Winding Oaks Real Estate

Winding Oaks Real Estate

Welcome to Winding Oaks, a hidden gem nestled in the picturesque paradise of Longboat Key, Florida. This exclusive subdivision offers a tranquil retreat that perfectly blends the charm of coastal living with the comforts of modern amenities. With its lush landscapes and winding streets, Winding Oaks is a serene community that invites you to unwind and savor the beauty of nature.

Located in Sarasota County, Winding Oaks is just a stone's throw away from the stunning beaches that Longboat Key is renowned for. Residents can enjoy sun-soaked days on the sandy shores, indulge in world-class dining, or explore the vibrant local arts scene. The area is renowned for its stunning sunsets and year-round warm weather, making it an ideal spot for those seeking a laid-back lifestyle.

Within Winding Oaks, you’ll find beautifully designed homes that exude elegance and sophistication. Each property is thoughtfully crafted to provide spacious living areas, gourmet kitchens, and private outdoor spaces, perfect for entertaining or simply enjoying the serene surroundings. The community is characterized by its friendly atmosphere, where neighbors become friends and every day feels like a vacation.

For those who enjoy outdoor activities, Winding Oaks offers easy access to walking trails, golf courses, and water sports. Plus, with nearby shopping centers and cultural attractions, you’ll have everything you need at your fingertips.

Experience the unparalleled lifestyle that Winding Oaks has to offer. Whether you're looking for a permanent residence or a seasonal getaway, this enchanting community is ready to welcome you home. Discover your piece of paradise in Longboat Key today!

Newest Listings in Winding Oaks

$949,000
3 Beds ⋅ 3 Baths ⋅ A4680403 MLS ⋅ 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
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