Winding Oaks Homes with Deed Restrictions Community Features

Winding Oaks Homes with Deed Restrictions Community Features

Welcome to Winding Oaks, a charming subdivision nestled within the serene city of Longboat Key, Sarasota County, Florida. This exclusive community offers a unique blend of luxury living and natural beauty, making it a sought-after destination for homebuyers seeking a tranquil retreat.

Winding Oaks is a Homes with Deed Restrictions community, ensuring that the neighborhood maintains its pristine appearance and high property values. Residents can enjoy peace of mind knowing that the community's aesthetic appeal is preserved through these restrictions.

True to its name, Winding Oaks is characterized by its lush oak trees and winding streets, creating a picturesque setting for residents to call home. The neighborhood boasts well-manicured landscapes and a sense of privacy, providing a peaceful oasis for those looking to escape the hustle and bustle of city life.

In addition to its natural beauty, Winding Oaks offers a range of community features for residents to enjoy. From private walking trails to recreational facilities, there are plenty of opportunities for outdoor activities and socializing with neighbors.

Whether you're looking for a full-time residence or a vacation home, Winding Oaks offers a unique living experience that combines luxury, tranquility, and community spirit. Come and discover the beauty of Winding Oaks – where every day feels like a retreat.

Newest Winding Oaks Homes with Deed Restrictions 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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