Winding Oaks Real Estate

Winding Oaks Real Estate

Welcome to Winding Oaks, a hidden gem nestled in the picturesque Longboat Key, Florida. This enchanting subdivision offers an idyllic blend of tranquility and luxury, making it the perfect retreat for those seeking a serene coastal lifestyle.

Winding Oaks is characterized by its lush, mature landscaping and winding tree-lined streets that create a sense of privacy and exclusivity. The community features elegantly designed homes, many of which boast stunning views of the surrounding natural beauty. With a variety of architectural styles, residents enjoy a unique charm that reflects the essence of coastal living.

Located in Sarasota County, Winding Oaks is just moments away from the pristine beaches of Longboat Key, where soft sands and crystal-clear waters await. Whether you’re enjoying a peaceful sunrise walk along the shore or indulging in a sunset picnic, the beach is an integral part of the Winding Oaks lifestyle.

For those who appreciate the finer things in life, the area is home to upscale dining, boutique shopping, and world-class golf courses. The vibrant cultural scene of Sarasota, with its art galleries, theaters, and museums, is also just a short drive away, providing endless opportunities for entertainment and enrichment.

Winding Oaks is not just a place to live; it’s a community where neighbors become friends and memories are made. Whether you're looking to retire in paradise or raise a family in a safe and welcoming environment, Winding Oaks offers the perfect backdrop for your new chapter. Experience the charm and elegance of this exceptional subdivision, where coastal living meets community spirit.

Newest Listings in Winding Oaks

$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
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