102 WINDWARD DRIVE OSPREY, FL 34229

update time: 04/15/2026 01:53:46

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.

From US 41 turn onto Southbay Dr., continue through the community and take a right onto Windward Dr. 102 Windward is on the left. Alternatively, from US 41, turn onto Blackburn Point Road, then turn left onto Southbay Drive, followed by an immediate left onto Windward Drive. 102 Windward is on the left.

Property Details

Nearby Properties

Condominium Active

211 WOODLAND DRIVE UNIT 211 OSPREY, FL 34229

2 Beds0/2Baths1,387sqft1980 built

$200,000.00

Single Family Residence Active

123 S WIGGINS ROAD PLANT CITY, FL 33566

4 Beds1/2Baths2,816sqft2007 built

$950,000.00

Manufactured Home Active

238 PALM AIR DRIVE OSPREY, FL 34229

2 Beds0/2Baths1,948sqft1986 built

$179,900.00

Single Family Residence Active

172 SEA ANCHOR DRIVE OSPREY, FL 34229

3 Beds0/3Baths2,993sqft1977 built

$895,000.00

Condominium Active

244 WOODLAND DRIVE UNIT 244 OSPREY, FL 34229

2 Beds0/2Baths1,483sqft1980 built

$200,000.00

Single Family Residence Active

652 N JACKSON STREET EAGLE LAKE, FL 33839

2 Beds0/1Baths648sqft1957 built

$165,000.00

Condominium Active

6311 NEWTOWN CIRCLE UNIT 11B2 TAMPA, FL 33615

2 Beds1/2Baths1,260sqft1979 built

$155,000.00

Single Family Residence Active

312 YACHT HARBOR DRIVE OSPREY, FL 34229

3 Beds0/4Baths4,596sqft1978 built

$1,995,000.00

Townhouse Active

4911 N NEBRASKA AVENUE TAMPA, FL 33603

3 Beds1/3Baths2,663sqft2021 built

$575,000.00

Condominium Active

6323 NEWTOWN CIRCLE UNIT 23A1 TAMPA, FL 33615

3 Beds1/2Baths2,012sqft1979 built

$159,000.00

Condominium Active

3711 W IOWA AVENUE UNIT 214 TAMPA, FL 33611

2 Beds0/2Baths910sqft1990 built

$199,000.00

Condominium Active

1116 BEACHCOMBER COURT UNIT 3 OSPREY, FL 34229

3 Beds1/2Baths2,718sqft2005 built

$545,000.00

Condominium Active

232 WOODLAND DRIVE UNIT 232 OSPREY, FL 34229

2 Beds0/2Baths1,483sqft1980 built

$264,900.00

Single Family Residence Active

125 BURNS ROAD TERRA CEIA, FL 34250

4 Beds0/4Baths4,750sqft2020 built

$1,750,000.00

Manufactured Home Active

234 PALM AIR DRIVE OSPREY, FL 34229

2 Beds0/2Baths1,252sqft1984 built

$120,000.00

Single Family Residence Active

660 OLD BARTOW LAKE WALES ROAD BARTOW, FL 33830

3 Beds0/2Baths3,244sqft2019 built

$889,000.00

Single Family Residence Active

146 4TH AVENUE NE UNIT 600 ST PETERSBURG, FL 33701

5 Beds1/6Baths7,457sqft2015 built

$7,950,000.00

Single Family Residence Active

5811 MARINER STREET TAMPA, FL 33609

5 Beds1/4Baths6,672sqft2017 built

$3,990,000.00

Condominium Active

1140 BEACHCOMBER COURT UNIT 11 OSPREY, FL 34229

3 Beds1/2Baths2,718sqft2005 built

$600,000.00

Single Family Residence Active

186 WINDWARD DRIVE OSPREY, FL 34229

3 Beds0/2Baths3,298sqft1983 built

$649,500.00