Orlando's Convenient Suburb Is A Glamorous Enclave With Fine Dining And Sparkling Lakes

People visit Orlando for Disney World, Universal Studios, and Islands of Adventure; however, there's so much more to see than just Florida's amusement parks. One such example is a quiet, isolated neighborhood that lies about 30 minutes away from the Orlando International Airport (and 20 minutes from Disney World), surrounded by upscale restaurants and country clubs with glittering lakeside views. Windermere is an enclave that is a part of the Butler Chain of Lakes, extending to 13 lakes in total. Here, the water quality is so clean, it was the first Florida lake chain to receive an Outstanding Florida Waters honor from the Florida Department of Environmental Protection in 1985.

Many people enjoy recreational water sports like fishing, kayaking, and paddleboarding here. You can travel through more than 30 connecting canals, where outdoorsy visitors can bask in the sunset or gawk at the massive mansions with lakefront properties. Many of these prime real estate homes belong to prestigious and red-carpet-worthy owners, so you may also squeeze in some stargazing as well.

Along with an awe-inspiring landscape in an exclusive neighborhood comes an even better culinary scene. You can taste handcrafted cocktails at chic lounges or have your mouth water over impressive dishes, cuisine that draws both locals and travelers alike. The sophisticated gastronomy sets the stage for Windermere's roster of high-profile residents, their celebrity estates tucked away along the shoreline.

Posh, star-studded Los Angeles neighborhoods aren't the only places you'll find your favorite stars. NBA royalty and hospitality extraordinaires have been reported to call Windermere home. From basketball superstars Shaquille O'Neal and Vince Carter to pop sensation Joey Fatone, the neighborhood has boasted, and still does, some of Florida's most recognizable homeowners. "The Queen of Versailles," Jackie Siegel, and her late husband, David Siegel, the founder of Westgate Resorts, began constructing what's been intended to be one of America's largest homes in the enclave, reaching nearly 90,000 square feet. The median house listing price in the area in October 2025 was close to $1 million, so those who live here definitely have to exist within a certain tax bracket.

Celebrities and high-profile clients tend to choose Windermere as a place to set roots because Florida has no state income tax, the neighborhoods are gated, and many local homeowners get to experience life on the lake. In short, they're getting the best of all worlds in Florida: sunny skies and palm trees as well as peaceful, waterfront privacy that feels a world away from the downtown hustle.

Windermere is also a great place to meet like-minded people in a community environment by becoming a member of exclusive golf & country clubs, like Isleworth. As per Listed Luxury, a membership at Isleworth has an initiation fee of $100,000 and up.

Windermere, Florida, provides more than just a feast for your eyes, with the various restaurants in town ensuring a feast for your stomach, too. You can get a mix of casual chains, like Hawkers Asian Street Food, or try a fine dining gem, like Bella Tuscany. At a Hawkers, your taste buds will be transported around the globe to Asia as you feast on bao buns, spring rolls, and teriyaki udon noodles. Locals and visitors alike are fans of this eatery, as evidenced by the near-5-star rating on Google after more than 4,300 reviews. If you're looking for Italian fare, Bella Tuscany offers classics including chicken parmigiana, spaghetti and meatballs (their best seller), and more. A well-regarded spot, it's on TripAdvisor's top 10 best restaurants around Windermere.

Another delicious dining option is Manzzo Cuisine. An upscale establishment that serves classic Italian dishes, it's similar to Bella Tuscany but with a "create your own pizza" option. Manzzo isn't just the swanky type of restaurant Windermere visitors are looking for; it's also relatively new, having celebrated its one-year anniversary in October 2025. For those wrapping up a day on the lake or getting in that last swing at Isleworth, Windermere's restaurants surely won't disappoint.

Want to spend the holidays in nearby Orlando? See our feature on why it was named America's "Happiest Holiday Destination."