Lakeside community with small town Old Florida charm
Windermere was once a vacation destination for affluent retirees, drawn to the community’s elegant homes along the Butler Chain of Lakes and its small-town Old Florida charm. In the past 10 years, not much has changed except the addition of younger families making Windermere their full-time home. “Our schools are A-rated, and the community has a lot of family-friendly events, which I think is a big draw,” says Toni Marie Cafferty, a real estate advisor with Compass Florida who sells throughout Central Florida. Today, Windermere is home to about 3,000 people who enjoy its beauty, privacy and proximity to bustling Orlando, about 20 miles away.
Windermere was once a vacation spot for retirees, drawn to its homes on the Butler Chain of Lakes.
Windermere has evolved, with younger families making it their full-time home.
Windermere, home to 3,000 residents, offers beauty, privacy, and proximity to Orlando.
Family-friendly events attract many families to make Windermere their home.
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Elegant homes along the Butler Chain of Lakes
Windermere is made up of multiple neighborhoods, many of which are gated. The standout is Isleworth, a small, luxury community hemmed in by lakes Bessie, Louise and Butler. Sprawling multi-million dollar Mediterranean and French Provincial-style estates sit on landscaped lots, with backyard pools and lake views. Isleworth is the neighborhood where many of the town’s famous residents have lived over the years, including Tiger Woods and Shaquille O’Neal. Other popular neighborhoods include Reserve at Lake Butler Sound and Keene’s Point. Both communities offer large New Traditional and Mediterranean-style homes typically ranging from $1 million to $3 million and sitting on manicured lawns. Townhouses and condos are also available, clustered mostly on the west side of town, offering amenities like lake views, pools and playgrounds.
Million-dollar Mediterranean estates are found in Isleworth, a gated community in Windermere.
This new traditional-stye home in Windermere features an extravagant pool.
This Mediterranean-style mansion sits on a beautifully manicured lawn in Windermere.
Windermere features many gated communities, with Isleworth being the standout.
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Children attend highly rated Orange County Public Schools
Orange County Public Schools serves the area and rates an A-minus on Niche. Windermere Preparatory School is one of the standout private schools in the community. The A-plus rated school serves prekindergarten through 12th grade and was dubbed the best private school in the Orlando area by Niche.
Windermere Prepratory School is a standout private school in the community.
Windermere is served by Orange County Public Schools, which received an A- rating from Niche.
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Fishing and boating in lakes, golf and pickleball at the country clubs
Residents enjoy easy lake access, where boating and fishing are the most popular activities. Country club memberships are not included with neighborhood HOAs, so many residents join Isleworth Golf & Country Club or The Golden Bear Club at Keene’s Point for golfing, tennis, pickleball and swimming. The town also has more than 10 parks, including Central Park which has a large playground for older kids and a smaller one for toddlers, and Lake Bessie Lakefront Park which offers a scenic biking and walking trail. Residents also use their neighborhood streets to get exercise. “You always see people out riding their bikes and walking their dogs,” Cafferty says.
Windermere residents enjoy easy lake access, with boating and fishing as popular activities.
A Windermere resident enjoys daily fishing with direct lake access.
The Golden Bear Club at Keene's Point offers a premier golf course in Windermere.
Windermere Country Club residents enjoy golfing at the prestigious Golden Bear Club.
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Shops and restaurants along Main Street; Restaurant Row in Dr. Phillips is nearby
Residents walk along Main Street to visit locally owned shops and restaurants. The weekly Windermere Farmers Market takes place at Town Square Park. The Grove shopping center is just outside of town and has a Publix, LA Fitness and more local restaurants. Windermere is also close to Restaurant Row in Dr. Phillips, a stretch along Sand Lake Road filled with a mix of high-end and casual restaurants, big box stores and a range of services.
Windermere is close to two large hospitals, the Orlando Health Orlando Regional Medical Center near Route 429, and Orlando Health Dr. Phillips Hospital near Interstate 4.
Windermere residents stroll along Main Street to visit local shops and restaurants.
The weekly Windermere Farmers Market is held at Town Square Park.
Windermere residents stay active at LA Fitness, just minutes away in The Grove shopping center.
Windermere is close to two large hospitals, including Orlando Health Dr. Phillips Hospital.
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Windermere Wine and Dine and Food Truck Night bring residents together
The Windermere Wine and Dine is one of the most popular events, taking place each February and offering sample dishes and drinks from local restaurants. Food Truck Night is also popular, occurring the fourth Friday of each month between September and May at Town Square Park. Each evening is filled with live music, kid-friendly activities and 15 to 20 food trucks.
A look at Windermere's weather and crime
Windermere’s weather is similar to other parts of Central Florida, with temperatures in the 90s from June to September and the low 70s to the mid-80s the rest of the year. Humidity is often high, and summer brings frequent afternoon thunderstorms. While its location inland can often protect the town from hurricanes, residents pay close attention to storms as they develop, as high winds, tornadoes and flooding can occur. In 2024, the town sustained mild damage from Hurricane Milton.
According to the Windermere Police Department, the town saw 70 arrests in 2023, down from 181 in 2022. There were 223 incident reports in 2023, up from 161 in 2022.
Florida's Turnpike and I-4 travel throughout the state
Florida's Turnpike and Interstate 4 are just outside of town and travel throughout the state. The closest airport is Orlando International Airport, about 15 miles away.
Written By
Sara Huffman
Photography Contributed By
Jeffery Palmer
Video By
Scott Wiggins
Interested in learning more about homes in this area?
Reach out to
Christine Johnson,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Windermere, FL sell after 68 days on the market compared to the national average of 52 days. The median sale price for homes in Windermere, FL over the last 12 months is $675,750, up 2% from the median home sale price over the previous 12 months.
Introducing a rare opportunity to own a truly remarkable lakefront estate in the heart of Windermere's prestigious Lake Burden South community. This 5,102 sq ft modern contemporary masterpiece offers 5 spacious bedrooms, including two luxurious primary suites—one upstairs and one down—plus a dedicated office, versatile flex room, and massive bonus/media room, 5 full bathrooms, 2 half baths, and a
Nestled in the TRUE TOWN of WINDERMERE is this Absolutely stunning, meticulously maintained POOL home with TALL CEILINGS and lots of land surrounding you on both sides! Surrounded by majestic mature oaks on a private .74-acre conservation lot in quiet, highly desirable Windermere Reserve with access to the Butler Chain of Lakes. Enjoy serene views from most rooms in this rarely available
One or more photo(s) has been virtually staged. The Sweetwater floorplan offers expansive living with its thoughtfully designedtwo-story layout. This home features six spacious bedrooms and four and a half bathrooms, perfectly accommodating larger households orguests. With over 4,400 square feet of living space, the Sweetwater includes both a flex room and multiple bonus spaces, offering
Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless
Situated within the prestigious and highly coveted community of Keenes Point in Windermere, this exquisitely home refined luxury living. Featuring six expansive bedrooms and six impeccably designed bathrooms, every detail of this residence has been thoughtfully elevated, blending timeless elegance with contemporary sophistication.At the heart of the home lies a chef-inspired kitchen,
Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! Experience the perfect blend of elegance, comfort, and versatility in this stunning 5-bedroom, 4.5-bathroom home in the prestigious Windermere community. Boasting a fully-equipped mother-in-law or older kid suite above the garage, this separate studio apartment offers privacy, abundant space, and its own entrance—ideal for guests, extended
One or more photo(s) has been virtually staged. Experience luxury Florida living at its finest in this stunning one-story custom home, perfectly situated on nearly an acre in the sought-after Lake Cypress Cove community of Windermere. With approximately 3,000 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom split floor plan offers both privacy and an open, inviting
Beautiful renovated 4-bedroom, 2.5-bathroom home offers the perfect mix of modern comfort and resort-style living in an exclusive golf course community. Inside, you'll find spacious living areas, a cozy gas fireplace, and a thoughtfully designed layout ideal for both everyday living and entertaining. The updated kitchen and bathrooms, along with generously sized bedrooms. Step outside to a
WELCOME HOME TO CASABELLA. A LUXURIOUS WINDERMERE FLORIDA, GATED COMMUNITY, SOLAR HOME.Nestled on CLOSE TO AN ACRE lot, this home features 5BR/6.5Bath’s, and offers a feast for the senses with Spanish style architecture. Enjoy plush landscaping, gorgeous hardwood floors, soaring ceilings, and an expansive living room boasting a full wet bar. Retreat and relax after a hard day’s work at your
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