$1,245,218Average Value$297Average Price per Sq Ft43Homes For Sale
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
Tyler Belile
Interested in learning more about homes in this area?
Reach out to
Gwendolen Flynn,
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.
View GreatSchools Rating Methodology
On average, homes in Windermere, FL sell after 62 days on the market compared to the national average of 70 days. The median sale price for homes in Windermere, FL over the last 12 months is $530,000, down 15% from the median home sale price over the previous 12 months.
Welcome to Refined Living in Tuscany RidgeStep into luxury with this fully renovated, move-in-ready home, perfectly situated in the exclusive, gated community of Tuscany Ridge. Every detail of this exquisite residence has been thoughtfully updated to offer modern elegance, comfort, and timeless sophistication.The main level features a spacious primary suite designed to evoke a
Welcome to a home that isn’t just designed—it’s curated.Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the second floor. Every detail intentional. Every space
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 quartz countertops, cherry cabinets, and stainless
Welcome to Refined Living in Tuscany RidgeStep into luxury with this fully renovated, move-in-ready home, perfectly situated in the exclusive, gated community of Tuscany Ridge. Every detail of this exquisite residence has been thoughtfully updated to offer modern elegance, comfort, and timeless sophistication.The main level features a spacious primary suite designed to evoke a
Welcome to a home that isn’t just designed—it’s curated.Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause. Nearly 7,000 square feet of single-level, custom-crafted living plus more than 800 square feet private media room on the second floor. Every detail intentional. Every space
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 quartz countertops, cherry cabinets, and stainless
Coming soon. August 1st ready. Beautiful and elegant single-family mediterranean home with 4 bedrooms and 2 bathrooms, and a 2 car garage in the desirable community of Enclave in Windermere. This home starts with a great curb appeal - meticulously landscaped front, paver driveway, and elegant tiled roof. The community is located within minutes of restaurants, shopping and entertainment. Tiled
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
Situated 13 miles southwest of Orlando and bordered by Lake Tibet, Bay Hill offers residents access to prime Central Florida living. “Bay Hill is a fantastic upscale golf community that is nestled right between Disney World and Universal Orlando,” says David Myers, broker associate at Ziro Realty, who lives in the nearby Windermere area. “Residents enjoy quick access to the Butler Chain of Lakes.”
The Butler Chain of Lakes comprises 13 lakes and canals spanning 5,000 acres. Locals have plenty of options for enjoying the water, whether fishing from shore, enjoying a scenic boat ride, or bumping up the adrenaline with water sports like wakeboarding and water skiing. Avid golfers can enjoy the neighborhood's world-renowned Arnold Palmer’s Bay Hill Club and Lodge. This challenging 18-hole championship golf course makes for an exciting day on the green. Continuing the legacy of its namesake golf legend, the Bay Hill Club hosts the annual Arnold Palmer Invitational each March. Here, the best professional golfers compete for the coveted champion title, and residents come out to enjoy a weekend of golf and celebrity. Members can dock their boats at the marina, stay at the 70-room Lodge, play tennis, or relax and unwind at the spa.
Homes range from ranch-style to more grandeur estates on the Butler Chain of Lakes. Because the majority of these houses were built in the 1970s and 1980s, residents live in a community where each home has a unique charm. Homeowners in this area also enjoy the privilege of living on larger lots that typically range from a half-acre to several acres. “Residents benefit from quick access to the Butler Chain of Lakes,” Meyers says. According to him, homes built closer to the Butler Chain of Lakes usually start at $1 million. Larger homes near the water can range in price from $1 million to over $3 million. Homes perched further away from the lakes can range from $500,000 to $800,000.
Residents of Bay Hill dine at the famous Restaurant Row on Sand Lake Road. Myers recommends the popular Rocco’s Tacos, which offers great Mexican fare and over 200 varieties of tequila in a casual atmosphere. He also recommends Ocean Prime, famous for its seafood and steak. For private dining, there is London House, a lifestyle and social club that offers a world-class dining experience. Restaurant Row is also home to many cigar bars and steakhouses. For groceries, Trader Joe’s and Whole Foods are located just east of the neighborhood, within a few miles' drive. Big box stores and other retailers, such as Walmart and Ross Dress for Less, can be found all along the nearby Interstate 4.
The Bay Hill community is served by three elementary schools, two middle schools and one high school. Students in the neighborhood can attend Dr. Phillips Elementary, which receives an overall grade of A-minus from Niche. Southwest Middle earns a B, and Dr. Phillips High receives an A-minus. Dr. Phillips High is home to two magnet school programs: The Center for International Studies and The Visual & Performing Arts program.
Bay Hill is less than a 25-minute drive from Downtown Orlando. Most locals commute by car, but Central Florida’s LYNX bus lines also service the area. A sunny community packed with amenities – this is Bay Hill.
Property Mix - Square Feet
Windermere Has More Owners
Demographics
Total Population
2,921
Median Age
48
Population under 18
21%
On par with the national average
23.8%
Population over 65
23.3%
On par with the national average
19.1%
Finances
Median Household Income
$141,029
Significantly above the national average
$71,702
Average Household Income
$166,975
Education and Workforce
High School Graduates
98.1%
College Graduates
66.3%
Significantly above the national average
34.1%
Advanced Degrees
25.3%
Above the national average
13.3%
% Population in Labor Force
63.7%
Weather
Annual Precipitation
52''
Average Winter Low Temperature
47°F
Average Summer High Temperature
92°F
Annual Snowfall
0''
Area Factors
Somewhat Bikeable
Bike Score®®
38/ 100
Car-Dependent
Walk Score®®
27/ 100
Source: Walk Score
Source: Walk Score
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
