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.
Listed By
Agency Name: COLDWELL BANKER REALTY
Agency Contact: 941-383-6411
Shown By
Agent Name: Cheryl Dziurzynski
Agent Phone: (904) 377-6986
Agency Title: Watson Realty Corp., REALTORS ®
Estimated Payment
$ 7,034.97 per month $5,545.47 Principal & Interest $1,154.08 Property Tax $335.42 Homeowner's InsuranceSend an email with a link to
3427 Winding Oaks Drive, Unit 14, Longboat Key, FL 34228.
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3427 Winding Oaks Drive, Unit 14, Longboat Key, FL 34228.
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3427 Winding Oaks Drive, Unit 14 | MLS# A4686623
This condo located at 3427 Winding Oaks Drive, Unit 14, Longboat Key, FL 34228 is currently listed for sale with an asking price of $1,150,000. This property was built in 1988 and has 3 bedrooms and 3 full baths with 2555 sq. ft. Winding Oaks Drive, Unit 14 is located in the WINDING OAKS subdivision. Search WINDING OAKS real estate on cheryld.watsonrealtycorp.com today.