Located right by Horizon West, Winter Garden, and Doctor Phillips, Windermere is in the perfect spot for those looking to live near everything. This area is a little smaller than the rest, but it’s known for its luxury waterfront homes right off of Lake Butler. This lake is a popular spot in Windermere for boating, fishing, and more for residents, with the Butler Chain of lakes considered one of Florida’s most sought after areas offering waterfront homes. Other than this, there are multiple cafes and coffee shops along Main Street nestled right between Lake Butler and Lake Down, with some parks throughout.

If you or your family are looking for a luxury home on the water, or just a nice area to be right in the middle of everything, then Windermere is the place for you! Click to read more about Windermere real estate.

Historic police station in Windermere, Florida and welcome sign

Windermere, FL Real Estate Statistics

Average Price $2M
Lowest Price $318K
Highest Price $22M
Total Listings 303
Avg. Days On Market 92
Avg. Price/SQFT $418

Property Types (active listings)

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Discover More About Windermere, FL

Situated between Lake Butler and Lake Down is the small, charming town of Windermere, Florida. This community is only a little about 1.5 square miles in size, but its peaceful atmosphere, great location, and gorgeous properties attract many homebuyers. As of 2021, Windermere, Florida has a population of just over 3,000.

Directly south of Windermere is the beautiful community of Isleworth. The census-designated place of Lake Butler (of which Isleworth is part of) completely surrounds the town of Windermere on all sides. Further south, you’ll find Bay Hill and Doctor Phillips, which are considered to be Orlando suburbs.

Explore Windermere Real Estate

Because of Windermere’s quaint size, real estate is rather exclusive—and the waterfront homes in particular are extremely sought-after! The market in Windermere consists entirely of gorgeous single-family homes—perfect for those who long for an Orlando lakefront escape.

While the price point for homes in Windermere tends to lean heavily into the luxury category, you can find older homes in the area for more affordable price points. Typically bungalows, these properties have a construction date anywhere from the 50s to the 80s, which could be the ideal choice for someone who isn’t always keen on the ultra-modern look of contemporary homes. 

However, despite being older properties, Windermere homeowners tend to carry out extensive interior renovations. Generally, real estate in this area is very modern from the inside, with luxurious upgrades and open floor plans. You will rarely find homes for sale in Windermere that need a lot of TLC. Instead, custom builds and unparalleled luxury are standard. There are also a select number of historic properties in this town, some over one hundred years old, and they too have been expertly maintained. 

Windermere’s excellent location on several lakes means that there is ample opportunity to own a waterfront property. These lakefront estates aren’t constrained to one particular architectural style; you’ll find typical suburban designs, traditional styles, and even Mediterranean-inspired homes. Large lot sizes, incredible interior features, and private water access are all typical attributes of the luxury waterfront homes for sale in Windermere


Windermere Highlights & Amenities

Incorporated in 1925, Windermere has a lot to offer its residents and visitors.

Most of the town is residential, but Windermere’s historic downtown area is within walking distance from almost anywhere—thanks to its size! Centered on Main Street, the town has preserved the cobblestone roads and the historic look and feel. With small local shops and restaurants, this area is incredibly charming and beautiful to stroll around—with tall trees providing a lush canopy over the street.

The Windermere Town Square, also located on Main Street, is a point of interest as well. Here you’ll find a park, the Windermere Town Hall building, the Cal Palmer Memorial Building and 9/11 Memorial, and the Windermere Branch Library. There are many events that are held throughout the year in Town Square Park, including the Windermere Farmers Market, movie nights, resident 10k runs, and holiday activities. 

A few blocks over is Central Park, another large space close to the center of town. Great for kids, a lot of this green space is made up of playgrounds and green grass to run around in. As an alternative, The Pines at Windermere is found in the north end of the town. This park offers a baseball, volleyball, and soccer field, event rooms, and more, but is available by reservation only.

A number of other parks are located around Windermere. Palmer Park is found near the waterfront, whilst Park Among The Lakes (a private access area) is where you’ll find the town’s tennis courts. There is also a boat launch at Fernwood Park, where you could sail to Bird Island or just take a trip out on Lake Butler. 

Get To Know Windermere, FL

Windermere, FL FAQs

Is Isleworth considered part of Windermere?

Isleworth is not officially part of Windermere, although this has been a point of contention for many years. Butler Bay, however, was annexed in 2007.

How big is Windermere, FL?

The town of Windermere is a relatively small community at only about 2.7 square miles in size, with a population of just over 3,000. But Windermere does extend to the areas surrounding the lakes.

Do celebrities live in Windermere?

Windermere has been a popular destination (owning and renting) for numerous high-profile celebrities.

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