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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11900 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all
$18,500,000
7Bedroom(s)
9Bathroom(s)
10,649Sqft

4226 Downeast Ln, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Exceptional DEVELOPMENT OPPORTUNITY,R-CE zoning may allow for 2 Lakefront Luxury Home Sites + Additional Lots on these two parcels. Discover over 9 acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, part of the coveted BUTLER CHAIN of Lakes.
$14,800,000
5Bedroom(s)
3Bathroom(s)
OversizedParking(s)
5,316Sqft

5525 Isleworth Country Club Dr, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world.
$14,250,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
9,511Sqft

9621 Windy Ridge Rd, Windermere, Florida 34786

Residential For Sale

CITARELLI REALTY GROUP LLC
Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.
$13,700,000
9Bedroom(s)
16Bathroom(s)
20,445Sqft

9935 Lake Louise Dr, Windermere, Florida 34786

Residential For Sale

IRWIN REALTY GROUP LLC
Under contract-accepting backup offers. Experience the pinnacle of luxury living in this extraordinary lakefront estate located in the world-renowned Isleworth Golf & Country Club. Positioned on 2.
$12,995,000
7Bedroom(s)
10Bathroom(s)
Garage Door OpenerParking(s)
16,257Sqft

4200 Down Point Lane, Windermere, Florida 34786

Residential For Sale

REVEL REALTY LLC
Nestled along almost 1,000’ of the highly sought after Butler Chain of Lakes in Windermere, this exquisite Mediterranean estate beckons with unrivaled opulence. Beyond a private gate, a 2-acre peninsula reveals a masterpiece of architectural brilliance designed by Nasrallah and built by Ray Coudriet.
$10,900,000
6Bedroom(s)
9Bathroom(s)
Garage Door OpenerParking(s)
14,435Sqft

6149 Grosvenor Shore Dr, Windermere, Florida 34786

Residential For Sale

SOUTHERN REALTY GROUP LLC
Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside.
$9,999,000
6Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
6,783Sqft

6137 Grosvenor Shore Dr, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBY'S INTL. REALTY
Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sought-after Windermere.
$9,500,000
6Bedroom(s)
9Bathroom(s)
Garage Door OpenerParking(s)
9,571Sqft

9343 Tibet Pointe Cir, Windermere, Florida 34786

Residential For Sale

LA ROSA REALTY LLC
PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry.
$8,250,000
7Bedroom(s)
10Bathroom(s)
OversizedParking(s)
8,362Sqft

5074 Isleworth Country Club Dr, Windermere, Florida 34786

Residential For Sale

MEMARPOURI REALTY LLC
Experience luxury living at its finest in the high end gated community of Isleworth. Nestled on the 6th fairway of Isleworth’s world-renowned golf course, this beautifully redesigned estate offers over 6,900 square feet of exquisite living space, featuring 5 bedrooms and 6.5 bathrooms.
$7,995,000
5Bedroom(s)
7Bathroom(s)
6,937Sqft

6507 Rosella Ct, Windermere, Florida 34786

Residential For Sale

DEANNA MARIE SECHREST
Luxury Living at its finest in one of Windermere's most unique Waterfront properties, with 2+ acres in the exclusive Keene's Pointe community. Soak up the Florida sunshine in the very private garden oasis boasting 2 Resort Style pools with waterfalls, grotto and waterslide, outdoor kitchen and fireplace all overlooking Lake Tibet on the Butler Chain of Lakes.
$7,750,000
7Bedroom(s)
8Bathroom(s)
10,485Sqft

9349 Tibet Pointe Cir, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Set along the pristine shores of Lake Tibet Butler, this remarkable Keene’s Pointe estate is a showpiece of enduring craftsmanship and thoughtful design. Every element of its 7,500+ sq ft reflects meticulous attention to detail and a level of care that defines timeless luxury living.
$6,970,000
5Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
7,529Sqft
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