Winding Oaks Homes with Gated Community - Guard Community Features

Winding Oaks Homes with Gated Community - Guard Community Features

Welcome to Winding Oaks, a picturesque gated community nestled in the serene surroundings of Longboat Key, Florida. This exclusive subdivision offers a unique blend of tranquility and luxury, making it an ideal haven for those seeking a sophisticated lifestyle in one of the most sought-after areas of Sarasota County.

Winding Oaks boasts a collection of stunning homes, each designed with elegance and comfort in mind. The community features beautifully landscaped grounds, providing residents with a sense of privacy and security. As a guard-gated community, Winding Oaks ensures peace of mind, allowing you to enjoy your surroundings without worry.

The homes within Winding Oaks are characterized by their architectural charm and modern amenities. Spacious layouts, gourmet kitchens, and private outdoor spaces create the perfect setting for both relaxation and entertaining. Many properties feature breathtaking views of lush greenery and serene waterways, enhancing the overall appeal of this enchanting neighborhood.

Living in Winding Oaks means embracing a lifestyle filled with outdoor activities and leisure. Residents have access to nearby pristine beaches, golf courses, and nature trails, making it easy to enjoy the natural beauty of Longboat Key. The community is also conveniently located near upscale shopping, fine dining, and vibrant cultural attractions in Sarasota.

Whether you’re looking for a year-round residence or a seasonal retreat, Winding Oaks offers an unparalleled living experience defined by luxury, security, and a strong sense of community. Discover your dream home in this idyllic enclave and immerse yourself in the charm of coastal living.

Newest Winding Oaks Homes with Gated Community - Guard Community Features

$949,000
3 Beds ⋅ 3 Baths ⋅ Winding Oaks SubDv. ⋅ 34228 Zip Code
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