186 Windward Drive, OSPREY, FL

$649,500

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3

Beds

2

Baths

2,505

Square feet

0.30

Acres

About 186 Windward Drive

Price was reduced over $100,000!!! Went pending immediately and then the buyers couldn't secure financing. It is now BACK ON MARKET as of 3/19 and NO INSPECTIONS HAVE BEEN DONE! 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.**

Features of 186 Windward Drive

MLS® # N6142087
Price $649,500
Bedrooms 3
Bathrooms 2.00
Full Baths 2
Square Footage 2,505
Acres 0.30
Year Built 1983
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 186 Windward Drive
Area Osprey
Subdivision SOUTHBAY YACHT & RACQUET CLUB
City OSPREY
County Sarasota
State FL
Zip Code 34229-9751

Amenities

Amenities Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Parking Deeded, Driveway, Garage Door Opener, Off Street
# of Garages 2
View Garden
Is Waterfront No
Has Pool No

Interior

Interior Features Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
Appliances Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Heating Central
Cooling Central Air
Fireplace No
# of Stories 1

Exterior

Exterior Features Irrigation System, Lighting, Private Mailbox, Rain Gutters, Sliding Doors
Lot Description Corner Lot, Landscaped
Roof Tile
Foundation Slab

School Information

Elementary Laurel Nokomis Elementary
Middle Sarasota Middle
High Venice Senior High

Additional Information

Date Listed January 8th, 2026
Days on Market 85
Zoning RSF2
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeKELLER WILLIAMS ON THE WATER S

Listing Map

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