Back 186 Windward Drive
Off Market

186 Windward Drive

Osprey FL 34229

3
2
2
3298 sq. ft.
13130 sq. ft.
Single-Family
Last sold for $565,000
Brittany ColemanBrittany Coleman, last sold this property on 20 July 2026 after 192 days on market.

Overview

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.**

Features

3 bedrooms
2 bathrooms
2 carspaces
2 garage spaces
3298 sq. ft. floor area
13130 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Osprey over the last 12 months, the estimated median property value of 186 Windward Drive is $662.5k.

Median value
$662.5k
Estimated value range
$200k - $4.04m
Median days on market
32
Estimated value trend
-15%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Osprey. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 186 Windward Drive

2026
Sold
$565,000
20 Jul 2026 by Brittany Coleman, of KELLER WILLIAMS ON THE WATER S

Happy sellers in Osprey

66%
66% of sellers in Osprey reported that their sale price either exceeded or met their price expectations.

Osprey stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 11 reviews in Osprey over the last 12 months.

Local market activity for 3 bedroom single-family properties in Osprey

In the last 12 months, 69 three-bedroom single-family properties similar to 186 Windward Drive, have been sold.

This represents a 16% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

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