Winding Oaks Homes with Beach View Water Frontage

Welcome to Winding Oaks, a hidden gem nestled in the picturesque surroundings of Longboat Key, Florida. This exclusive subdivision offers the perfect blend of luxury living and coastal charm, making it an ideal destination for those seeking a serene lifestyle by the water. With its lush landscaping and beautifully designed homes, Winding Oaks is a community that truly embodies the essence of Florida living.

One of the standout features of this enchanting neighborhood is its stunning beach view waterfront homes. Imagine waking up to the gentle sound of waves lapping at the shore and basking in the warm Florida sun from the comfort of your own backyard. Each residence in Winding Oaks is thoughtfully designed to maximize the breathtaking views of the Gulf of Mexico, allowing you to enjoy the beauty of nature right outside your window.

The homes in Winding Oaks boast a variety of architectural styles, from modern coastal designs to classic Floridian aesthetics. Spacious layouts, high-end finishes, and expansive outdoor living areas make these homes perfect for entertaining family and friends or simply enjoying a peaceful evening while watching the sunset over the water.

Residents of Winding Oaks also benefit from easy access to the pristine beaches of Longboat Key, where you can indulge in sunbathing, swimming, and beachcombing. With nearby shopping, dining, and recreational activities, this subdivision offers the perfect balance of relaxation and adventure.

Discover the allure of Winding Oaks, where your dream waterfront lifestyle awaits!

Newest Winding Oaks Homes with Beach View Water Frontage

$949,000

3 Beds ⋅ 3 Baths ⋅ Winding Oaks SubDv. ⋅ 34228 Zip Code ⋅ A4680403 MLS ⋅ Active Status ⋅ 18 BLDG.

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.

3435 Winding Oaks Drive Unit 18, Longboat Key

Start Your Search

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by San Diego MLS®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2026 San Diego MLS®,