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$820,000
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Property Description
PRICE IMPROVEMENT! This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast. Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground. Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. You're just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School. Don't miss this opportunity to own a beautiful home in one of the Gulf Coast's most desirable boating communities
Full Property Details
Full Property Details for 123 Windward Dr
General
- Price: $820,000
- HOA FEE: $219/month
- HOA FEE FREQ.: Quarterly
- Taxes: $3,109 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4656319
- Updated: 2/11/2026
- Added to Site: 160 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 9
- Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Window Treatments
- Fireplace: Yes
- Fireplace(s): Family Room, Masonry, Wood Burning
- Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Furnishings: Furnished
- Flooring: Ceramic Tile, Engineered Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room, Washer Hookup
Additional Information
- Shared Amenities: Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Pickleball Court(s), Playground, Pool, Recreation Facilities, Tennis Court(s), Vehicle Restrictions
Exterior
- Exterior Features: French Doors, Garden, Hurricane Shutters, Irrigation System
- Deck/Patio: Covered, Patio, Screened
- Porch/Patio/Deck: Covered, Patio, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
- Driving Directions: From US 41 turn onto Southbay Dr., continue through the community and take a right onto Windward Dr. 123 Windward is on the right. Alternatively, from US 41, turn onto Blackburn Point Road, then turn left onto Southbay Drive, followed by an immediate left onto Windward Drive. 123 Windward is on the right.
- Direction Faces: Northwest
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Laurel Nokomis Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- Community Features: Dock, Intracoastal Waterway, Marina, Association Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, No Truck/RV/Motorcycle Parking, Playground, Pool, Tennis Court(s)
- Optional Amenities: Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Pickleball Court(s), Playground, Pool, Rec
- Association: Yes
- Assoc. Name: Rachelle Freed
- Assoc. Fees Include: Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Recreational Facilities
- Pet Restrictions: Please refer to governing documents for the community's pet policy.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: None
- Utility Description: Cable TV Available, Electricity Connected, Public, Sewer Connected, Sprinkler Meter, Street Lights, Water Connected
Structural Information
- Architectural Info: Florida
- Architectural Style: Florida
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: One
- Square Feet: 1,894
- Sq. Ft. Source: Public Records
- Year Built: 1979
Lot Features
- Property View: Garden, Park/Greenbelt
- Lot Size (Acres): 0.25
- Lot Size (Sq. Ft.): 10,800
- Lot Size: 10800
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
Financial Considerations
- Association Fee: $657
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $3,109
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 118 SOUTHBAY YACHT & RACQUET CLUB
- Flood Zone Info: X
- APN: 157080013
- Property ID: 157080013
Listed by William Raveis Real Estate
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Schools
Schools serving 123 Windward Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 4.7 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.4 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 123 Windward Dr
Date
Details
Price
Change
Source
1/09/2026
Price Reduced
$820,000
-3.53%
MLS
9/24/2025
Listed
$850,000
—
MLS
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 123 Windward Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,772
-11%
$278,568
3%
2024
$3,109
4%
$270,717
3%
2023
$2,996
3%
$262,832
6%
2021
$2,897
-1%
$247,745
-3%
2022
$2,936
1%
$255,177
4%
2021
$2,897
4%
$244,324
2%
2019
$2,792
3%
$238,831
2%
2018
$2,717
1%
$234,378
2%
2017
$2,703
—
$229,557
2%
2016
$2,693
-2%
$224,835
1%
2015
$2,741
—
$223,272
1%
2014
$2,729
4%
$221,500
6%
2013
$2,613
—
$209,909
—
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 123 Windward Dr
123 Windward Drive, Osprey, FL 34229 (MLS# A4656319) is a Single Family property with 3 bedrooms and 2 full bathrooms. 123 Windward Drive is currently listed for $820,000 and was received on September 24, 2025. Want to learn more about 123 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.

