Live Among the Lake in Windermere. A lifestyle like no other with the famed "Butler Chain of Lakes" right at your fingertips. The Town of Windermere is overflowing with history, charm, and an "old town" sense of family.  11 community parks, community docks, tennis courts, rowing clubs, nature trails, and award-winning restaurants. The annual community runs, a weekly farmer’s market and monthly food truck nights add to this all-encompassing and one-of-a-kind location! Interestingly, only the main roads are paved as the town has resisted paving the side roads. Residents feel that this helps preserve the uninterrupted beauty and charm of the area. Windermere is also home to world-class golf courses played on by a number of famous golfers such as Tiger Woods. When it comes to real estate, Windermere serves a variety of property types from sprawling, multi-million dollar, luxury estates to beach cottages, apartments, and townhomes. Becoming one of the most desirable zip codes in Central Florida, Windermere has been able to keep its exclusivity and charm. When the sky turns dark, put your eyes on the sky, you may just see the fireworks shows from Walt Disney World and Universal Studios! 

Sunset over the lake in Windermere, Forida Statue of horse painted with American flag in Windermere, Florida Lake views in Windermere, Florida Clock tower in Windermere, Florida Park bench on a street in Windermere, Florida

Search Windermere Real Estate Listings

About Windermere, Florida

Windermere, FL is located in Southwest Orange County, approximately 14 miles from downtown Orlando, and 6 miles north of the Walt Disney World Resort. It has a population of approximately 3,500, over a total area of 1.57 square miles.

Known as the “Town of Lakes”, Windermere is surrounded by beautiful sand-bottom lakes, including Lakes Butler, Down, and Bessie. Through a series of canals, these lakes also connect with 6 additional lakes, forming the Butler Chain of Lakes. Windermere was founded in 1887 and is one of the oldest towns in Orange County. It prides itself on many of its historical sites, from its Town Hall (completed in 1924) to Cal Palmer’s office building (completed in 1911), and the Historic 1890 Windermere Schoolhouse, the first school in the area. Many of the town’s streets remain unpaved to continue its commitment to retain the pristine nature of the area.

With its proximity to Orlando and lake access, Windermere’s luxury neighborhoods are home to much of Orlando’s elite. Residents include everything from corporate executives to local entrepreneurs, celebrities, actors, and athletes. Former NBA player Shaquille O’Neal is a noted resident.

Windermere Real Estate

Windermere real estate offers a quaint refuge from the hustle and bustle of Orlando’s theme parks and tourist areas, with a decidedly “old town Florida” feel. With its traffic-relaxed streets, unpaved roads, and white concrete signs, this historic enclave is a highly sought-after community for everyone from families, to retirees, to celebrities. The community is surrounded by a chain of lakes and canals, meaning residents can easily find a home on the waterfront, or one with a lake view. Due to its popularity, Windermere has slowly added upscale subdivisions with luxury properties, including the exclusive Isleworth, Reserve at Lake Butler, and Chaine Du Lac neighborhoods.

Windermere real estate offers the finest in super-luxury properties, with spectacular estate homes in gated communities or lakefront access. Often featuring exquisite Mediterranean architecture, soaring ceilings, 8-10 bedrooms, and lavish features like fountains and indoor pools. Gourmet kitchens offer professional-grade appliances, climate-control wine cellars, and humidors. Properties feature extensive outdoor entertainment areas, beautifully designed pools, and lakeside docks. But Windermere also offers plenty of selection of more modestly-priced homes, from single-family homes in quiet neighborhoods close to shopping and schools to spacious condos and townhomes in complexes with extras like pools, sports courts, and other amenities.

Single-family homes in Windermere often feature 4-5 bedrooms, with large open kitchens and entertainment areas. Premium features like granite countertops, stainless steel appliances, and walk-in closets are common. Most properties offer lanais for the ultimate in indoor/outdoor relaxation, as well as beautiful outdoor terraces, pools, or lushly landscaped yards.

Find The Home Of Your Dreams

View The Latest Florida Real Estate Listings

Start Searching

Windermere Attractions

Windermere, FL is the perfect location for those who want upscale living, with a small-town feel, within driving distance of all the urban amenities one could need. Nestled in the heart of the Butler Chain of Lakes, it is a relaxed, picturesque area, with great outdoor amenities and even more in neighboring communities.

Charming downtown Windermere consists of three blocks of commercial space, with small local shops, boutiques, cafes, and restaurants. Favorite local spots include the Dixie Cream Cafe, Allen’s Creamery and Coffee House, Rokka Market, and Paloma Coffee Co. The Windermere Farmer’s Market is hosted along Main Street every Friday and attracts vendors and visitors from all around the area.

Major shopping centers, including grocery stores and big-box retailers, are mostly located minutes outside of the Windermere area. The Grove, only a mile east along Windermere-Conroy Road, is an upscale outdoor shopping plaza with groceries, banks, restaurants, and other essentials.

The main attraction for Windermere residents is the beautiful sand-bottom lakes surrounding the area. The Butler Chain of Lakes is one of the few clean chains of lakes remaining in Central Florida and is a haven for fishing, boating, wakeboarding, and waterskiing. The lakes also house an array of wild species, including pelicans, turtles, hawks, and crocs/gators. Lake cruises are another popular activity for residents and visitors alike.

Windermere features a large number of community parks, featuring lush green spaces, playgrounds, sports courts, and walking paths. Some also feature lake access, fishing piers, and wetlands areas. The nearby Tibet Butler Nature Preserve is a 483-acre refuge, featuring trails and boardwalks accessing unblemished wetlands, pine forest, swamp, and lakeshore lined with cypress trees.

There are many fantastic golf courses within minutes of the Windermere area. The Isleworth Golf & Country Club is a prestigious club and community located on the shores of Lake Louise. The Golden Bear Club features a Jack Nicklaus-designed course and luxury clubhouse.

With such close proximity to Orlando, Windemere residents can enjoy endless shopping, dining, recreational, and entertainment possibilities. For a taste of the area’s arts and culture, be sure to catch performances by the renowned Orlando Philarmonic or Orlando Ballet. Disney and Universal Studios theme parks, Sea World, and other attractions offer a vast amount of entertainment for the entire family.

Walt Disney World Resort is only a 15-minute drive away and is so close that Windemere residents can watch the Magic Kingdom’s nightly fireworks display from the comfort of their own yards.


What is Windermere known for?

Situated between a series of gorgeous lakes, Windermere is known for its natural beauty and historic charm. This Central Florida city has plenty of waterfront properties, as well as easy access to nature trails and lakefront parks. In addition, there are several world-class golf courses nearby, making this a prime golfing destination.

How far is Windermere from Orlando?

Windermere is just 15 miles west of Orlando. Takes about 25 minutes to drive from Windermere to Orlando along the FL-408 E depending on traffic. 

Is Windermere a good place to live?

Windermere is an upscale community that feels very safe, well-maintained and peaceful. With easy access to lakes and trails, it’s easy  to live an active lifestyle in Windermere. There is a wide array of amenities within the community including restaurants, shops and cafes, and Orlando is just a short drive away.

Does Windermere get hurricanes?

Due to its inland location, Windermere is at very low risk of hurricanes. However, during the rainy season between June and November the city can experience heavy rains and strong winds.

Is Windermere a good place to invest in real estate?

Real estate in Windermere is highly sought after thanks to the city’s ideal location amid the Butler chain of lakes and close to Orlando. You’ll find many lakefront homes for sale, as well as single-family homes on quiet residential streets. Real estate can be a good investment here, as you can find stunning homes for less than you would pay for the same square footage in Orlando.

Windermere Real Estate Stats

Average Price $1.5M
Lowest Price $305K
Highest Price $22M
Total Listings 905
Avg. Days On Market 176
Avg. Price/SQFT $362

Property Types (active listings)

Kari Fleck, Owner & Broker

From Atlantic Coast To Gulf Coast - The Real Estate Expertise You Deserve

Get in touch
florida beach, wooden stairs

Start searching for your dream home now.

When it comes to convenience, our site is unparalleled. Whether you're in the comfort of your home, or on the go.
Our site works flawlessly on multiple devices so you can find the information you need.

Start Search