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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6117 Louise Cove Dr, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Nestled along the shores of Lake Louise within Isleworth West, this exceptional two-story estate represents the finest in lakefront living. Offering four bedrooms, four-and-a-half baths, and more than 5,700 square feet of living space, the residence has been fully reimagined with sophisticated, modern finishes throughout.
$5,400,000
4Bedroom(s)
5Bathroom(s)
5,752Sqft

5243 Isleworth Country Club Dr, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas.
$5,325,000
4Bedroom(s)
6Bathroom(s)
Circular DrivewayParking(s)
6,424Sqft

9733 Carillon Park Dr, Windermere, Florida 34786

Residential For Sale

LAKESIDE REALTY WINDERMERE INC
Redefine luxury living. Welcome home to an exceptional lifestyle with an estate that offers impeccable design and unparalleled sophistication in one of Central Florida's most desirable guard-gated communities, Keene's Pointe. This masterfully designed residence, which was fully reimagined and painstakingly renovated over 2 years, blends modern luxury with timeless elegance.
$5,250,000
5Bedroom(s)
7Bathroom(s)
DrivewayParking(s)
7,600Sqft

1003 Down Reserve Ct, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Welcome to a rare modern estate in an intimate gated enclave. Imagine 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom-built masterpiece was designed for those who value privacy, prestige and perfection.
$4,999,999
6Bedroom(s)
8Bathroom(s)
DrivewayParking(s)
6,816Sqft

11618 Vinci Dr, Windermere, Florida 34786

Residential For Sale

WEMERT GROUP REALTY LLC
Behind the gates of Keene's Pointe, on the pristine shores of Lake Burden, an extraordinary lakefront estate awaits where modern design, curated luxury, and a truly magical setting come together in perfect harmony! Vinci Drive is a custom-built, fully furnished, turnkey masterpiece offering over 6,000 square feet of refined living on a desirable 1.16 acre lakefront lot.
$4,950,000
5Bedroom(s)
7Bathroom(s)
DrivewayParking(s)
6,188Sqft

9575 Westover Roberts Rd, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5.
$4,925,000
7Bedroom(s)
8Bathroom(s)
DrivewayParking(s)
8,931Sqft

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

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

6109 Orta Ct, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level.
$4,495,000
5Bedroom(s)
7Bathroom(s)
DrivewayParking(s)
5,895Sqft

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)
DrivewayParking(s)
6,885Sqft

11002 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

SERENDIPITY REALTY LLC
Back on the Market! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relax
$4,200,000
5Bedroom(s)
8Bathroom(s)
OversizedParking(s)
6,248Sqft

5050 Isleworth Country Club Dr, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
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.
$3,975,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
3,365Sqft
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