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.
1/4
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.
1/4
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.
1/2
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.
1/4
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.
1/4
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
Tiffany Pantozzi,
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 74 days on the market compared to the national average of 58 days. The median sale price for homes in Windermere, FL over the last 12 months is $835,000, consistent with the median home sale price over the previous 12 months.
Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2018), a/c (2016), plumbing, flooring, drain field
One or more photo(s) has been virtually staged. Under Construction. Sample Image Arlington Floorplan – 2,740 Sq. Ft. | 4 Beds | 3 Baths | 2.5-Car Garage a thoughtfully designed, 1-story home by Dream Finders Homes that perfectly blends luxury, functionality, and comfort. This brand new 2,740 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space, ready for
One or more photo(s) has been virtually staged. Arlington Floorplan – 3,140 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for
Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques,
Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable.
Welcome to 8409 Vivaro Isle Way, an exceptional move-in ready luxury residence located in the highly desirable community of Windermere Isle in Windermere. This impressive home offers 4,176 square feet of living space featuring 6 bedrooms, 4.5 bathrooms, and a dedicated office space. Perfectly positioned approximately 2.5 miles from Magic Kingdom Park at Walt Disney World Resort, this elegant home
Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 square feet of well designed living space, plus a 3 car garage and no rear neighbor as it backs to the brick wall of Windermere Terrace. Inside you'll find soaring 10' ceilings & 6-incht baseboards throughout, crown moldings in the family/kitchen area, ceramic tile in the kitchen & bathrooms and engineered wood
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
Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2018), a/c (2016), plumbing, flooring, drain field
A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a
Welcome to one of Windermere's most sought-after gated communities — where luxury living meets unbeatable Central Florida convenience. This impeccably maintained 4-bedroom, 3-bathroom home offers nearly 3,000 square feet of thoughtfully designed living space, a 3-car garage, and a brand-new roof and windows, giving buyers peace of mind and long-term value from day one.DISNEY VIEWS & OUTDOOR
Welcome to 2509 Ridgewind Way, a timeless Southern estate tucked inside the gates of The Estates at Windermere—one of Windermere’s most beloved communities known for its oak-lined streets, oversized lots, and quiet charm. Set on a rare .75-acre homesite, this beautifully updated residence blends classic architecture with the functionality today’s buyers are searching for. A wraparound front
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 one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent
Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. 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
Looking for seclusion? One plus acre waterfront. No HOA. Adorable, clean available June 1st. Bring your boat, RV, pets. Quiet treed drive located near the Town of Windermere. Complete with stainless appliances, washer, dryer. Large screened porch. Tile floors throughout. Decorative fireplace in family room. Room to Breathe!! Check it out today. For Application:
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
Beautiful ground floor unit in the Lakes of Windermere! This unit features 2 bedrooms, 2 bathrooms, ceramic tile flooring throughout and elegant crown molding in the living areas. The kitchen is complete with granite countertops, a breakfast bar and pantry. There is a separate dining area and living room that leads to the large screened in porch. The split floor plan allows privacy, and each
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.
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.
Discover refined active adult living at Arya at Windermere, a premier 55+ community offering luxury and vibrancy of Windermere. Our spacious one- and two-bedroom residences feature impressive finishes and thoughtful designs that elevate everyday living. Residents enjoy resort-style amenities including a massage room, steam room, and a host of social and wellness opportunities in a pet-friendly
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.
Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind
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
Property Id: 1359664Move-in ready townhome in Summerport. Well sought out location. Right by Publix, Aldi, Windermere High School. Freshly painted with updated flooring all around, no carpet.Move-in as soon as Feb 1st.There is appliances but no dishwasher.
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3154.90. That covers your base rent, $3010.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 4.0-bedroom, 3.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and
Local Logic measures the walkability, access to public transit and 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.
