Winding Oaks Homes with Gated Community - Guard Community Features

Welcome to Winding Oaks, a prestigious subdivision located in the heart of Longboat Key, Sarasota County, Florida. This exclusive community offers a luxurious lifestyle in a serene and secure environment.

Winding Oaks is known for its beautifully landscaped grounds, winding streets, and elegant homes. The neighborhood features a gated entrance with a guard on duty, providing residents with peace of mind and added security.

The homes in Winding Oaks are designed with the highest standards of quality and craftsmanship. From spacious single-family homes to elegant villas, there is a wide range of housing options to suit every taste and lifestyle. Many of the properties boast stunning views of the surrounding natural beauty, including lush greenery and tranquil water features.

Residents of Winding Oaks enjoy access to a variety of amenities, including a community pool, tennis courts, and walking trails. The subdivision is conveniently located near Longboat Key's pristine beaches, world-class golf courses, upscale shopping, and fine dining establishments.

Whether you are looking for a permanent residence or a vacation home, Winding Oaks offers the perfect blend of luxury, comfort, and convenience. Come and experience the beauty and elegance of Winding Oaks – where every day feels like a retreat.

Newest Winding Oaks Homes with Gated Community - Guard Community Features

$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

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