$650,000
102 Windward Drive
Osprey, FL 34229
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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.
Local Insight
At $305/sqft in Southbay Yacht & Racquet Club, you're paying a solid premium for the amenities and community access rather than the home itself—the 1986 construction means you should budget for potential updates to systems and finishes, though being in flood zone X removes that insurance cost burden. The private pool and relatively modest $219 monthly HOA are genuine draws for the price point, but verify what club amenities (dock access, tennis, etc.) actually come with your membership, as that's what justifies the premium over comparable Osprey homes without the association fees. The 0.36-acre lot is tight for the area, so proximity to neighbors is real—take the 360° tour seriously and drive the neighborhood at different times to assess whether the waterfront lifestyle trade-offs feel right for $650k.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history169 days on market
- Status: SoldJun 4, 2026
- Listed$800,000Nov 19, 2025
- Price reduced$650,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Sold
- Days on market
- 169
- Subdivision
- Southbay Yacht & Racquet Club
- County
- Sarasota
- Year built
- 1986
- Living area
- 2,134 sq ft
- Price/sq ft
- $305
- Building area
- 3,000 sq ft (Public Records)
- Lot size
- 15,778 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12115C0236G)
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $3,540 (2024)
- Parcel #
- 0157080006
- Zoning
- RSF2
- MLS #
- A4671793
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Carpet, Ceramic Tile, Vinyl
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Interior features
- Cathedral Ceiling(s), Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Window Treatments
- Laundry
- Electric Dryer Hookup, Inside, Washer Hookup
- Stories / Levels
- One
- Direction faces
- East
Heating & Cooling
- Heating
- Central, Electric
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener, Ground Level, Off Street, Oversized
HOA & Financial
- HOA fee
- $657 / Quarterly
- Monthly HOA
- $219/mo
- Total monthly fees
- $219/mo
- Total annual fees
- $2,626
- HOA name
- Rachelle Freed
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 3 Months
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Please refer to governing documents for the association's leasing policy.
Exterior & Construction
- Exterior features
- Lighting, Outdoor Shower, Rain Gutters, Sliding Doors, Sprinkler Metered
- Construction materials
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Sewer Connected, Sprinkler Meter, Water Connected
Community
- Pets allowed
- Cats OK, Dogs OK
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | 14x15 |
| Dinette | First | 9x10 |
| Kitchen | First | 11x11 |
| Laundry | First | 6x10 |
| Primary Bedroom | First | 13x16 |
| Bedroom 3 | First | 13x12 |
| Balcony/Porch/Lanai | First | 36x8 |
| Great Room | First | 23x19 |
| Dining Room | First | 11x13 |
Listing Details
- Listing date
- 2025-11-19
- On market date
- 2025-11-19
- Original list price
- $800,000
- Occupant type
- Vacant
- MLS area
- 34229 - Osprey
- Listing AOR
- Sarasota - Manatee
- Status changed
- 2026-06-04
- Tax legal description
- LOT 129 SOUTHBAY YACHT & RACQUET CLUB
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
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.
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 4, 2026 at 3:59 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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