Under contract-accepting backup offers. Privately tucked away

swipe instructions
Tap to see more photos

Condo Sale Pending

3427 WINDING OAKS DR 14

Longboat Key, Florida 34228

Sarasota County

Waterfront: Yes

Community: WINDING OAKS

map
$1,150,000 3 br, 3.0 bath 2555 sq. ft. 0.000 acres

Under contract-accepting backup offers. 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.

Interior:
  • Bedrooms: 3
  • Baths: 3.0
  • Sq Ft: 2555
  • Year Built: 1988
  • Utilities: 
  • Fireplaces: Has Fireplace
  • Stories: 
  • Heat/AC: Central, Electric (Heating), Fireplace(s), Natural Gas
  • Garage: Driveway, Garage, Garage - Attached
Exterior:
  • Lot Size: 0.000 acre
  • Lot Dimensions: 
  • Waterfront: Yes
  • View Types: 
  • Yard: 
  • Siding: HardiPlank Type
  • Roof: Tile
  • Property Taxes: $13,850
  • Swimming Pool: Yes
  • MLS #: A4686623
  • Unit Number: 14
Get More Info
static map
Contact Information:
Beach Condo Sale Pending in Longboat Key, Florida
Listing Agent: Carolyn Donnelly, PA, Coldwell Banker, 941-350-9900, 941-383-6411 Listing Site, Listing Status: Pending
Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Ad Number: 7459155
Viewed 50 times.
Updated: Mar 24, 2026

This property is a Condo located at 3427 WINDING OAKS DR 14, Longboat Key, Florida 34228, and is currently Sale Pending at $1,150,000. This Condo has 3 bedrooms, 3.0 baths, 2555 sq ft.