$800,000
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102 Windward Drive, Osprey, FL 34229

3 Beds
3 Baths
2,134 Sq Ft
Sun, 11/30
12 PM - 2 PM

Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking.Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marinawith residents-only boat slipsprovides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.

  • MLS# A4671793
  • Date Listed11/19/2025
  • Days on Realty 7 Days
  • Bedrooms 3
  • Bathrooms 2 Full baths, 1 Half baths
  • Lot Size 0.36 acres (15,778 sq. ft)
  • Sewer Public Sewer
  • Subdivision SOUTHBAY YACHT & RACQUET CLUB
  • Property Type Single Family
  • County Sarasota
  • Year Built 1986
  • Water Public
  • Square Feet 2,134 sq. ft
  • Price Per Sq. Ft $374.88

Interior Features

  • Appliances Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Flooring Carpet, Ceramic Tile, Vinyl
  • Cooling Central Air
  • Heating Central, Electric

Exterior / Lot Features

  • Exterior Lighting, Outdoor Shower, Rain Gutters
  • Roof Tile
  • Lot Size Acres 0.36
  • Lot Size SQFT 15,778.00
  • Lot Features Cleared

Financial Considerations

  • HOA Fee $600 Quarterly
  • Tax Amount $3,540
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in FL / 34229

Source: Walkscore

41/100

Car-Dependent

Walk Score ®

36/100

Bikable

Bike Score ®

Overview

Most errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 10/100, Transit Score: 0/100, Bike Score: 34/100.

Property Change History

Property description updated with new details
Property description updated with new details

Points of Interest near 102 WINDWARD DRIVE, OSPREY, FL 34229

Frequently Asked Questions for 102 WINDWARD DRIVE

Source: Realty.com

102 WINDWARD DRIVE, OSPREY, FL 34229 is a Single Family 2,134 sq. ft. home listed for sale. Realty.com has 78 photos available of this 3 bed, 3 bath house, listed at $800,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 78 photos of 102 WINDWARD DRIVE.

Our records indicate that 102 WINDWARD DRIVE was built in 1986.

The full address for this home is 102 WINDWARD DRIVE, OSPREY, FL 34229.

102 WINDWARD DRIVE has been listed on Realty.com since Wed November 19, 2025

Most errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 10/100, Transit Score: 0/100, Bike Score: 34/100.

There are 3 schools assigned to this home. Check out the schools near 102 WINDWARD DRIVE. Island Village Montessori School (Grades: PK - 8), Laurel Nokomis Middle (Grades: 6 - 8), Venice Senior High (Grades: 9 - 12)

Listing provided courtesy of: William Raveis Real Estate (tel: 941-867-3901)
Listing agent: David Cyr (#281524403)

This content last refreshed on 2025-11-26 20:27:12. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 102 WINDWARD DRIVE, OSPREY, FL 34229 : MLS# A4671793