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.
| Price | $750,000 | |
| Bedrooms | 3 | |
| Full Baths | 2 | |
| Half Baths | 1 | |
| Total Baths | 3 | |
| Property Style | Florida | |
| Lot Size Area | 15778 | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.36 | |
| Property Type | Residential | |
| Sub type | Single Family Residence | |
| MLS Sub type | Single Family Residence | |
| Features | Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Window Treatments | |
| Exterior Features | Irrigation System, Lighting, Outdoor Shower, Rain Gutters, Sliding Doors, Sprinkler Metered | |
| Year Built | 1986 | |
| Subdivision | SOUTHBAY YACHT & RACQUET CLUB | |
| Roof | Tile | |
| Heating | Central, Electric | |
| Foundation | Slab | |
| Lot Description | Cleared | |
| Laundry Features | Electric Dryer Hookup, Inside, Washer Hookup | |
| Pool features | Deck, Gunite, In Ground, Lighting, Outside Bath Access, Screen Enclosure | |
| Parking Description | Driveway, Garage Door Opener, Ground Level, Off Street, Oversized | |
| Garage spaces | 2 | |
| Association Name | Rachelle Freed | |
| Association Fee | 656 | |
| 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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| County | Sarasota | |
| Latitude | 27.179328 | |
| Longitude | -82.484207 | |
| Market Area | 34229 – Osprey | |
| Address | 102 WINDWARD DRIVE, OSPREY, FL 34229 | |
| Postal Code | 34229 | |
| City | OSPREY | |
| State | FL | |
| Country | United States | |
| Listing Office | WILLIAM RAVEIS REAL ESTATE | |
| Listing Office Phone | 941-867-3901 | |
| Listing Agent | David Cyr | |
| Listing Agent Phone | 941-400-4691 | |
| Virtual Tour U R L Unbranded2 | https://www.zillow.com/view-imx/361d6d1f-41af-4352-bb1e-171522def35e?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard | |
| Compensation Disclaimer | The offer of compensation is made only to participants of the MLS where the listing is filed. | |
| Special listing conditions | None | |
| Ownership | Fee Simple | |
| Virtual Tour URL | https://www.propertypanorama.com/instaview/stellar/A4671793 | |
| Elementary School | Laurel Nokomis Elementary | |
| Middle School | Laurel Nokomis Middle | |
| High School | Venice Senior High | |
| Days on market | 105 | |
| MLS Status | Active | |
| Listing Date | Nov 19, 2025 | |
| Listing Last Modified | Mar 4, 2026 | |
| Tax ID | 0157080006 | |
| Tax Year | 2024 | |
| Tax Annual Amount | 3540 | |
| MLS Area | 34229 – Osprey | |
| MLS # | A4671793 | |
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