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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9259 Tibet Pointe Cir, Windermere, Florida 34786

Residential For Sale

SOUTHERN REALTY GROUP LLC
Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet.
$6,800,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
6,257Sqft

11103 Bridge House Rd, Windermere, Florida 34786

Residential For Sale

THE SIMON SIMAAN GROUP
Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man-gated community of Lake Butler Sound—one of Central Florida’s most prestigious communities. From the moment you enter, you're greeted by high-end finishes, open-concept living space, and meticulous attention to detail.
$6,799,000
5Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
8,443Sqft

9639 Westover Roberts Rd, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking.
$6,395,000
5Bedroom(s)
9Bathroom(s)
11,861Sqft

9826 Laurel Valley Dr, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds across a premium homesite on the shores of Lake Butler, where the water is clear, the sandy beach is pristine, and the sunsets spill across the horizon in dazzling color every evening.
$5,900,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
7,491Sqft

12264 Montalcino Cir, Windermere, Florida 34786

Residential For Sale

WRA BUSINESS & REAL ESTATE
Lakefront, Luxurious, Fully Furnished Home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere, located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views.
$5,860,000
4Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
7,872Sqft

1003 Down Reserve Ct, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Welcome to a rare modern estate inside an intimate gated enclave, offering 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.
$5,499,999
6Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
6,816Sqft

5199 Latrobe Dr, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
One or more photo(s) has been virtually staged. Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you are sure to fall in love with.
$5,494,000
5Bedroom(s)
7Bathroom(s)
4,665Sqft

9721 Carillon Park Dr, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
Welcome to 9721 Carillon Park Dr, Windermere, FL 34786 - a stunning FULLY FURNISHED (furniture included-with exception of a few items) , professionally designed estate inside the guard-gated community of Keene’s Pointe. This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout.
$5,489,000
6Bedroom(s)
9Bathroom(s)
Garage Door OpenerParking(s)
8,305Sqft

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)
Garage Door OpenerParking(s)
7,600Sqft

4089 Isabella Cir, Windermere, Florida 34786

Residential For Sale

NOVA REAL ESTATE SERVICES INC
Welcome to 4089 Isabella Cir. A Home Like No Other, Exquisite Custom Luxury in Casabella, Windermere, FL Step into unparalleled luxury with this completely reimagined six-bedroom, six-bathroom estate in the prestigious Casabella community of Windermere. Every inch of this home has been custom-curated with the finest materials and designer touches, creating an ambiance of modern sophistication.
$5,000,000
6Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
6,855Sqft

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)
Garage Door OpenerParking(s)
8,931Sqft
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