Date
Details
Price
Change
Source
11/19/2025
Listed
$800,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/78
$800,000
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Property Description
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.
Full Property Details
Full Property Details for 102 Windward Dr
General
- Price: $800,000
- HOA FEE: $219/month
- HOA FEE FREQ.: Quarterly
- Taxes: $3,540 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4671793
- Updated: 1/13/2026
- Added to Site: 58 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 9
- 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
- Appliances: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile, Vinyl
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Electric Dryer Hookup, Inside, Washer Hookup
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Deck, Gunite, In Ground, Lighting, Outside Bath Access, Screen Enclosure
Exterior
- Exterior Features: Irrigation System, Lighting, Outdoor Shower, Rain Gutters, Sliding Doors, Sprinkler Metered
- Deck/Patio: Covered, Deck, Patio, Screened
- Porch/Patio/Deck: Covered, Deck, Patio, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener, Ground Level, Off Street, Oversized
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
- Driving Directions: U.S. 41 to Blackburn Point Road in Osprey, left onto Southbay Drive and immediate left onto Windward Drive. 102 Windward will be on the left.
- Direction Faces: East
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Laurel Nokomis Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- 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)
- Association: Yes
- Assoc. Name: Judy Brown
- Assoc. Fees Include: Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Recreational Facilities
- Pet Restrictions: Please refer to governing documents for the association's pet policy.
- Management Type: On Site Property Manager
- Mgmt. Company: On Site Property Manager
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected, Sewer Connected, Sprinkler Meter, Water Connected
Structural Information
- Architectural Info: Florida
- Architectural Style: Florida
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: One
- Square Feet: 2,134
- Sq. Ft. Source: Public Records
- Year Built: 1986
Lot Features
- Lot Size (Acres): 0.36
- Lot Size (Sq. Ft.): 15,778
- Lot Size: 15778
- Street/Road Desc.: Asphalt
Water Features
- Water Front Desc.: Waterfront
Financial Considerations
- Association Fee: $657
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $3,540
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 129 SOUTHBAY YACHT & RACQUET CLUB
- Flood Zone Info: X
- APN: 157080006
- Property ID: 157080006
Listed by William Raveis Real Estate
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Listing agents
— 102 Windward Dr —
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Schools
Schools serving 102 Windward Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 4.7 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 102 Windward Dr
Tax History
Tax History for 102 Windward Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,203
261%
$316,155
3%
2024
$888
5%
$307,245
3%
2023
$845
4%
$298,296
6%
2021
$814
1%
$281,173
-3%
2022
$809
-1%
$289,608
4%
2021
$814
-75%
$277,291
2%
2019
$3,253
3%
$271,057
2%
2018
$3,172
1%
$266,003
2%
2017
$3,156
—
$260,532
2%
2016
$3,146
-2%
$255,173
1%
2015
$3,202
—
$253,399
1%
2014
$3,188
—
$251,388
1%
2013
$3,185
—
$247,673
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 102 Windward Dr
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102 Windward Drive, Osprey, FL 34229 (MLS# A4671793) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 102 Windward Drive is currently listed for $800,000 and was received on November 19, 2025. Want to learn more about 102 Windward Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.