Windermere is a charming Old Florida town on the Butler Chain of Lakes
Windermere was once a vacation destination for affluent retirees, drawn to the small town’s Old Florida charm and elegant homes overlooking the Butler Chain of Lakes. The town celebrated its centennial in 2025, and the resort-like atmosphere is much the same today as it was in the 1920s. Spindly loblolly pines and live oaks draped with Spanish moss shade quiet, walkable streets lined with historic and vintage-inspired architecture. “You always see people out riding their bikes and walking their dogs,” says Toni Marie Cafferty, a Compass Florida real estate advisor who sells throughout Central Florida. “Our schools are A-rated, and the community has a lot of family-friendly events, which I think is a big draw,” she says. Proximity to Orlando, less than 15 miles away, adds to the appeal.
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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Isleworth and other subdivisions feature high-end homes and lake views
The town is made up of multiple subdivisions, many of which are gated. Monthly HOA fees run anywhere from under $100 to over $1,000. Isleworth is a standout community of sprawling, multi-million-dollar Mediterranean and French Provincial-style estates, with meticulous landscaping and lake views. Some of Windermere’s most famous residents, including Tiger Woods and Shaquille O’Neal, have lived in Isleworth. Other developments, like Lake Down Cove, Keene’s Pointe, Lake Butler Sound and Waterstone on Lake Butler, feature Colonial Revivals, New Traditionals and Contemporary homes. Townhomes and condos are available in the Lake Burden and the Lakes of Windermere communities.
Single-family home prices range from about $540,000 to $9 million, depending on size, subdivision and view. Large, custom-built homes with private lake access typically sell for $1.7 million and up. Townhome prices start around $345,000 and rise to about $560,000. Condos usually range between $285,000 and $340,000. Windermere’s median of $850,000 is higher than the Orange County median of about $450,000 reported by the National Association of Realtors.
Flooding and wind damage are risks during hurricane season, and Orange County is moderately vulnerable to tornadoes.
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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Kids attend highly rated Orange County Public Schools
Orange County Public Schools earns a B-plus from Niche and allows school transfers by application. Kids may attend Windermere Elementary (A), Bridgewater Middle (A-minus) and Windermere High (A-plus), which offers dual-credit classes at Orange Technical College. Windermere Preparatory Academy is a private, A-plus-rated college prep school for prekindergarten through 12th grade.
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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Windermere Recreation Center, Town Square Park and more amenities
Windermere Recreation Center, also known as Butler Bay, has a fenced-in playground with wheelchair access, covered picnic tables and a sand volleyball court. It also has a kayak launch on Lake Crescent and a boardwalk trail over the water. The tennis courts at the rec center, and those at the Park Among the Lakes nearby, are resident-only. Passes may be purchased at the town hall, near the Windermere Branch library. Other parks in the area, including Palmer Park and Central Park, have playgrounds, exercise equipment and more. Private clubs nearby, such as Isleworth Golf & Country Club and The Golden Bear Club at Keene’s Point, have golf courses, swimming pools, tennis courts and other amenities.
Every winter, the town hall hosts the Windermere Wine & Dine event, which showcases samplings of dishes and drinks from local restaurants. Town Square Park, nearby, hosts the town’s annual 4th of July Pancake Breakfast, Halloween Hayride & Costume Parade and Windermere PetFest. The green space also hosts Food Truck Nights and the weekly Windermere Farmer’s Market.
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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Main Street shopping/dining, Dr. Phillips Restaurant Row nearby
Main Street is lined with locally owned shops and restaurants. Tim’s Wine Market and Windermere Fine Art & Custom Framing are close to Pistil, a home décor and garden shop. The nearby Windermere Brewing Company taproom is popular for craft beer, trivia competitions and live music nights. The Grove shopping center, off Conroy Windermere Road, has a Publix and a Walgreens and various dining options, including Island Fin Poké and BurgerFi. Windermere is also close to Restaurant Row, a stretch of Sand Lake Road in the neighboring Doctor Phillips community known for its wide variety of eateries.
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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Close to theme parks, hospitals, Orlando International Airport
Major Orlando attractions, including Disney World, Universal Studios and SeaWorld, are within about 15 miles of most homes. Two large hospitals, the Orlando Health Regional Medical Center and Orlando Health Dr. P. Phillips Hospital, are also less than 15 miles from most homes. Orlando International Airport is roughly 25 miles away via Florida’s Turnpike and State Road 528.
Written By
Megan Quintin
Photography Contributed By
Jeffery Palmer
Video By
Scott Wiggins
Interested in learning more about homes in this area?
Reach out to
Will LaValle,
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 72 days on the market compared to the national average of 53 days. The median sale price for homes in Windermere, FL over the last 12 months is $875,000, up 11% from the median home sale price over the previous 12 months.
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8632 Abbotsbury Drive, a beautifully situated 4-bedroom, 3.5-bath residence offering 2,720 square feet of heated living space in the heart of Windermere, one of Central Florida’s most desirable communities. This
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering
LUXURY WINDERMERE HOME ON OVERSIZED CONSERVATION LOT - Welcome to Windermere living at its finest! This beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Vineyards of Horizon West community offers modern design, a private conservation view, and top-rated Windermere schools - all under $700K. Step inside to discover a spacious open-concept floor plan featuring acacia
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8632 Abbotsbury Drive, a beautifully situated 4-bedroom, 3.5-bath residence offering 2,720 square feet of heated living space in the heart of Windermere, one of Central Florida’s most desirable communities. This
Spectacular Windermere Home WITH LUXURIOUS IN-LAW SUITE! Freshly painted, and brand new luxury vinyl floors. 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
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
WELCOME HOME TO TO THIS SPACIOUS, BEAUTIFUL 2 STOREY HOME IN ONE OF ORLANDO'S MOST SOUGHT AFTER COMMUNITIES, "THE WINDERMERE CLUB'.THIS HOME SITS ON OVER AN ACRE OF PROPERTY AND IS SURROUNDED BY FLORIDA'S GORGEOUS NATURAL LANDSCAPE. PRIVACY, PRIVACY PRIVACY IN THIS BEAUTIFUL HOME. FROM THE MOMENT YOU ARRIVE HOME, YOU WILL BE GREETED BY THE EXPANSIVE DRIVEWAY AND THE GRANDUR OF THIS CUSTOM HOME'S
The house has 4 Bedrooms and three and a half bath rooms, two of them are ensuite bedrooms with walk in closets and master bathrooms with double vanity. There IS another very big bonus room with bath room and walking closet on top of the garage. Which can be used as a bedroom or an office . In this way this house has 5 bedrooms and 4.5 bathrooms. Open floor concept. The kitchen includes an island
Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay
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