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$749,900
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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!
Full Property Details
Full Property Details for 186 Windward Dr
General
- Price: $749,900
- HOA FEE: $204/month
- HOA FEE FREQ.: Quarterly
- Taxes: $7,566 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: N6142087
- Updated: 1/11/2026
- Added to Site: 8 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 11
- Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Exterior
- Exterior Features: Irrigation System, Lighting, Private Mailbox, Rain Gutters, Sliding Doors
- Deck/Patio: Covered, Patio, Screened
- Porch/Patio/Deck: Covered, Patio, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Deeded, Driveway, Garage Door Opener, Off Street
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
- Driving 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.
- Direction Faces: South
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Sarasota Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Community Features: Boat Slip, Dock, Intracoastal Waterway, Marina, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
- Optional Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
- Association: Yes
- Assoc. Name: Judy Brown
- Assoc. Fees Include: Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Pool Maintenance
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: One
- Square Feet: 2,505
- Sq. Ft. Source: Public Records
- Year Built: 1983
Lot Features
- Property View: Garden
- Lot Size (Acres): 0.3
- Lot Size (Sq. Ft.): 13,130
- Lot Size: 13130
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Water Features
- Water Access: Yes
- Water Access Desc: Intracoastal Waterway, Marina
Financial Considerations
- Association Fee: $613
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $7,566.37
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 136 SOUTHBAY YACHT & RACQUET CLUB
- Flood Zone Info: X
- APN: 157070011
- Property ID: 157070011
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Schools
Schools serving 186 Windward Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 4.8 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.5 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 186 Windward Dr
Date
Details
Price
Change
Source
1/08/2026
Listed
$749,900
29.29%
MLS
10/08/2021
Sold
$580,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 186 Windward Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,756
-19%
$588,800
-14%
2024
$8,291
9%
$685,700
10%
2023
$7,601
133%
$624,500
125%
2021
$3,266
-51%
$278,153
-48%
2022
$6,666
104%
$539,700
97%
2021
$3,266
4%
$274,313
2%
2019
$3,155
3%
$268,146
2%
2018
$3,075
1%
$263,146
2%
2017
$3,059
—
$257,734
2%
2016
$3,049
-2%
$252,433
1%
2015
$3,104
—
$250,678
1%
2014
$3,091
—
$248,688
1%
2013
$3,088
—
$245,013
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 186 Windward Dr
186 Windward Drive, Osprey, FL 34229 (MLS# N6142087) is a Single Family property with 3 bedrooms and 2 full bathrooms. 186 Windward Drive is currently listed for $749,900 and was received on January 08, 2026. Want to learn more about 186 Windward Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

