ActiveMLS# MFR785007536189 days on market
$1,150,000
$450 / sq ft
3427 WINDING OAKS DR #14
LONGBOAT KEY, FL, 34228
3Bedrooms
3Bathrooms
2,555Sq Ft
1988Year Built
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About This Property

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.

Key Features

  • Built in 1988

Property Details

  • Type: Single Family Home
  • Year Built: 1988
  • Lot Size: 0 sq ft
  • Sq Ft: 2,555
  • Price / Sq Ft: $450
  • HOA: Contact Agent
  • Bedrooms: 3
  • Bathrooms: 3
  • Feature: Built in 1988
  • Status: Active
  • MLS Number: MFR785007536
  • Days on Market: 189
  • Listed By: MLS Listing
  • Zip Code: 34228
Listing information © 2026 Miami MLS. Information deemed reliable but not guaranteed. This listing is represented by TruDeals Realty at 0.5% seller commission. Buyer's agent commission is separate and negotiable.
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$1,150,0003427 WINDING OAKS DR #14, LONGBOAT KEY, FL
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