Before I scare you with the fact that Windermere is the suburb with one of the highest median home prices in Central Florida, let me mention that Windermere makes up a large land area. Certain sections of Windermere have price tags closer to the 300s, but can be tricky to find. Townhomes can still be found under $250,000, and single-family homes for under $300,000. Windermere has been the “it” neighborhood for decades. With a higher budget comes beautiful homes, unbeatable location, and lots of lakes. Exploring Windermere feels like a treat — you can easily imagine living in a beautiful house in a beautiful neighborhood here. It’s also located right behind the Magic Kingdom. But we’ll get to that in just a minute.

History & Location

Windermere is located directly north of Disney, in a pocket of natural beauty called the Windermere Chain of Lakes. Downtown Windermere feels historic and upscale. You’re invited into the downtown with brick-paved roads, large oak trees, roundabouts, and mature landscaping. Downtown Windermere is the smallest downtown of all Orlando suburbs. The area only features 4 or 5 shops and can be quickly walked through within 15 minutes or so. This area is more for passing through, although it makes a beautiful drive. There are two coffee shops, a spa, a café, and a few other professional stores.

I’ve noticed over the years that homes closer to Downtown Windermere are older and have larger lots. The further out from downtown you drive, the newer the home and the newer the subdivisions. This is definitely not a con, as homes in both areas can sell in the multi-millions.

Windermere Map and relative distance to theme parks


The most exclusive neighborhood in Windermere is Islesworth. Homes in this neighborhood have sold for up to $23 million (homes complete with an underground 40-car garage), but the vast majority are in the 1-6 million dollar range. This ultra-private gated community is perfect for those that value privacy. Interestingly, the land Islesworth sits on was purchased by Arnold Palmer in the 1980s, where he constructed an award-winning golf course. The golf course is widely regarded as the most difficult in the state of Florida. The land was later sold to Tavistock Group (also the creators of the award-winning city of Lake Nona) who developed the land into what Islesworth is today.

One of the absolutely most amazing parts of Windermere is its proximity to the Magic Kingdom. It’s so close that cast member parking is right off Reams Road. As you drive down Reams, you can see the inner workings of Disney. Spot the Disney University building, cast member parking, and even views of the top of the castle.

Disclaimer: Even though this area is within walking distance to Disney property, the commute time from the Reams Rd area to Magic Kingdom parking is still about 15 minutes for non-Disney cast members. This section of Windermere is also one of the most affordable too! In this area, you can buy a single-family home under or around $300,000. Not bad when you have nightly fireworks show included!

Depending on the neighborhood, townhomes and some single-family homes start right under $300,000 to over $1 million in this part of Windermere. Neighborhoods like Carrington and Mabel Ridge are the most affordable subdivision off Reams Rd. Other nearby neighborhoods with larger homes can easily stretch to over a million, like The Enclave.

Why Live Here?

Firstly, for the address. The Windermere name is widely known as one of the most prestigious neighborhoods in Orlando. The second reason is the proximity to parks. From Windermere, you’re a 15- to 20-minute drive to Disney, many routes accessible by back roads!

Homes for Sale in Windermere

If you have questions about moving to Central Florida and would like to speak with a real estate professional, please contact us. You can also review the listings below and contact us regarding a property you’re interested in.

CLICK HERE to search homes for sale in Windermere, FL

Pete Werner

I'm an Orlando local and owner of The DIS (wdwinfo.com), DVCfan.com, DCLfan.com, and host of the DIS Unplugged podcast.

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