Location: Osprey , 34229
Do Not Show Listings
252 SUN AIR CIR, OSPREY, FL 34229
$215,00059 Days on yellowkey MLS ID: A4683143
REDUCED by $10,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1979Monthly Fee: $215 Tax: $1,087 (2025)Community: ArborsManufactured Home
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,087
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Welcome to easy Florida living in The Arbors of Osprey! This beautifully updated 2-bedroom, 2-bath manufactured home offers modern finishes, thoughtful upgrades, and a spacious open layout designed for comfort and entertaining. Step inside to discover newer tile and laminate flooring flowing throughout the home. The remodeled kitchen is a true showstopper, featuring raised-panel cabinetry, quartz countertops, a striking stone backsplash, center island, pantry, and plenty of prep and storage space. The open floor plan seamlessly connects the kitchen to the dining area and spacious family room, perfect for gatherings or relaxed everyday living. The spacious primary suite offers a walk-in closet and an updated ensuite bath complete with dual sinks in a new vanity, newer lighting and mirror, and a walk-in shower. The guest bedroom is versatile and inviting with a convenient Murphy bed, while the second bath has been tastefully updated with a tub/shower combination, new vanity lighting, and mirror. Enjoy Florida’s sunshine year-round in the bright Florida room filled with loads of windows, or unwind on the screened, enclosed lanai. Plantation shutters throughout the home. Additional highlights include a utility shed with washer and dryer, non-skid surface in lanai and driveway. Major system updates for peace of mind include a 6-year-old roof with transferable warranty, newer A/C, tankless hot water heater, 98% plywood subflooring, and cement board subfloor in the kitchen and dining room. Located in the desirable Arbors community in Osprey, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. This fully furnished, move-in ready home blends quality upgrades with relaxed Florida charm. Schedule your private showing today and start enjoying the lifestyle you deserve!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Karen Geiger (941-928-8889)
260 HIDDEN BAY DR #304, OSPREY, FL 34229
$694,00062 Days on yellowkey MLS ID: N6142969
REDUCED by $5,000 (0.7%) on 04/14/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1950 Built: 2019 Tax: $6,342 (2025)Community: Edgewater/Hidden Bay Ph 2 BldgSpa: YesCondo
Taxes:$6,342
Elementary School: None
High School: None
Middle School: None
Remarks: The Boca Residence: Spacious Living & Resort Style Discover a condominium that offers the true scale and functionality of a private home. The Boca floor plan features a thoughtfully designed two-bedroom plus den, two-and-a-half-bathroom layout, perfect for those who want the ease of condo living without sacrificing space. Whether you are looking for a full-time residence or a spacious seasonal getaway, this home provides a comfortable and highly livable environment. The experience begins with a proper foyer entry that opens into expansive living and dining areas, ideal for hosting family and friends. A dedicated den offers great flexibility as a home office, hobby room, or guest space. This residence is designed for privacy with a split-bedroom configuration, while the additional powder room adds everyday convenience for guests. High ceilings, generous room sizes, and multiple walk-in closets are complemented by a large private terrace that extends your living space outdoors. Beyond the front door, the community offers a host of resort-style amenities. Enjoy a heated pool and spa, a social clubhouse, a fitness center, and courts for both tennis and pickleball. A scenic boardwalk leads to outdoor grilling stations and a tropical Tiki hut gathering area, perfect for weekend get-togethers. To truly experience the lifestyle this home offers, we invite you to schedule your private tour during the sunset hour to see the incredible views that make this residence so special.
Listing is courtesy of: ENGEL & VOELKERS VENICE DOWNTOWN (941-388-9800)
Listing Agent: Janice Martin (941-225-9843)
1811 HIGHLAND RD, OSPREY, FL 34229
$422,000171 Days on yellowkey MLS ID: TB8443161
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 1997Monthly Fee: $150 Tax: $4,299 (2024)Community: Towns-End ShoresSpa: NoTownhouse
Taxes:$4,299
Tax Year: 2024
Remarks: PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches. Walking distance to Casey Key Mainland (Chef Rolfs), private community Shoreland Park & Oscar Scherer State Park. Minutes away from COSTCO, Publix, Target, Richard's, YMCA Potter Park, waterfront dining (Casey Key Fish House & Tiki bar - waterfront , Spanish Point restaurant & Tiki Bar. The townhouse is close to Laurel Rd and Sarasota Memorial Hospital. Property is managed by owner. Timely response to accommodate your needs. Summary of amenities: PARKING: 2-CAR TANDEM GARAGE HOA PRIVATE COMMUNITY 1 BLOCK FROM INTERCOASTAL SCREENED BALCONY CEILING FANS VAULTED CEILING CENTRAL AIR UPGRADED TALL CABINETS GRANITE COUNTERTOP STAINLESS STEEL APPLIANCES CONVECTION RANGE/OVEN/AIRFRYER MICROWAVE DISHWASHER IN-SINK DISPOSAL SMART REFRIGERATOR DINING ROOM & FAMILY ROOM MASTER BEDROOM WITH WALK-IN CLOSET MASTER BATH GUEST BEDROOM ADDITIONAL STORAGE IN LOWER FLOOR OR GARAGE AIR CONDITIONING WASHER/DRYER SPRINKLER SYSTEM COMMUNITY SWIMMING POOL WITH LOUNGE CHAIRS + USE OF CASEY KEY MAINLAND POOL WALK/BIKE TO TOP RATED PINEVIEW SCHOOL, WALLMART, POST OFFICE, LEGACY BIKE TRAIL CLOSE TO SIESTA KEY, NOKOMIS BEACH, VENICE BEACH, OSCAR SCHERER STATE PARK HUGE FURNISHED BONUS ROOM ON FIRST FLOOR OUTDOOR GRILL Turn-key ready!
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
1019 SCHERER WAY, OSPREY, FL 34229
$735,000107 Days on yellowkey MLS ID: N6142144
0 Days Off yellowkey (back on 1/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2498 Built: 2004Monthly Fee: $120 Tax: $6,107 (2025)Community: Rivendell The WoodlandsSpa: YesSingle Family
Taxes:$6,107
Remarks: Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window overlooking the lanai. Large living room with tray ceilings. Vaulted ceilings in the family room with a built-in as the focal point. Formal dining room with a palladium window allowing the sunlight in. Wow! describes the spacious screened lanai featuring a salt water heated in ground pool w/spa. Plenty of space for dining, entertaining and games. Backing to the preserve with additional fenced in yard area. Home is situated less than a mile from the Legacy Bike Trail, and nearby Oscar Scherer State Park, Nokomis beach, the Gulf historic downtown Venice, shopping, restaurants & schools. Freshly painted. Bright & Airy. One of the lowest HOA fees around. 3 car garage with EV charging station. Owned Tesla solar panels that keep the electric bills very low. The home checks all the boxes and a must see!
Listing is courtesy of: CENTURY 21 SCHMIDT REAL ESTATE (941-485-0021)
Listing Agent: Christine Appice (908-692-5062)
75 OSPREY POINT DR, OSPREY, FL 34229
$1,695,000152 Days on yellowkey MLS ID: A4672439
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4001 Built: 1983Monthly Fee: $967 Tax: $14,229 (2024)Community: OaksSpa: NoSingle Family
Taxes:$14,229
Remarks: **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as the “Park Avenue” of The Oaks Golf & Country Club. A gorgeous new 4ft x 4ft “Celini Agento Italian” tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The nearby, private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. The Oaks-Bayside is a truly 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 AERIAL VIDEO**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
570 BLACKBURN POINT RD #35, OSPREY, FL 34229
$99,50023 Days on yellowkey MLS ID: A4687906
0 Days Off yellowkey (back on 4/14/2026)
Bed: Bath: 0.0 Monthly Fee: $391 Tax: $402 (2025)Community: Dry Slips At Bellagio VillageDock-Rackominium
Taxes:$402
Remarks: Under contract-accepting backup offers. Welcome to this quality high end marine facility. Take confidence knowing that your boat is stored in this completely enclosed hurricane rated boat building. Your privately owned boat rack offers unlimited in and out splashes, outside work racks, ethanol free fuel, independent detailing contractors, a full-service shop including deli, drinks, ice, bait and other miscellaneous services. The docks have fillet tables, pump out station, fresh water hoses and electrical. This spacious slip holds a boat 27.5' in length, 10' wide and 10.5 feet in height. Open seven days a week, your boat can be splashed within an hour's notice. Conveniently located just minutes from midnight pass and centrally located between Venice and Sarasota. Master Association fees are included in the hoa fees.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: David Babel (941-232-1614)
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000198 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)
120 CANDYCE DR, OSPREY, FL 34229
$650,000166 Days on yellowkey MLS ID: A4667108
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2103 Built: 1962 Tax: $10,123 (2024)Community: Sorrento ShoresSingle Family
Taxes:$10,123
Remarks: Under contract-accepting backup offers. This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation for your renovation. Whether you’re an investor looking for your next project or a buyer eager to build sweat equity in a prime waterfront community, 120 Candyce Drive delivers both value and potential in one of Sarasota County’s most sought-after coastal neighborhoods. Ideally located just minutes from Nokomis Beach, Casey Key, and popular waterfront dining, this home combines location and opportunity with no HOA restrictions. Turn this waterfront fixer-upper into your stunning Florida escape.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
135 WOODLAND PL, OSPREY, FL 34229
$269,00021 Days on yellowkey MLS ID: A4687664
1 Days Off yellowkey (back on 4/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1979 Tax: $2,660 (2025)Community: Pine Run IiCondo
Taxes:$2,660
Remarks: Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden view with four patios that includes a rear lanai enclosed with sliding vinyl windows. A unique inner atrium with aquarium style glass windows adds architectural interest and abundant natural light while maintaining privacy. The unit features easy to maintain custom tile floors on the diagonal throughout with wood floor inspired ceramic tiles in the bedrooms. Since 2023, unit updates include all new kitchen appliances, new faucets, new PEX water lines, a new water heater as well as new paint inside and out. The unit also includes a deeded carport parking space and two storage closets. Onsite resort style amenities include two heated pools (one overlooking a lagoon), two cedar saunas, a fitness room, Florida style clubhouse, walking trails, BBQ gas grill, outdoor gas fireplace, kayak storage, pickleball and tennis courts. Within a mile is the Pine View School (the only standalone public gifted school in the state), Oscar Scherer State Park, 2 kayak launches, a public boat ramp, Casey Key Fish House, Walmart and a Post Office. Easily walk to Publix, Ace Hardware, CVS, shops and restaurants or bike to the Legacy Trail and Nokomis Beach. Exceptional privacy, easy access, and a premier location make this residence an outstanding opportunity. Priced to sell!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Kim Azar-Calka (239-216-6205)
1602 SOUTHBAY DR, OSPREY, FL 34229
$974,900216 Days on yellowkey MLS ID: A4665288
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2980 Built: 1986Monthly Fee: $204 Tax: $9,955 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$9,955
Remarks: Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical landscaping and stately curb appeal immediately set the tone. Step inside to a generously sized home designed for both relaxation and entertaining. Open living areas, large windows, and high ceilings create an airy, welcoming atmosphere, while the refreshed interiors offer a clean, move-in-ready feel. The updated kitchen serves as the heart of the home, providing both style and functionality for everyday living and hosting guests. The interior flows seamlessly into the private outdoor oasis, where the recently updated pool and jacuzzi invite you to enjoy endless days under the Florida sun. Whether hosting friends for a casual barbecue, unwinding with a sunset soak, or enjoying your morning coffee poolside, this space perfectly embodies Florida’s indoor-outdoor lifestyle. Positioned on a corner lot, the home offers exceptional privacy, light, and space—ideal for family gatherings or a peaceful retreat. Spacious bedrooms provide comfort for both owners and guests. A washer and dryer convey with the sale, along with a brand-new pool table, adding both convenience and entertainment value. Life in Southbay Yacht & Racquet Club is more than just owning a home—it’s embracing a lifestyle. Enjoy access to the deep-water marina with Gulf access, tennis and pickleball courts, a vibrant social calendar, fitness amenities, and waterfront strolls. Just minutes away are the pristine beaches of Siesta Key and Nokomis, along with world-class dining and boutique shopping. Here, every day truly feels like vacation.
Listing Agent: Thomas Kiessling (941-920-1678)
854 MACEWEN DR, OSPREY, FL 34229
$3,790,000183 Days on yellowkey MLS ID: A4668918
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)
1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229
$599,00013 Days on yellowkey MLS ID: C7524397
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2006 Built: 2004Monthly Fee: $980 Tax: $6,502 (2025)Community: Blackburn Harbor Waterfront ViCondo
Taxes:$6,502
Remarks: Welcome home! This GULF ACCESS, WATERFRONT condo in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A CANAL—delivering unmatched PRIVACY, VAULTED ceilings, and MILLION DOLLAR WATER & SUNSET VIEWS that feel like a daily postcard. Lush tropical landscaping welcomes you to a private side entrance, while the building’s exclusive setting—just four units total—places you in one of the most desirable locations within the community. Perfectly situated at the edge of the MARINA, you are just STEPS from your BOAT, making it effortless to enjoy GULF ACCESS and endless days exploring nearby WATERWAYS, waterfront DINING, and hidden gems like Snake Island. Inside, this residence blends comfort and coastal elegance with a thoughtfully designed SPLIT FLOOR PLAN for ultimate privacy. The home features warm COASTAL decor, NEUTRAL PAINT, NEW KITCHEN APPLIANCES, GRANITE COUNTERTOPS, SOLID WOOD CABINETRY, custom light fixtures, and window treatments throughout. The open-concept living space flows seamlessly to a LARGE SCREENED LANAI overlooking the water, community park, and glowing SUNSET skies. FURNISHINGS ARE OPTIONAL. Set within a GATED, FINANCIALLY SOUND community spanning approximately 11 acres, residents enjoy an amenity-rich, resort-style lifestyle including a HEATED POOL, CLUBHOUSE, FITNESS ROOM, TENNIS & PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, BBQ GAZEBO, and scenic walking paths surrounded by lush Florida foliage. The vibrant social calendar offers something for everyone—water aerobics, monthly happy hours, bingo/game nights, pickleball club, book club, and more. Ideally located near US-41, this home offers convenient access to Nokomis Beach, Oscar Scherer State Park, the Legacy Trail, Downtown Venice, Downtown Sarasota, I-75, and Sarasota Memorial Hospital Venice Campus—placing the very best of Florida living right at your fingertips. Whether you're boating to the Gulf, enjoying sunset views from your lanai, or embracing the active waterfront lifestyle, this is truly the Florida Dream come to life. Schedule your private showing today! PLEASE CLICK ON THE VIDEO OF THE UNIT.
Listing is courtesy of: DOWNING FRYE REALTY, INC. (239-261-2244)
Listing Agent: Mackenzie Davis-Mahan (941-993-3272)
480 ORISKANY CT, OSPREY, FL 34229
$1,599,00049 Days on yellowkey MLS ID: A4684136
REDUCED by $96,000 (5.7%) on 04/12/2026
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3208 Built: 1999Monthly Fee: $142 Tax: $6,365 (2024)Community: The Oaks ClubSpa: NoSingle Family
Taxes:$6,365
Middle School: Sarasota Middle
Remarks: Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A well -appointed kitchen opens seamlessly to a family gathering areas, creating an effortless flow for hosting family and friends. Step outdoors to your private oasis and serene dream backyard. A new roof and pool cage (2023) have been added. Living in the Oaks Club means enjoying two championship golf courses,12 har-tru tennis courts, pickleball courts, gorgeous croquet lawns fitness amenities which Junior Olympic size heated pool and an active social calendar- all just minutes away from the cultural vibrancy of downtown Sarasota and the Gulf Coast's world renowned Siesta Beach. Membership in the Oaks Club, Sarasota's premier golf and Country club is required for home ownership.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Susan Pelton (941-321-1007)
1486 LANDVIEW LN, OSPREY, FL 34229
$850,000160 Days on yellowkey MLS ID: D6144630
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: 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)
4226 FRONTIER LN #103, OSPREY, FL 34229
$319,00013 Days on yellowkey MLS ID: A4687965
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1135 Built: 2018Monthly Fee: $475 Tax: $3,542 (2025)Community: Bay Street VillageCondo
Taxes:$3,542
Remarks: Coastal convenience meets effortless living, just minutes from Siesta Key, America’s #1 beach. Welcome to 4226 Frontier Lane, a beautifully maintained 2-bedroom, 2-bath walk-up condo in the gated community of Bay Street Village, offering exceptional value and an easy Florida lifestyle. Built for peace of mind with hurricane impact windows concrete-block construction. A private ground-level garage provides added convenience and storage. Upstairs, the bright, open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. The well-appointed kitchen features 42" cabinetry, granite countertops, stainless steel appliances, and a spacious walk-in pantry, seamlessly flowing into the dining and living areas. Step out onto your large, screened-in lanai to enjoy peaceful mornings or evening cocktails. The generously sized primary suite offers a walk-in closet and an ensuite bath with dual vanities and a tiled walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Ideally located in Osprey, between Sarasota and Venice, you’ll enjoy a quiet, tucked-away setting with shopping, dining, and daily conveniences just minutes away. Bay Street Village residents enjoy resort-style amenities including a heated pool, fitness center, and clubhouse. With reasonable HOA fees covering exterior maintenance, roof, water, sewer, and gated access (and no flood insurance required) this is truly low-maintenance ownership at its best. Perfect as a full-time residence, seasonal escape, or investment opportunity this is Florida living, simplified.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kate Kwiecinski (412-477-9720)
140 SUGAR MILL DR, OSPREY, FL 34229
$1,695,00041 Days on yellowkey MLS ID: A4684805
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: 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)
7303 JESSIE HARBOR DR #7303, OSPREY, FL 34229
$474,900285 Days on yellowkey MLS ID: D6142543
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1883 Built: 1985 Tax: $4,800 (2024)Community: Heron HouseCondo
Taxes:$4,800
Remarks: PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation. Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area! When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you. Take the elevator to your nearby 2 assigned parking spots under the building. Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!
Listing is courtesy of: KW COASTAL LIVING (941-473-7399)
Listing Agent: Toy Coxey (941-662-0010)
120 VILLA DR #120, OSPREY, FL 34229
$510,000370 Days on yellowkey MLS ID: N6138441
REDUCED by $5,000 (1.0%) on 04/01/2026
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)
472 PARK TRACE BLVD, OSPREY, FL 34229
$609,00080 Days on yellowkey MLS ID: A4680326
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 2002Monthly Fee: $58 Tax: $5,925 (2025)Community: Park Trace EstatesSingle Family
Taxes:$5,925
Remarks: Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. Park Trace Estates has low HOA fees, and is in a prime location close to top-rated schools, shopping, restaurants, Legacy Trail, Oscar Scherer State Park, and Gulf Coast beaches.
Listing is courtesy of: SUNDANCE REAL ESTATE SERVICES (941-780-6710)
Listing Agent: Damon Zuchelli (941-448-5686)
1116 BEACHCOMBER CT #3, OSPREY, FL 34229
$545,00017 Days on yellowkey MLS ID: A4688310
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 2005Monthly Fee: $1,133 Tax: $5,376 (2025)Community: Blackburn Point Marina VillageCondo
Taxes:$5,376
Remarks: LOCATION, LOCATION, LOCATION! Nestled within the highly desirable gated enclave of Blackburn Point Marina Village, this beautifully maintained 3-bed, 2.5 bath residence is ready to welcome its new owners. This bright and airy two-story unit features soaring ceilings and a spacious open floor plan, creating an inviting and comfortable living environment. The main living areas are enhanced with tile flooring and flow seamlessly into a well-appointed kitchen, complete with Corian countertops, a breakfast bar, center island, closet pantry, and stainless-steel appliances, perfect for both everyday living and entertaining. The dining area features pocketing sliders that extend the living space to the enclosed lanai, already plumbed for a full outdoor kitchen, offering the ideal indoor-outdoor Florida lifestyle. The primary suite is conveniently located on the ground floor and offers a private retreat with an ensuite bathroom featuring dual vanities, a garden tub, and a walk-in shower. Upstairs, two additional bedrooms and a full bath provide privacy and comfort for guests or family. Step outside to the patio, an ideal setting to relax and enjoy a quiet afternoon or evening cocktail in the Florida sunshine. Additional features include an oversized one-car garage with under-stair storage, a new A/C system (2025), and a new roof (2025), providing peace of mind for years to come. Residents of Blackburn Marina Village enjoy access to a heated community pool, a fully equipped outdoor kitchen, and a vibrant social calendar for those who wish to participate. Ideally located with easy access to Gulf beaches, Blackburn Point Marina, dining, and shopping, this exceptional property truly offers the best of Florida living!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Christine Green (941-914-2463)
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