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3427 WINDING OAKS DR #14,  LONGBOAT KEY, FL 34228

MLS# A4686623.  3 beds.  3.0 baths.  Condo.  Active

$13,850 in taxes (2025)

$1,150,000

 

Remarks:

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.

Quick Info:

  • Listing is courtesy Of: COLDWELL BANKER REALTY ((941-383-6411))
  • Listing Agent: Carolyn Donnelly, Pa ((941-350-9900))
  • Days on yellowkey: 13
  • Property Type: Condo
  • Beds: 3
  • Baths: 3.0
  • Living Area Square Feet: 2555
  • Built 1988
  • Taxes: $13,850 (2025)
  • Garage Spaces: ()
  • Square Feet: 3270
  • Fees: $0 Quarterly
  • Sarasota County
  • Terms: Cash, Conventional, VA Loan
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  • Occupancy Information: Vacant
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  • Subdivision Name: WINDING OAKS
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History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
3/23/2026Sale13A4686623listed for sale$1,150,000-351.6819MLS




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