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Property for sale at 102 WINDWARD DRIVE, OSPREY, FL, 34229
Property for sale at 102 WINDWARD DRIVE, OSPREY, FL, 34229
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102 Windward DriveOsprey, FL, 34229

3beds
3baths
2,134sqft
Single Family Residence
Built in 1986
$657 Quarterly HOA Fee
$1,047,000
For sale
Price per sqft
$491
Days on market
28
Listed
Oct 10
MLS #TB8556740Updated Oct 11, 2026

About this property

Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival.

Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry.

The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access.

Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience.

Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain.

Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

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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
Building stories
1
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 2:45 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

Property for sale at 102 WINDWARD DRIVE, OSPREY, FL, 34229
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