubhouse views—just minutes from Siesta Beach and Casey Key. The main residence offers 4,700+ square feet, complemented by a private 1,500+ square foot guest house—ideal for extended family or long-term guests. Outdoor living is elevated with a pool and spa, outdoor kitchen, private guest laundry, and some of the most captivating views in the community. At The Oaks, coastal sophistication unfolds across 36 championship fairways, tennis and pickleball courts, with endless opportunities for recreation, dining, and connection. Membership required.
Listing Agent: Karin Watt (941-773-1273)
135 TINA ISLAND DR, OSPREY, FL 34229
$3,295,00045 Days on yellowkey MLS ID: A4692366
Bed: 3 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 2572 Built: 1965Monthly Fee: $10 Tax: $12,575 (2025)Community: Sorrento ShoresSpa: NoSingle Family
Taxes:$12,575
Remarks: **EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level includes a 4-Car Garage and provides extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.
1486 LANDVIEW LN, OSPREY, FL 34229
$850,000220 Days on yellowkey MLS ID: D6144630
0 Days Off yellowkey (back on 5/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1869 Built: 1977Monthly Fee: $204 Tax: $7,488 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$7,488
Remarks: Under contract-accepting backup offers. Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout, fully redesigned spa-inspired bathrooms with custom vanities, updated ceilings, recessed lighting, and interior shaker doors. The home was also re-piped for water and sewer, offering both modern comfort and long-term peace of mind. The light-filled living room, accented with elegant shiplap detail, opens effortlessly to the lanai, creating a graceful indoor-outdoor connection. Outside, a private retreat awaits with a resurfaced pool, new screen enclosure, and marble pavers. Generous covered space accommodates lounging, dining, and entertaining, while sliding doors from the primary suite, living room, and family room invite the outdoors in and enhance the home’s open, airy ambiance. The primary suite is a serene escape, thoughtfully positioned for privacy and direct access to the lanai. Custom closet systems throughout the home provide elevated functionality, while the epoxy-finished garage with built-in cabinetry delivers a polished, organized finish. Mature tropical landscaping and six-foot pitch apple plantings create a secluded backyard sanctuary, complemented by stately palms that frame the home with unmistakable Florida elegance. Southbay offers a distinguished, resort-style lifestyle with a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Residents enjoy a heated pool, youth pool, tennis and pickleball courts, shuffleboard, bocce, basketball courts, walking trails, and an Intracoastal waterfront park. For boating connoisseurs, the community-owned deep-water marina provides direct Intracoastal access with no fixed bridges to the Gulf. Exclusive, low-fee boat slips accommodate vessels up to 55 feet and are available only to Southbay owners. A vibrant social calendar and golf-cart-friendly streets make it effortless to enjoy community events, nearby boutiques, waterfront dining, and local beaches. Ideally located near Pine View School—Florida’s #1 charter school and one of the nation’s premier gifted programs—this residence presents a rare opportunity to enjoy luxury living within an active, waterfront enclave. A sophisticated coastal retreat where lifestyle, privacy, and boating converge—welcome to Southbay.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Barbara Teyssier (304-671-6691)
107 SORRENTO DR, OSPREY, FL 34229
$425,000107 Days on yellowkey MLS ID: N6143210
REDUCED by $24,000 (5.3%) on 04/12/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1284 Built: 1963Monthly Fee: $10 Tax: $2,566 (2025)Community: Sorrento ShoresSingle Family
Taxes:$2,566
Remarks: This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)
Listing Agent: Crystal Cosby, Llc (941-882-0070)
854 MACEWEN DR, OSPREY, FL 34229
$3,690,000243 Days on yellowkey MLS ID: A4668918
REDUCED by $100,000 (2.6%) on 05/01/2026
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 9081 Built: 2003Monthly Fee: $133 Tax: $26,109 (2024)Community: Oaks 2 Ph 2Spa: YesSingle Family
Taxes:$26,109
Remarks: One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style. A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools. Experience this home for yourself—take the 3D virtual tour and book your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Joe Murphy (941-780-3260)
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