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.
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.
Property Details
Price:
$650,000
MLS #:
A4671793
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SOUTHBAY YACHT & RACQUET CLUB
Neighborhood:
34229osprey
Listed Date:
Nov 19, 2025
Finished Sq Ft:
2,134
Total Sq Ft:
3,000
Lot Size:
15,778 sqft / 0.36 acres (approx)
Year Built:
1986
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Vinyl
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Washer Hookup
Levels
One
Exterior
Architectural Style
Florida
Attached Garage YN
1
Community Features
Boat Slip, Dock, Intracoastal Waterway, Marina, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, No Truck/RV/Motorcycle Parking, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
Irrigation System, Lighting, Outdoor Shower, Rain Gutters, Sliding Doors, Sprinkler Metered
Garage Spaces
2
Lot Features
Cleared
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Ground Level, Off Street, Oversized
Patio And Porch Features
Covered, Deck, Patio, Screened
Roof
Tile
Waterfront Features
Waterfront
Financial
HOA Fee
$657
HOA Fee Frequency
Quarterly
HOA Includes
Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Recreational Facilities
HOA Name
Rachelle Freed
HOA Phone
(941)966-4237
Tax Year
2024
Taxes
$3,540
Map
Community
- Address102 WINDWARD DRIVE OSPREY FL
- SubdivisionSOUTHBAY YACHT & RACQUET CLUB
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY; LAKE VISTA
- LAKE VISTA
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SORRENTO VILLAS 2
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of May 06, 2026
109
Single Family Listed
142
Avg DOM
461
Avg $ / SqFt
$1,398,004
Avg List Price
Property Summary
- Located in the SOUTHBAY YACHT & RACQUET CLUB subdivision, 102 WINDWARD DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $650,000 and features 3 beds, 3 baths, and has approximately 2,134 square feet of living space, and was originally constructed in 1986. The current price per square foot is $305. The average price per square foot for Single Family listings in OSPREY is $461. The average listing price for Single Family in OSPREY is $1,398,004. To schedule a showing of MLS#a4671793 at 102 WINDWARD DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of WILLIAM RAVEIS REAL ESTATE. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 102 WINDWARD DRIVE
OSPREY, FL