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Front of the house, street view.

102 Windward DriveOsprey, FL, 34229

3beds
3baths
2,134sqft
Single Family Residence
Built in 1986
$657 Quarterly HOA Fee
$565,000
Sold
Price per sqft
$265
Sold on
Jun 4, 2026
MLS #A4671793Updated Jun 4, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
102 Windward Drive
City
Osprey
State
FL
ZIP code
34229
Year built
1986
New construction
No
Faces
East
Rooms
9
Living area
2,134 sqft
Total building area
3,000 sqft
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 7, 2026 at 3:00 PM EST

Price & sale history

EventPrice
Listed for saleMLS #TB8556740$1,047,000
SoldMLS #A4671793$565,000
Price reducedMLS #A4671793$650,000Change: −18.8%−$150,000
Listed for saleMLS #A4671793$800,000
History may be incomplete.
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Location

Front of the house, street view.
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