New Listing - 01/08/2026

$749,900 ($299.36 per sqft)

Est. Mortgage $3,597/mo *

Quick Pre-Approval

Open House Schedule

01/11/2026
1:30 PM to 4:00 PM
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186 WINDWARD DRIVE, Osprey, FL, 34229

186 WINDWARD DRIVE, Osprey, FL, 34229

11 rooms

3 beds

2 Full baths

1983

2,505 sqft

Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, 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. 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!


Status:

Active

Type:

Single-family residential

Furnished Remarks:

Unfurnished

Laundry Remarks:

Inside, Laundry Room

Subdivision:

SOUTHBAY YACHT & RACQUET CLUB

Garage:

2-car Deeded, Driveway, Garage Door Opener, Off Street

Heating:

Central

Cooling:

Central Air

Levels:

1

Common Charge:

$613 Quarterly

Acreage:

0.3

Est. Taxes:

$7,566

HOA Fee

$613

Construction

Block, Stucco

Utilities

BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected

Lot Description:

Corner Lot, Landscaped

View Description:

Garden

Amenities:

Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)

Elementary School:

Laurel Nokomis Elementary

Middle School:

Sarasota Middle

High School:

Venice Senior High

Days on Market:

1

Pet Policy:

Yes

Appliances:

Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer

Min Lease Term:

3 Months

MLS #:

N6142087


Community Info

School Info

Walk Score

Yelp



Listing courtesy of KELLER WILLIAMS ON THE WATER S 941-803-7522