186 Windward Drive, Osprey, FL 34229
Local realty services provided by:Gulf Shores Realty ERA Powered
Listed by: brittany coleman, pllc
Office: keller williams on the water s
MLS#:N6142087
Source:MFRMLS
Price summary
- Price:$749,900
- Price per sq. ft.:$227.38
- Monthly HOA dues:$204.33
About this home
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**
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Home facts
- Year built:1983
- Listing ID #:N6142087
- Added:45 day(s) ago
- Updated:February 23, 2026 at 02:17 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:2
- Full bathrooms:2
- Living area:2,505 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central
Structure and exterior
- Roof:Tile
- Year built:1983
- Building area:2,505 sq. ft.
- Lot area:0.3 Acres
Schools
- High school:Venice Senior High
- Middle school:Sarasota Middle
- Elementary school:Laurel Nokomis Elementary
Utilities
- Water:Public, Water Available, Water Connected
- Sewer:Public Sewer, Sewer Available, Sewer Connected
Finances and disclosures
- Price:$749,900
- Price per sq. ft.:$227.38
- Tax amount:$7,566 (2025)
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