Winding Oaks Homes with Private Yard Exterior Features

Winding Oaks Homes with Private Yard Exterior Features

Welcome to Winding Oaks, an enchanting subdivision nestled in the heart of Longboat Key, Florida, within picturesque Sarasota County. This hidden gem offers a serene oasis where coastal charm meets modern elegance. With its lush landscapes and tranquil surroundings, Winding Oaks is the perfect haven for families, retirees, and anyone seeking a slice of paradise.

The homes in Winding Oaks are thoughtfully designed to provide comfort and style, featuring exquisite private yards that invite outdoor living at its finest. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by vibrant gardens and the gentle rustle of palm trees. Each residence boasts spacious layouts, allowing for seamless indoor-outdoor living, perfect for entertaining guests or enjoying quiet evenings under the stars.

Residents of Winding Oaks enjoy the best of both worlds—secluded tranquility and close proximity to the stunning beaches of Longboat Key. With easy access to the sparkling Gulf of Mexico, you can indulge in sun-soaked days, beach strolls, and water sports at your leisure. The community is also conveniently located near boutique shops, fine dining, and vibrant cultural attractions, ensuring that everything you need is just a stone's throw away.

Embrace the lifestyle you've always dreamed of in Winding Oaks, where every day feels like a vacation. With its captivating homes and inviting atmosphere, this subdivision offers a unique opportunity to experience the best of Florida living. Come discover your new sanctuary in Winding Oaks—your personal paradise awaits!

Newest Winding Oaks Homes with Private Yard 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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