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
Justin Hess,
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 55 days. The median sale price for homes in Windermere, FL over the last 12 months is $835,000, up 1% from the median home sale price over the previous 12 months.
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,
Welcome to Merrick Landing, a highly desirable Windermere community offering comfort, convenience, and a touch of magic. This rare ONE STORY, well appointed townhome features a primary bedroom with a Private Ensuite. The Open concept kitchen boasts stainless steel appliances and overlooks the spacious living area, making it perfect for both everyday living and entertaining. Enjoy slate flooring
Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As
**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
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
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
**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
**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 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community. This home offers a bright open floor plan with comfortable
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
CLOSING COST ASSISTANCE IF FINANCED WITH PREFERRED LENDER. Welcome to your private oasis in the prestigious, guard-gated community of Keene’s Pointe. Situated on one of the largest lots in the neighborhood, this exceptional fully furnished 5-bedroom, 4-bath residence offers breathtaking golf course views and an abundance of indoor and outdoor living space. Designed for both elegance and comfort,
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
Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in
Ideally situated within WINDERMERE LANDINGS and in close proximity to highly rated schools, convenience stores, restaurants, golf courses & other amenities, this IMMACULATELY presented 3 bedroom and 2.5 bath property with 2 car garage and private driveway is a true GEM with its stunning curb appeal and TURNKEY presentation! On approach the front porch feels inviting with its welcoming entryway
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
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
Live in one of the most sought after locations of Windermere! Welcome to 9313 Palm Tree Drive, located just minutes from Disney, Dr. Phillips, and Restaurant Row without the traffic and chaos. Located in the Silver Woods community off Apopka Vineland Rd, this 3 bedroom, 2 bath recently updated home is the perfect spot as your new home! Inside, you’ll find updated quartz countertops, newer
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.
Welcome to this beautiful townhouse in the highly desirable Summerport community of Windermere. Ideally situated near community amenities, this 2-story home offers a functional and inviting layout with 4 bedrooms, 2.5 bathrooms, a 2-car garage, and a primary suite on the main level. As you step inside, you’ll notice the open-concept design connecting the kitchen, dining, and living areas, all
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.
Beautiful house for rent in Windermere!! location, location and location. 3 bedrooms, 2 baths, 2 car garages. Beautiful large backyard and screen porch. Great school system. House is in highly desirable Lakes of Windermere! NO CARPETS!! The interior is FRESHLY Painted in alabaster tones, 3 Bedrooms, 2-baths, property is loaded with upgrades and has purposeful utility and functionality. Enter into
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
Location, location!!! Beautifully maintained home in highly desirable community of Providence! A rated schools, shops and restaurants are minutes away for your convenience. 4 bedroom 3 full bath home offers, additional office, formal dining area, private pool with spa and 3 car garage. Home has a NEW roof and AC installed in 2020, new water filter system and a pool heater. Open floor plan with
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.
AVAILABLE MAY 2026! Spacious 4-bedroom, 2.5-bath home in the desirable Lakes of Windermere community. This well-designed floor plan features all bedrooms upstairs, with the main floor offering a large living room, formal dining room, office/reading room, and a convenient half bath for guests. The primary suite includes dual vanities, a garden tub, and two large walk-in closets. The kitchen is
TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive
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