Windermere is an affluent and exclusive community within Orange County and close to Orlando.

Welcome to Windermere


A charming residential neighborhood full of wholesome family fun.

Windermere is an affluent and exclusive community within Orange County and close to Orlando. Their town motto is “Among the Lakes” because it is on an isthmus stretched across the Butler Chain of Lakes. The neighborhood is made up of large homes. Bordering Disney World to the North, the theme park’s nightly fireworks show is visible from several points. 

What to Love

  • Convenient access to the Butler Chain of Lakes
  • Dog-friendly. Pets are welcome at various venues.
  • Seasonal attractions and opportunities to get a taste of fresh, local produce.

Local Lifestyle

Windermere loves their pets. All four-legged furry residents are celebrated and catered to at the PetFest. Attendees enjoy listening to live music, watching the police K-9 demonstrations, and entering their pets in fun contests to win trophies. There are dedicated play zones and activities for both the pups and the kids. 
Town Square Park is the heart of town and where many Windermere’s weekly, monthly, and yearly events take place. The Farmer’s Market occurs every Friday. A cornucopia of fresh produce and artisanal wares is a feast for the eyes or stomach, whether you’re shopping or just browsing. Pets are allowed if they wear a leash and behave well. On the fourth Friday of every month, the popular Food Truck Night rolls into town. Crowds gather to sample the many cuisines. 

Dining, Entertainment & Shopping

Locals adore the quirky atmosphere at Yellow Dog Eats, a dog-friendly joint serving inventive, flavorful barbecue along with tasty vegetarian and vegan options. You can indulge in a Southern-style brunch and hot coffee or chilled mimosa out on the patio at Dixie Cream Cafe, located on Main Street. Feather & Quill is the spot for scrumptious New American fare and signature craft cocktails. Try their Duck & Tuck pizza with house-cured duck prosciutto, almond pesto, and Manchego, and pair it with their Call the Sitter cocktail made with Butterfly Pea Flower infused gin, elderflower liqueur, lemon tonic, and mint. Connected to the restaurant is Propag8, their password-protected speakeasy tailored to cocktail and plant fanatics. 
As a creative outlet, The Art Room teaches a range of classes, from painting to sculpting. The art studio also hosts all-day workshops featuring renowned visiting artists who share their expertise. The knowledgeable staff of Tim’s Wine Market pair customers with the perfect wine. Go for a tasting, and leave with a full bottle, or two. 

Things to Do

Thirteen lakes with excellent water quality link the Butler Chain of Lakes. It is ideal for fishing, boating, and water sports. Boaters are able to access the Butler Chain via the boat launch ramp at R.D. Keene Park. For one-on-one instruction for catching waves, look no further than the Florida Ski School. Hourly boat and equipment rental packages are available to accommodate larger groups. Other R.D. Keene Park amenities available for public use include the soccer fields, picnic areas, and a playground.
Beck Brothers Blueberries (say that three times fast!) is a family-owned ‘U-Pick’ where people can fill up a bucket with farm-fresh blueberries. When it is in season, Beck Brothers sell local orange blossom honey. It makes a sweet holiday gift. 
The annual Run Among the Lakes takes walkers and runners on 5K or 10K scenic routes through town. The marathon benefits Windermere Parks and Recreation services. On the outskirts of Disney World is the naturally beautiful Tibet-Butler Nature Preserve. Patrons are encouraged to check out the nature center exhibits and butterfly garden before embarking on a trail hike.


The community is part of the Orange County Public School district.

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