Community Spotlight: Windermere

By Yasmene Warren

Windermere is regarded as being one of the best places to live in Florida, according to Niche. It’s relatively small, but it has a lot to offer including quality schools, luxury homes, and proximity to theme parks and downtown. Let’s check out what it’s got going on!

About Windermere

Windermere is a lively town in Orange County and is one of the best suburbs near Orlando to live in, especially for those on the wealthier side.

According to the 2020 census, approximately 3,030 people live in the town of Windermere. The town is nestled right between Lake Butler and Lake Down, and the total area is made up of 2.69 square miles, 72% of which is water.

Windermere is in close proximity to the city of Winter Garden and is roughly 20 minutes away from attractions like Walt Disney World and is about 12 miles from Downtown Orlando. Some of its public schools include Windermere Elementary School, Gotha Middle School, Windermere High School and Olympia High School, and there is also a private, coeducational PK-12 college preparatory school called Windermere Preparatory School.

Neighborhoods and Home Buying

There are over 40 communities and neighborhoods in Windermere that offer homes, ranging from as low as the mid $300’s and all the way up to $10+ Million.

The average price for a home sold, over the past few months, in Windermere was $1.2 Million for a 4 bedroom home with 4 bathrooms, at 3,000+ square feet.

Let’s dive into what separates these neighborhoods from one another!

Lakes of Windermere

Lakes of Windermere is a quiet community that sits on the south end of Lake Sawyer in Windermere. This neighborhood comes complete with amenities like a community swimming pool, a pier, a sports complex, a gazebo at Pine Loop Park, and three playgrounds.

This oak tree-lined community offers a variety of single-family homes in Victorian, Craftsman and Classic styles with porches and rear entry or front garages. Homes here can range from $500K to $700K.

Reserve at Lake Butler Sound

Reserve at Lake Butler sound is a guard-gated luxury waterfront community in Windermere that sits on the south end of Lake Butler. Its amenities include the sanctuary, which is home to a variety of exotic wildlife, the sculptured Cartmel Gardens and the casual Keswick Garden.

This community’s abundant access to nature makes for the perfect place to hold social gatherings, go on long, scenic walks, and just kick back and relax in peace and privacy. Homes here start at $750K and can go up into the multi-millions.

Windermere Club

Windermere Club is an upscale community that lies home to the Windermere Country Club and Golf Course. It is a private community with about 148 homes, some of which have lovely waterfront views of the Butler Chain of Lakes. Most homes in this neighborhood are listed in the low millions, but some start at $750K.

Keene's Pointe

Keene's Pointe is a country club community right off of the Lake Butler Chain in Windermere. It offers beautiful conservation areas, playgrounds, and the Golden Bear Club that features a Jack Nicklaus designed golf course. Prices for a home in this community can range from the mid $700's to $5+ Million for a 3 to 6 bedroom property.


Windermere Homes sold by The Pozek Group in Keene's Pointe

Closed on 9/26/22 for $915,000

Closed on 1/7/23 for $919,000

*Isleworth is also a community within the vicinity of Windermere, but was never officially incorporated into the city after a proposal with the county in late 2007.

Things to Do in Windermere

Windermere is more than just a ritzy town with big houses that offer lakeside views. This tight-knit community has quite a few things to keep its residents occupied.

Drinks and Dining

You can pick your own blueberries at Beck Brothers Blueberries U-Pick, sip on a beer and enjoy the lake views at Windermere Brewing Company, or craft your inner artist at The Art Room.

For fine dining, you can channel your inner Italian at Bella Tuscany, order from Hawkers Asian Street Fare, grab brunch at Dixie Cream Cafe and much more.


Windermere is relatively small, but luckily, its central location keeps you in close proximity to all the major shopping centers!

You can go to the outdoor mall in Winter Garden called Winter Garden Village, drive east on Conroy-Windermere Road toward the Mall at Millenia, or shop at the West Oaks Mall in Ocoee.

Windermere Farmer's Market

If you’re looking to shop local, there are also specialty shops like Windermere Art & Framing, Five Star Florida Finds, Tim’s Wine Market, Pistil Home & Garden and Elysium Interiors. Every Friday you can also catch the Windermere Farmer's Market for local produce, homemade goods, and more with varying local businesses every week!

Parks and Recreation

One of Windermere’s greatest aspects is being able to become one with nature. There are an abundance of parks around the town for people of all ages to enjoy.

At the Windermere Recreation Center, you’ll find a kayak launch, a dock and boardwalk, a sand volleyball court, a walking path, a doggie waste station, barbecue grills, a bridge to a small island on Lake Crescent, a tennis court, grassy areas and rentable open-air pavilions.

Image by Town of Windermere - Windermere Recreation Center Tennis Courts

There’s also Lake Bessie Lakefront Park, which offers a boat ramp and a walking/biking trail.

Town Square Park is home to the town hall, the Franklin W. Chase Memorial Library, basketball courts, and the soon-to-be Windermere Pavilion. This park also poses as an event center and hosts annual events such as Pet Fest, Wine & Dine, Windermere Farmers Market, 5K/10K Run Among the Lakes, Family Food Truck Night, Craft Beer Fest, Light Up Windermere and more!

Image by Town of Windermere - Windermere Town Hall



Windermere is a thriving suburb with a lot to offer despite its smaller size. It’s definitely on the more expensive side, and if that’s your cup of tea, then this may be the perfect place for you. This town’s small size comes with a big community, and it’s not too far from all of what greater Orlando has to offer. If you’ve been convinced, let our team help you find your dream home in Windermere!


The Orlando Real is sponsored by The Pozek Group. If you’re thinking of buying or selling a home in Orlando, reach out and we would love to help!

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