Winding Oaks

Winding Oaks is a neighborhood of duplex condominiums tucked on 14.5 acres in one of the coziest locations in Bay Isles, a master-planned gated development of 16 residential communities. The neighborhood’s prime site sprawls within the scenic Harbourside section of the Bay Isles, just across the equally fascinating single-family homes of Sabal Cove.  

Winding Oaks’ development started in the late 1980s and wound up in early 1990. The neighborhood’s quiet, horseshoe-shaped semicircle perimeter came out quite appealing with its lush tropical landscaping. Besides its trademark oak trees, the community mature palms and shrubbery flourish within this neighborhood.

In any direction, the views in Winding Oaks are simply spectacular. A serene inland waterway embraces the entire Winding Oaks neighborhood, while the well-manicured greens and fairways of the Longboat Key Resort Club’s golf links dominate its outer perimeter.

Million-dollar Neighborhood Updates

Prospective buyers of Winding Oaks residences for sale will likewise be delighted to note the upgrades worth nearly $3 million have been undertaken after the community’s build-out in early 1990. The major improvements included the construction of a new infinity pool and a complete revamp of the neighborhood’s landscaping.

The sprinkler system was also renovated and upgraded, along with the construction of new walkways and paver drives. The makeover likewise covered the installation of new mailboxes, new landscaping and signage at Winding Oaks’ two entrances.

The exterior of the residences were repainted, and much of their trim and siding were replaced. In addition, new tile roofs were installed on every Winding Oaks residence.

Single-family Home Feel

A pet-friendly neighborhood, Winding Oaks was developed with 56 units in 28 duplex houses, with selections of 32 three-bedroom and 24 two-bedroom units. Designed Nantucket-style, these residences feature floor plans ranging from over 2,000 to almost 2,700 square feet.

All were built as one-level residences, which have the feel of single family homes. Each has a lagoon or pond view, private deck, private courtyard and a two-car garage. Choice residences have private pools and spas. 

Delightful Leisure Opportunities

An active, hands-on homeowners association and board of directors manage Winding Oaks. The residents of Winding Oaks have thus developed a high sense of community.

Thanks to the association, the neighborhood maintains active social calendar. Winding Oaks residents mostly socialize at gatherings hosted at the community pool’s area nestled amid more than 4 acres of private nature park and pathways.

Typical get-together occasions include monthly luncheons for the neighborhood’s ladies’ and men’s groups. Community belonging is also promoted through neighborhood outings, such as group visits to nearby points of interest like the Mote Marine.

In addition, membership access is open at the nearby Bay Isles Beach Club on Gulf of Mexico Drive. Besides its private beach, the club’s amenities include pavilions, grills, restrooms, private showers, lockers and beach volleyball. It also accepts member reservations for special events.