Winding Oaks Homes with Courtyard Exterior Features

Winding Oaks Homes with Courtyard Exterior Features

Welcome to Winding Oaks, a hidden gem nestled in the picturesque Longboat Key, Florida. This exclusive subdivision offers a rare blend of coastal charm and sophisticated living, making it the perfect sanctuary for those seeking a tranquil yet vibrant lifestyle. With its lush landscapes and serene surroundings, Winding Oaks is an idyllic retreat for families and retirees alike.

One of the standout features of homes in Winding Oaks is their stunning courtyard exterior designs. These thoughtfully crafted homes boast private courtyards that serve as an extension of your living space, offering a secluded oasis for relaxation and entertainment. Imagine sipping your morning coffee surrounded by fragrant blooms and the gentle sound of rustling palm fronds, or hosting evening gatherings under the stars in your own intimate setting. The courtyard layouts not only enhance the aesthetic appeal of the homes but also provide a perfect blend of privacy and community.

Residents of Winding Oaks enjoy convenient access to the beautiful beaches of Longboat Key, where sun-soaked days can be spent basking in the warm Florida sun or indulging in water sports. The area is also home to a variety of upscale dining options, boutique shopping, and recreational activities, ensuring that there's always something to do just moments from your doorstep.

With a commitment to quality and luxury, Winding Oaks offers an unparalleled lifestyle in one of Florida's most desirable locations. Come explore the charm of this exquisite neighborhood and discover your dream home today!

Newest Winding Oaks Homes with Courtyard Exterior 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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