Windermere Florida Homes for Sale

Discover Windermere, Florida: Where Luxury Meets Lake Life

Welcome to Windermere, one of Central Florida’s most prestigious and picturesque communities. Nestled among pristine lakes and rolling hills just 20 minutes from downtown Orlando, Windermere offers an exclusive blend of natural beauty, top-rated schools, and small-town charm that’s increasingly rare in the Sunshine State.

Known for its stunning lakefront estates and tree-lined streets, Windermere has become the address of choice for professionals, families, and those seeking a refined Florida lifestyle. The town’s unique character is defined by its 21 sparkling lakes, including the expansive Butler Chain of Lakes, which provide residents with world-class boating, fishing, and watersports opportunities right in their backyard.

Award-Winning Education

Families are drawn to Windermere’s exceptional educational opportunities. The area is served by highly-rated Orange County Public Schools, including Windermere Elementary and Windermere High School, both consistently earning “A” ratings. The Windermere Preparatory School, a prestigious private institution, offers world-class education from pre-K through 12th grade with an international focus.

Community & Lifestyle

Despite its growth, Windermere maintains its welcoming community spirit. The town center features charming local shops, restaurants, and the beloved town of Windermere hosts regular events throughout the year, including seasonal festivals and the popular farmers market. Residents enjoy easy access to world-renowned theme parks, while the nearby Orange County Parks system offers countless outdoor recreation opportunities.

Whether you’re seeking a waterfront estate, a family-friendly neighborhood, or a luxury golf course community, Windermere delivers an unparalleled Central Florida living experience. At Holiday Realty Florida, we’re proud to help you find your perfect home in this exceptional lakeside paradise.

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5036 Latrobe Dr, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat.
$4,900,000
5Bedroom(s)
5Bathroom(s)
5,548Sqft

225 Magnolia St, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakes—a residence that redefines lakefront luxury in the exclusive town of Windermere.
$4,899,000
7Bedroom(s)
11Bathroom(s)
DrivewayParking(s)
5,935Sqft

12540 Park Ave, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated community of Chaine du Lac, this distinguished estate features timeless architecture paired with transitional interiors and gorgeous views to showcase Windermere lakefront living at its finest.
$4,650,000
5Bedroom(s)
6Bathroom(s)
OversizedParking(s)
7,183Sqft

5500 W Lake Butler Rd, Windermere, Florida 34786

Residential For Sale

JACK KELLER INC
Nestled on a 5-acre lot with 320 feet of lakefront and a private beach on the skiable Lake Davis. This Contemporary 8-bedroom, 6 full bath home wrapped with open porches spans nearly 7000 sq ft. Grand foyer with spiral staircase which features a magnificent glass wine cellar below. Modern, open concept with water views from nearly every room.
$4,299,999
8Bedroom(s)
6Bathroom(s)
Alley AccessParking(s)
7,000Sqft

9725 Chestnut Ridge Drive, Windermere, Florida 34786

Residential For Sale

HAMILTON REALTY
This exceptional custom built home is situated within the 600 acre exclusive Isleworth Golf and Country Club, you are surrounded by the pristine lakes of the Butler Chain - 12 inter-connected outstanding boating/water sport Lakes.
$4,299,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
6,885Sqft

801 W 2nd Ave, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBY'S INTL. REALTY
Experience the epitome of lakefront living on the Butler Chain of Lakes with this exceptional Windermere estate. On one of the area’s desirable streets, this home offers over $350,000 of recent luxurious upgrades, including a new kitchen and fireplace, new windows and doors, landscape lighting, new landscaping, a newly painted exterior and roof.
$4,250,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
5,639Sqft

11002 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

SERENDIPITY REALTY LLC
Under contract-accepting backup offers.
$4,200,000
5Bedroom(s)
8Bathroom(s)
OversizedParking(s)
6,248Sqft

12132 Montalcino Cir, Windermere, Florida 34786

Residential For Sale

BELLA VIEW REALTY LLC
Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.
$4,199,000
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
5,709Sqft

9648 Mccormick Pl, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout.
$3,800,000
3Bedroom(s)
4Bathroom(s)
4,751Sqft

10545 Down Lakeview Cir, Windermere, Florida 34786

Residential For Sale

COLONIALTOWN REALTY
Enjoy stunning sunsets from your private estate with expansive views, located on Lake Down, the prestigious Butler Chain of Lakes in Windermere. This well-appointed property features 2.78 acres with fully fenced terraced grounds, electric security gates, brick pavers, mature landscaping for privacy, and 130 feet of water frontage with a seawall, enclosed boat house, dock, and lift.
$3,795,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
7,263Sqft

12812 Jacob Grace Ct, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
Experience Unmatched Lakeside Luxury in a Custom-Built Masterpiece Discover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community.
$3,775,000
4Bedroom(s)
5Bathroom(s)
6,054Sqft

2844 Marquesas Ct, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmering waters of Lake Crescent. Nestled within the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece offers just under 6,000 square feet of newly remodeled, reimagined luxury living.
$3,700,000
4Bedroom(s)
3Bathroom(s)
Garage Faces SideParking(s)
5,365Sqft
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