3427 Winding Oaks Dr #14, Longboat Key, Florida
List Price: $1,150,000
MLS Number: A4686623

  • Status: Active
  • DOM: 17 days
  • Square Feet: 2555
  • Bedrooms: 3
  • Baths: 3
  • Garage: 2
  • City: LONGBOAT KEY
  • Zip Code: 34228
  • Year Built: 1988
Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota's coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership--ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances--perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area--while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.

Misc Info

Subdivision: Winding Oaks

Annual Taxes: $13,850

Water Front: Lake Front, Pond

Water View: Lake, Pond

Water Access: Lake, Pond

Lot Size: Non-Applicable

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    Home Features

    Appliances: Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator

    Flooring: Luxury Vinyl, Tile

    Fireplace: Gas, Living Room, Wood Burning

    Air Conditioning: Central Air

    Exterior: Awning(s), Lighting, Sliding Doors

    Garage Features: Deeded, Driveway, Garage Door Opener

    Room Dimensions

    Schools

    • Elementary: Southside Elementary
    • Map
    • Walk Score
    • Street View