186 Windward Drive Osprey, FL 34229
Pending MLS# N6142087
3 beds 2 baths 2,505 sq ft Single Family
Details for 186 Windward Drive
MLS# N6142087
Description for 186 Windward Drive, Osprey, FL, 34229
Under contract-accepting backup offers. Price was dropped $50,000 on 5/7! Survey and pool quote are available! 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!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**
Listing Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 3
Bathrooms: 2
Lot Size: 0.30 Acres
Square Feet: 2,505 sq ft
Year Built: 1983
Garage: Yes
Stories: 1 Story
Construction: Block,Stucco
Subdivision: Southbay Yacht & Racquet Club
Foundation: Slab
County: Sarasota
School Information
Elementary: Laurel Nokomis Elementary
Middle: Sarasota Middle
High: Venice Senior High
Room Information
Main Floor
Bonus Room: 18.11x35.8
Dining Room: 10.2x10.11
Living Room: 14.1x21.5
Bathroom 2: 5.1x7.1
Bedroom 2: 12.1x11.8
Bedroom 1: 10.11x12.5
Primary Bathroom: 7.4x11.6
Primary Bedroom: 21.11x11.6
Family Room: 11.11x13.8
Dinette: 12.1x11.8
Kitchen: 11.9x12.9
Bathrooms
Full Baths: 2
Additonal Room Information
Laundry: Inside, Laundry Room
Interior Features
Appliances: Electric Water Heater, Washer, Microwave, Range, Refrigerator, Dryer, Dishwasher
Flooring: Wood
Additional Interior Features: Walk-In Closet(s), Ceiling Fan(s), Vaulted Ceiling(s), High Ceilings, Living/Dining Room, Cathedral Ceiling(s), Split Bedrooms, Main Level Primary, Kitchen/Family Room Combo
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Cable Connected,Electricity Available,Electricity Connected,High Speed Internet Available,Sewer Available,Sewer Connected,Water Available,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: driveway, Off Street, Garage, Garage Door Opener, Deeded
Roof: Tile
Pool: Community, Association
Lot View: Garden
Additional Exterior/Lot Features: Rain Gutters, Sprinkler/Irrigation, Lighting, Patio, Covered, Screened, Corner Lot, Landscaped
Community Features
Community Features: Pool, Boat Slip, Tennis Court(s), Playground, Clubhouse, Dock, Sidewalks, Waterfront, Marina, Park, Fitness, Golf Carts OK
Association Amenities: Clubhouse, Pickleball, Park, Pool, Playground, Tennis Court(s), Fitness Center, Basketball Court
HOA Dues Include: Taxes, Association Management, Reserve Fund, Pool(s), Common Areas
Homeowners Association: Yes
HOA Dues: $613 / Quarterly
Driving Directions
From the intersection at US 41 and Laurel Rd take US 41 north. Turn left on Southbay Dr. Turn right on Windward Dr. Property will be on your left. From the intersection at US 41 and Blackburn Point Rd take Blackburn Point Rd west. Turn left on Southbay Dr. Turn left on Windward Dr. Property will be on your left.
Financial Considerations
Terms: Cash,Conventional,FHA,VA Loan
Tax/Property ID: 0157070011
Tax Amount: 7566.37
Tax Year: 2025
A broker reciprocity listing courtesy: KELLER WILLIAMS ON THE WATER S
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Sales History & Tax Summary for 186 Windward Drive
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 186 Windward Drive
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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