186 WINDWARD DRIVE Osprey, FL $ 749,900
186 WINDWARD DRIVE
$ 749,900
Recently Listed
Open House 1/11 1:30pm - 4pm
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186 WINDWARD DRIVE

Osprey, FL, 34229
$ 749,900
Bedrooms3 Baths2.0 Sq 2,505

Monthly Estimate*

$ 4,617

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View a Virtual Tour

Single Family Home for sale in Osprey, FL

for $749,900 with 3 bedrooms and 2 full baths. This 2,505 square foot home was built in 1983 on a lot size of 0.3.

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!

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Open House

1/11/2026 1:30 PM - 4:00 PM
186 WINDWARD DRIVE Osprey, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 749,900

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 7,566

Style

Single Family Residence

Lot Size

0.3

Year Built

1983

Town/City

Osprey

County/Region

Sarasota

MLS | Web ID

N6142087

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Cable Connected Electricity Available Electricity Connected Sewer Available Sewer Connected Water Available Water Connected
Roof Tile
Appliances Dishwasher Dryer Electric Water Heater Microwave Range Refrigerator Washer
Zoning RSF2
HOA Fee 613
Garage Spaces 2
Association Fee Includes Common Area Taxes Community Pool Escrow Reserves Fund Fidelity Bond Manager Pool Maintenance
Patio/Porch Features Covered Patio Screened
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 1983
View Garden
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Boat Slip Dock Intracoastal Waterway Marina Clubhouse Deed Restrictions Fitness Center Golf Carts OK Park Playground Pool Sidewalks Tennis Court(s)
Assoc Fee Paid Per Quarterly
County Sarasota
New Construction false
Property Type Residential
Association Amenities Basketball Court Clubhouse Fitness Center Park Pickleball Court(s) Playground Pool Tennis Court(s)
Attached Garage true
Subdivision Name SOUTHBAY YACHT & RACQUET CLUB
Facing Direction South
Garage Y/N true
Total Rooms 11
Full Baths 2
Status Active
Directions 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.
High School Venice Senior High
City OSPREY
Association Name Judy Brown
Senior Community Y/N false
MLS Area 34229 - Osprey
Lot Size Units Square Feet
Lot Size Square Feet 13130
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Laurel Nokomis Elementary
Land Lease Y/N false
Tax Annual Amount 7566.37
Middle/Junior High School Sarasota Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/bddbff36-4bb9-42eb-8348-a3e149cf10e8?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard https://damon-media-group-llc.aryeo.com/sites/wxxbxxx/unbranded
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 136
Legal Description LOT 136 SOUTHBAY YACHT & RACQUET CLUB
Water Access Type Intracoastal Waterway Marina
Minimum Lease 3 Months
Water Access Y/N true
Monthly HOA Amount 204.33
Additional Rooms Bonus Room Family Room
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities 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)
Flooring Hardwood
Furnished Y/N Unfurnished
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Inside Laundry Room
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Irrigation System Lighting Private Mailbox Rain Gutters Sliding Doors
Vegetation Trees/Landscaped
Parking Features Deeded Driveway Garage Door Opener Off Street
Lot Features Corner Lot Landscaped
Water Source Public
Lot Size Area 13130
Foundation Details Slab
Spa false
Building Area Total 3298
Lot Size Acres 0.3
Road Surface Type Paved Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
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* Excluded Features
List By
Keller Williams On The Water S

Broker

brittanycoleman208@gmail.com

Email

Affordability Calculator

$5,248
Per Month
88%
12%
0%
Monthly Principal & Interest
$4,617
Monthly Property Taxes
$631
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Venice Senior High High School High School
Pricing History
DatePricePrice ChangeDescription
1/9/2026$749,900 Listed Price

Map


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186 WINDWARD DRIVE, Osprey, FL, 34229 is a Single Family Home for sale at $749,900 with 2,505 sqft and a lot size of 0.3. 186 WINDWARD DRIVE has 3 bedrooms, 2.0 baths, and was built in 1983. The property's zip code is 34229 which is in Osprey, FL