When thinking about moving to the Orlando area, two names often come up: Celebration and Windermere. While both are close to Disney, they offer very different vibes. This post takes you on a tour of Windermere, Florida, exploring its downtown, various neighborhoods, and a recent listing.
Key Takeaways
- Windermere offers a wide range of homes, from luxury estates to more affordable options.
- Its location provides convenient access to Disney, Restaurant Row, and other Orlando amenities.
- The area features beautiful lakes and established neighborhoods with many updated homes.
- Despite its reputation for luxury, there are many homes available under a million dollars.
Exploring Downtown Windermere
Downtown Windermere itself is quite compact, covering just 2.69 square miles. Unlike some larger nearby towns, it doesn’t have a vast commercial area. However, it’s a growing hub with places like Windermere Brewing and other shops. They also host events like Food Truck Friday on the last Friday of each month, making it a lively spot for residents.
It’s interesting to note that many homes with a Windermere mailing address are actually in unincorporated Orange County areas, which can affect things like school districts and taxes. So, it’s always good to check the specifics when looking at properties.
Why Windermere is a Great Location
One of the biggest draws of Windermere is its location. It’s about a 25 to 35-minute drive to Disney World, offering easy access to the magic without living right in the middle of the tourist hustle. Plus, it’s only about 15 minutes from Restaurant Row, where you can find some of Orlando’s best dining spots. This makes Windermere a convenient base for enjoying all that Central Florida has to offer.
Neighborhoods and Home Styles
As you drive around Windermere, you’ll notice beautiful lakes everywhere. The first major neighborhood you’ll likely see is Isleworth. Made famous years ago by golfers like Tiger Woods and Shaquille O’Neal, Isleworth is known for its luxury homes, many built in the late 90s and early 2000s. Many of these older homes have been significantly remodeled, with some stunning estates on Lake Butler boasting over 11,000 square feet.
Beyond Isleworth is Keene’s Pointe, a larger community with about 1,000 homes. Here, you’ll find a wide variety of properties, ranging from around $950,000 up to $6 million. Keene’s Pointe has many smaller, distinct neighborhoods within it, offering different views like golf course frontage, waterfront lots, or backing up to other homes. It’s a community with a lot of diversity in its real estate.
Even though Windermere is known for its high-end properties, there are plenty of options under a million dollars. You’ll find smaller gated communities, often with 200 to 500 homes built in the early 2000s, especially around the Windermere and Vineland Road area. These homes often feature larger lots, pools, and have seen many updates over the years, offering good value.
For those looking for something more affordable with a Windermere address, Lakeside at Windermere is an option. Located right off 535, this community offers condos and townhouses typically in the $300,000 range, which is quite attractive given the desirable Windermere schools and location.
A Look at a Recent Listing
We recently had a listing in Windermere that really shows what’s available. Built in 2002, this 2,500-square-foot home is all on one level and features four bedrooms plus an office. Since it was built, it has undergone significant upgrades, including new doors, windows, light fixtures, and flooring, bringing it from its original 2002 style to a more modern look.
The heart of the home is the updated kitchen with quartz countertops, which opens up nicely to the rest of the living space. The layout is a popular split floor plan. There are two bedrooms sharing a bathroom, an en-suite bedroom with pool access, and a primary suite that has also been updated.
The outdoor space is a major highlight, with a covered lanai, a heated pool, and plenty of privacy thanks to how the homes are situated and a vinyl fence. The established trees and mature landscaping give it that classic Windermere feel. This home was listed just under $800,000, which is a great price when you consider the cost of building something similar today.
Something for Everyone
From multi-million dollar estates to condos under $300,000, the range of homes for sale in Windermere today is quite broad, from $345,000 up to $16 million. It really does seem like there’s something for almost everyone looking to move to this popular Central Florida area.



