Featured listings




Some may think of Windermere as a touristy area, but it’s a very nice community in Florida to settle down and raise your family. It’s a growing town, for sure, but it has managed to retain that small-town feel that locals, and even visitors, find so charming. 


Its proximity to Orlando is also what makes the community attractive. You have your own refuge from the chaos and congestion of living downtown, but are close enough that you can go there anytime you want. A lot of white-collar employees and executives are currently living in Windermere.


In the early 1970s, an influx of Disney executives from California moved to Windermere.


Many celebrities and famous personalities have called Windermere their home. For example, Shaquille O’Neal and Tiger Woods have houses here. There’s also Ken Griffey Jr., American golfer Mark O’Meara, Wesley Snipes, and Robert Earl, the CEO of Planet Hollywood. You may also bump into other rich and the famous people whose properties dot the Butler Chain of Lakes.  


Speaking of the Butler Chain of Lakes, it’s one of the most sought-after lakefront areas, not just in Windermere, but the whole of Florida. There are 11 lakes in all that are teeming with wildlife and rich foliage so it feels like you have nature’s playground all to yourself when you buy a property here. The lakes also offer plenty of opportunities for water activities to enjoy.


The 13 lakes are Lake Tibet, Lake Butler, Lake Louise, Lake Blanche, Lake Down, Pocket Lake, Little Fish Lake, Lake Bessie, Lake Louise Lake Isleworth, Lake Chase, Lake Sheen, and Wauseon Bay.


Windermere is an isthmus between great lakes. From here, Lake Down, Lake Butler, Lake Bessie, and Wauseon Bay are very accessible.  They are not to be confused with Lakes of Windermere, which is an exclusive subdivision that offers first-class amenities and higher real estate prices. 


The town hits that sweet spot where it’s not too big to be truly crowded and not too small to be boring. 


Another reason why people find the town so charming is its historical roots. Although Windermere was established as a residential area in 1889, a Post Office opened here a year earlier and Windermere was later chartered in 1925.


For history buffs, they will find some hidden gems here that speak about Windermere’s history. Some buildings are listed in the US national historic registry and those are quite obvious due to the landmarks. But walking around, you will find unmarked sites that date back to the founding of the town. 

In 1950 Windermere’s population was 317 people. In 1980 it was 1,202 and in 2017 the population was 3,302.

Windermere Real Estate

Windermere properties are in high demand. The median value of homes in Windermere is around $445,000 or $177 to $200 per square foot. Renting a house here is also a bit more than other towns in Florida. Rental prices generally start around $2,200 a month.


The property values here are significantly higher compared to the Orlando-Kissimmee-Sanford Metro where the median price of homes is $240,000. The average rent for homes in the metro is $1,645.


But if you are looking at Windermere as your future home, it’s best to buy sooner rather than later. Housing prices here continue to go up as more and more people are falling in love with Windermere’s charm. You can see communities sprouting up and apartments being built left and right here, which tells you that property developers are noticing the rising demand from prospective homeowners. 


From 2017 to 2018, housing prices rose about four percent and they are projected to increase two percent more by the end of 2019. 


However, residents here generally have a higher median income compared to most neighborhoods in the state. There are lots of good reasons for the high property value in here. Try visiting Windermere and you will find why this community is a popular destination for people who are looking for a place to settle down for good.

Living in Windermere


As far as the school system, Windermere is being served by the Orange County Public School District, which also serves Dr. Phillips and Winter Garden. All the schools here are highly rated by the Florida Department of Education.


There are plenty of shopping establishments, entertainment venues, restaurants, and pop-and-mom stores here in Windermere. Of course, downtown Orlando is just a few minutes away if you want a change of pace. If you are a business person who is always out on a business trip, or a frequent traveler, the Orlando International Airport is just a 20-minute drive from Windermere.


Windermere also has plenty of access to healthcare. Windermere is close to Orlando Regional Medical Center, Arnold Palmer Hospital for Children, Winnie Palmer Hospital for Women and Babies, Florida Hospital Orlando, Florida Hospital Cancer Institute, and Florida Hospital for Children, among others.

The distance between Windermere and the Magic Kingdom (Disney World) is 6 miles. The road distance is 8.8 miles.

If you love the beach, St. Pete Beach, Cocoa Beach, Clearwater Beach, Daytona Beach, and New Smyrna Beach are just an hour or two away. It’s a good opportunity for a road trip and it’s also a good escape or change of pace.


Have More Questions About Windermere, FL?

Scroll Up