Properties

Property Description

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
: Central
: Central Air
: Garden
: Yes
: Covered, Screened, Patio
: Unfurnished
: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
: Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Pool, Sidewalks, Tennis Court(s), Playground, Park, Dock, Intracoastal Waterway, Boat Slip, Marina
: Irrigation System, Rain Gutters, Sliding Doors, Lighting, Private Mailbox
: Hardwood
2
: Living Room/dining Room Combo, Walk-in Closet(s), Split Bedroom, Cathedral Ceiling(s), Kitchen/family Room Combo, Thermostat, Vaulted Ceiling(s), Ceiling Fan(s), Primary Bedroom Main Floor, High Ceilings
: Laundry Room, Inside
: Corner Lot, Landscaped
: Driveway, Garage Door Opener, Off Street, Deeded
: Tile
: Public Sewer
: Electricity Connected, Cable Connected, Cable Available, Sewer Connected, Water Connected, Bb/hs Internet Available, Electricity Available, Sewer Available, Water Available
Address Map
FL
Sarasota
OSPREY
34229
186 WINDWARD DRIVE
1
W83° 30' 49.7''
N27° 10' 45.7''
South
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.
SOUTHBAY YACHT & RACQUET CLUB
MLS Addon
: Park, Playground, Pool, Clubhouse, Fitness Center, Tennis Court(s), Pickleball Court(s), Basketball Court
$613
Quarterly
: Common Area Taxes, Community Pool, Manager, Pool Maintenance, Escrow Reserves Fund, Fidelity Bond
: Block, Stucco
98
Laurel Nokomis Elementary
: Slab
Venice Senior High
: One
281525387
281521326
: Cash, Conventional, Va Loan, Fha
Sarasota Middle
: Street Paved
: No
1
$7,566
2025
: Public
RSF2

Residential For Sale

186 WINDWARD DRIVE, OSPREY, Florida 34229

3 Bedrooms
2 Bathrooms
2,505 Sqft
Visits : 10 in 107 days
$649,500
Listing ID #N6142087
Basic Details
Property Type : Residential
Listing Type : For Sale
Listing ID : N6142087
Status : Active
Brokerage Name : KELLER WILLIAMS ON THE WATER S
Agent Name : Brittany Coleman, PLLC
Bathrooms Total : 2
Price : $649,500
Bedrooms : 3
Rooms : 11
Bathrooms : 2
Square Footage : 2,505 Sqft
Year Built : 1983
Lot Size : 0.30 Acre
Building Area : 3,298 Sqft
Property SubType : Single Family Residence
Agent info
Gulf Sands Realty
Contact Agent

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Gulf Sands Realtors

Steve Foster

Stevefosterhomes14@gmail.com

Magdalena Carr

Mcarr.FloridaHomes@hotmail.com

Kristen Silver

kristengulfsandsrealty@gmail.com

Karen Macdonald

Floridahousedream@gmail.com