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
Emily Armstrong,
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 74 days on the market compared to the national average of 54 days. The median sale price for homes in Windermere, FL over the last 12 months is $840,000, up 3% from the median home sale price over the previous 12 months.
Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much
Freshly painted interior 4-bedroom home in a gated Windermere community — less than one mile from Windermere Preparatory School.Located in the exclusive Enclave at Glenmuir, this beautifully maintained 4-bed, 2-bath residence sits on a quiet cul-de-sac with tranquil water views, offering privacy, comfort, and an unbeatable price point for the area. Inside, a bright, open floor plan connects
One or more photo(s) has been virtually staged. *Images shown are for illustrative purposes only* TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also
Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a
**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
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
**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
The coveted Keene's Pointe lifestyle awaits behind the guarded gates of this world renowned golf community. Perfectly positioned near the tranquil shores of Lake Burden, this Mediterranean-inspired estate and it’s stunning architecture captures the eye and invites you to a front-row seat to the nightly water front display of Walt Disney World fireworks. This custom-built residence showcases
**Sellers are offering a 5.5% INTERESTED RATE** Luxury Windermere Home for Sale in Gated Community with New Roof & Windows!Welcome to this stunning 4-bedroom, 3-bathroom home in a sought-after gated Windermere community, offering nearly 3,000 square feet of beautifully designed living space, a 3-car garage, NEW ROOF and NEW WINDOWS. Enjoy nightly Walt Disney World firework views from the
Back on market—buyer withdrew for personal reasons, not due to any home-related issues.Set on 1.3 acres in the Lake Buynak Estate community, this 4-bedroom, 3.5-bath home presents an outstanding opportunity for investors, builders, or buyers wanting space and a Windermere-area address with NO HOA. Offering over 2,600 square feet, two ensuite bedrooms, a split layout, multiple screened
Welcome to the Arlington with Bonus! This stunning 3,123 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio,
Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove,
Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable
LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Windermere. This exceptional vacant homesite offers over 2.12 acres and is the largest buildable lot within this private gated enclave of only four estate properties, providing exceptional privacy and generous spacing between homes. The
Enjoy over $35,000 in upgrades in this beautiful Windermere subdivision! This CORNER LOT home is move-in ready with FRESH INTERIOR AND EXTERIOR PAINT * REPLACED CARPETING * RENOVATED SECOND BATHROOM SHOWER * KITCHEN QUARTZ COUNTERTOP * APPLIANCES REPLACED * WASHER AND DRYER INLUDED * WATER SOFTENER/FILTRATION SYSTEM and more! Experience the bright and inviting atmosphere from the moment you
Welcome to an end-unit townhome in the highly desirable Lakes of Windermere – Lake Reams Townhomes community. Located in the Windermere area near Disney, this home offers a truly special perk—enjoy evening views of Disney fireworks right from the bedroom and backyard. The first floor features a bright, open-concept layout where large windows fill the living, dining, and kitchen areas with natural
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
Welcome to this gorgeous home in the prestigious gated community of Lake Davis Reserve. This spacious residence features five bedrooms, including two master suites one conveniently located on the first floor and another on the second floor offering comfort and flexibility for families of all sizes.The kitchen blends traditional charm with modern design, providing plenty of space for cooking
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
Spacious 3-bedroom, 2-bath condominium located on the 2nd floor of a well-maintained community in highly desirable Windermere, FL. This 1,455 sq ft unit offers an open and functional floor plan featuring a large living/dining area, generous natural light, and a well-appointed kitchen with ample cabinetry and counter space. The primary suite includes a walk-in closet and a private bath. Secondary
A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication youll find awe-inspiring day and night.
Stunning 3-Bed, 2.5-Bath End Unit Townhouse in Lakes of Windermere – Lake Reams! Enjoy a spacious, sun-filled layout, a sleek kitchen with appliances, and a detached 2-car garage. Perfectly located for easy access to Orlando, yet tucked away in a peaceful, welcoming neighborhood. Shopping, dining, and entertainment are just minutes away! Don’t wait—this gorgeous home won’t last long. Schedule
Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.
Beautifully renovated 3-bedroom townhome with a flex room located in the highly desirable Windermere Trails community. This bright and inviting home features 3 bedrooms, 2.5 bathrooms, and a versatile flex room on the first floor, perfect for a home office, playroom, or additional living space.The open-concept floor plan seamlessly connects the living and dining areas to a spacious family
Enjoy a vibrant lifestyle at Arya at Windermere, a 55+ community in Ocoee, FL offering unparalleled luxury amenities, including a massage room, steam room, outdoor putting green and a micro market. Arya features open concept 1 and 2-bedroom apartments with chef-inspired kitchens, granite countertops, stainless steel appliances, breakfast bar, wood-style plank floors, walk-in shower, washer and
Beautiful 4-bedroom, 2.5-bath townhome located in the highly desirable Windermere Sound community in Horizon West. Built in 2015, this home offers approximately 1,997 sq ft of living space with an open floor plan ideal for everyday living and entertaining.The main level features a spacious living and dining area connected to the kitchen, while the primary bedroom provides comfort and privacy.
TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Discover resort-style living at MAA Crosswater in Windermere, FL. Garden tubs, double vanity sinks, and washer/dryer units are featured in these one-, two-, and three-bedroom apartment homes. Admire the lake view from our sparkling swimming pool and cabana, or dig your toes in the sand \"beach\" lounging area.
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