186 WINDWARD DRIVE, Osprey, FL 34229

• 3 beds |
• 2 baths |
• 2,505 sqft

Property Description

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.**

Listing Status:

Active

Date Added:

January 8, 2026

Data Last Updated:

February 10, 2026 at 5:22PM

Listing Office:

KELLER WILLIAMS ON THE WATER S : 941-803-7522

Listing Agent:

Brittany Coleman, PLLC : 941-539-5023

MLS ID:

N6142087

Interior

• General: Cathedral Ceiling(s)Ceiling Fans(s)High CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorSplit BedroomThermostatVaulted Ceiling(s)Walk-In Closet(s)
• Rooms: Bonus RoomFamily Room
• Appliances: DishwasherDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: Wood
• A/C: Central Air
• Heating: Central

Exterior

• General: LightingPrivate MailboxRain GuttersSliding Doors
• Other Structures: ScreenedPatioCovered
• Parking: DeededDrivewayGarage Door OpenerOff Street

Construction

• Roofing: Tile
• General: BlockStuccoOneSlab

Location

• Road/Access: Asphalt
• HOA Amenities: Basketball CourtClubhouseFitness CenterParkPickleball Court(s)PlaygroundPoolTennis Court(s)Common Area TaxesPoolEscrow Reserves FundFidelity BondManagement613.0Quarterly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RSF2LOT 136 SOUTHBAY YACHT & RACQUET CLUB0157070011
• View: Garden

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableCable ConnectedElectricity AvailableElectricity ConnectedSewer AvailableSewer ConnectedWater AvailableWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple