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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13448 Bellaria Cir, Windermere, Florida 34786

Residential For Sale

KENNEDY REALTY GROUP LLC
Under contract-accepting backup offers. This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting the elegant handcrafted staircase in the foyer.
$3,250,000
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,308Sqft

4711 Joanna Garden Ct, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally designed interiors, the single-story home seamlessly blends architectural sophistication with inviting comfort.
$3,250,000
3Bedroom(s)
4Bathroom(s)
4,089Sqft

6186 Louise Cove Drive, Windermere, Florida 34786

Residential For Sale

THE SIMON SIMAAN GROUP
A Masterpiece of Design in Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.
$3,250,000
4Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
4,849Sqft

5067 Sawyer Cove Way, Windermere, Florida 34786

Residential For Sale

REVEL REALTY LLC
STUNNING CUSTOM estate in the exclusive GATED community of Sawyer Sound - a private enclave of just 20 luxury homes, ideally located near top-rated public and private schools, excellent dining, and premiere entertainment. Built under the meticulous supervision of its owners, one of whom is an accomplished interior designer, this home showcases exceptional quality and attention to detail.
$3,200,000
5Bedroom(s)
4Bathroom(s)
3,461Sqft

4819 Alexandra Garden Ct, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa.  Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining.
$3,200,000
4Bedroom(s)
5Bathroom(s)
3,745Sqft

13161 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

EPIQUE REALTY, INC.
Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room.
$3,200,000
5Bedroom(s)
5Bathroom(s)
4,500Sqft

2 Chase Rd, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance.
$3,200,000
4Bedroom(s)
5Bathroom(s)
3,889Sqft

12720 Jacob Grace Ct, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Tucked inside one of Windermere’s most exclusive guard-gated communities, this extraordinary custom-built estate is more than a home — it’s a destination. With almost 6000sq. ft., six bedrooms, six and a half baths, a detached in-law suite, and nearly two acres of pristine lakefront land, it represents the pinnacle of Central Florida luxury.
$2,999,999
6Bedroom(s)
7Bathroom(s)
5,882Sqft

12923 Water Point Blvd, Windermere, Florida 34786

Residential For Sale

LAKESIDE REALTY WINDERMERE INC
Welcome to 12923 Water Point Blvd., a stunning lakefront estate nestled in the exclusive, man-guard gated community of Waterford Pointe in Windermere. This impressive residence offers over 5,000 square feet of luxurious living space with 4 bedrooms in the main home, including a spacious primary suite conveniently located on the first floor.
$2,999,999
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
5,005Sqft

2828 Marquesas Ct, Windermere, Florida 34786

Residential For Sale

DALTON WADE INC
Gorgeous Private Lakefront Custom Brick Estate over 10,000 sq ft under roof, just under 7,000 sq ft under HVAC. First Time Ever on Market! Step thru the Gorgeous Leaded Glass Doors into this Magnificent Estate the Entry made for Royalty Custom Magnolia Curved Staircase with custom Italian Marble Flooring installed 2024. Updated Massive Chandler with Sconces lighting grace the Staircase.
$2,995,000
6Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
6,819Sqft

6219 Tiroco Way, Windermere, Florida 34786

Residential For Sale

CENTURY 21 CARIOTI
Welcome to luxury living in the guarded gated community of Waterstone in Windermere, Florida. This exquisite residence at 6219 Tiroco Way offers unparalleled elegance and modern comfort featuring Solar power. The home offers 7 bedrooms, 5 ½ baths, a media room, a loft, a storage room, separate formal rooms, and a dedicated office.
$2,900,000
7Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,221Sqft

4047 Isabella Cir, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Under contract-accepting backup offers. $75,000 credit towards pool with acceptable offer! This exceptional 2019-built home has been transformed with nearly a full interior remodel, making it one of the most distinctive properties in the sought-after Windermere community of Casabella. As the largest model in the neighborhood, this home offers a rare blend of space, style, and function.
$2,850,000
6Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
8,372Sqft
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