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Winding Oaks

Winding Oaks 

Aspiring buyers of Longboat Key residences for sale will find the townhomes of Winding Oaks a delightful consideration. This neighborhood is tucked in one of the coziest locations within Bay Isles, a master-planned gated development of 16 residential communities. All share a sprawling prime site with the scenic Harbourside section of the posh Longboat Key Club.  

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

Major Neighborhood Updates

Prospective buyers of Winding Oaks residences for sale will likewise be delighted to note the recent upgrades worth nearly $3 million that have been undertaken in this community. 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 townhome residence.

Single-family Home Feel

Available homes in this neighborhood, however, come few and far between on the market, as it consists of just 56 maintenance-included townhomes. Designed Nantucket-style, these residences are in either two- or three-bedroom configurations within floor plans ranging from over 2,000 to almost 2,700 square feet. Their price points typically start from the high $500s and top at around the $900s.

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

Delightful Leisure Opportunities

Residents enjoy membership access to 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.

A hands-on homeowners association and board of directors manage Winding Oaks. Pet-friendly, this community further provides delightful living through regular social activities, such as book and card clubs, parties, and various committee opportunities.

Work With The Judy Kepecz-Hays Team

Dive into luxury with the Kepecz-Hays Team, renowned realtors for Florida's Central West Coast, emphasizing Longboat Key, Lido Key, and Sarasota. With an impressive $2.4 billion in career sales, our team combines an expansive international network with expert marketing strategies. For buyers, we offer a select range of premier properties and private viewings. Experience the best of Sarasota County — its pristine beaches, arts, paddle sports, and shopping. From insightful neighborhood guides to tips for seamless buying and selling, we're your key to Florida's elite real estate. Choose Kepecz-Hays Team for unparalleled excellence.