Winding Oaks

3444 Winding Oaks Dr Longboat-large-002-10-002-1500x1000-72dpi


Under Contract. Welcome home to this maintenance free villa that lives like a single-family home within the coveted enclave of Winding Oaks behind the gates of the Longboat Key Club. This residence is situated on a pie shaped lot offering an expansive front landscaped area unique to any other in the community. You are immediately greeted by an attractive loggia leading to the glass front entry door. A sense of grandeur is felt once inside due to the profusion of light through the walls of glass and vaulted ceilings. The spacious living room offers a fireplace, custom cabinetry and peaceful lagoon views. Outdoors you will find an expansive deck accessible from the living room and master suite which provides the perfect atmosphere of serenity to enjoy morning coffee, alfresco dining or simply bask in the radiant sun. The spacious master suite boasts multiple customized closets and a luxurious bath. The split plan floor plan has a separate guest wing with access to a well-designed laundry room. The kitchen features newer appliances, abundant counter space, a dedicated pantry and opens to the family room offering a built-in desk and access to the garden.  Buyers will be impressed by this pet friendly environment and over $3Million Dollars in capital improvements (newer pool, roofs, paver drives, mailboxes, painting and more), along with membership to the exclusive Bay Isles Beach Club.

Floor Plan

Winding Oaks Community Information

Winding Oaks is one of 16 residential communities located within Bay Isles, a planned and gated development in the center of Longboat Key, an 11-mile long barrier island just west of Sarasota, between the Gulf of Mexico and Sarasota Bay.

The neighborhood is comprised of 56 maintenance-free Nantucket-style 2 and 3 bedroom homes, surrounded by the Longboat Key Club Golf Course and a sparkling inland waterway.

Over the past several years, existing homeowners have invested nearly $3 million in major capital improvements to completely transform the community. Upgrades include:

  • New state-of-the-art 24 x 55′ infinity swimming pool
  • New community wide landscaping outside the walls of each unit 
  • New tile roofs on every unit
  • New paver drives and walkways
  • Complete exterior painting and replacement of much of the siding and trim with durable Azek products
  • Renovated and upgraded sprinkler system
  • New mailboxes
  • New signage and landscaping at both entrances

All of the renovations have been funded by the current owners so new owners don’t need to worry. The neighborhood is managed by a hands-on Homeowners Association and Board of Directors, who have made sure that things are done right and that there are reserves for future improvements.

Winding Oaks’ town homes live like single family homes. They are all on one-level and every home has pond or lagoon view, a two-car garage, private courtyard, private deck and some have private pools and spas. Residents enjoy the beauty, security and benefits of Bay Isles, including access to the Bay Isles Beach Club on Gulf of Mexico Drive.

One of the most popular aspects of Winding Oaks is that, unlike a lot of LBK associations, it is completely pet-friendly with many residents owning dogs of all sizes.

Residents include people of all ages from all over the world, some part-time, some full-time. There are a number of neighborhood social activities including parties, book and card clubs and several committee opportunities.

Property Details

Contact Addy-Wittig
  • Listing Price: $575,000
  • Address: 3444 Winding Oaks Drive
  • City: Longboat Key
  • State: FL
  • Zip: 34228
  • MLS #: A4207351
  • Square Feet: 2,189
  • Bedrooms: 2
  • Bathrooms: 2
  • Virtual Tour