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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11209 Macaw Ct, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
A Masterpiece on the 4th Hole – Keene’s Pointe Luxury Living Perfectly poised on a premium golf-front lot in the gorgeous, guard-gated community of Keene’s Pointe, this custom-built residence by Unnerstall blends refined craftsmanship with thoughtful design and breathtaking views of the Golden Bear Club’s 4th hole and tranquil water features.
$2,825,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,105Sqft

6120 Payne Stewart Dr, Windermere, Florida 34786

Residential For Sale

SOUTHERN REALTY GROUP LLC
Isleworth - nestled in Windermere, this 600-acre community, is a prestigious residential enclave nestled along the Butler Chain of Lakes. This charming villa is in walking distance to Isleworth Golf & Country Club.
$2,799,000
4Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,636Sqft

1821 Windermere Rd, Windermere, Florida 34786

Residential For Sale

ORLANDO TBI REALTY LLC
Under contract-accepting backup offers. Pre-Construction. To be built. Discover an unparalleled opportunity to acquire a sovereign 1.16-acre estate homesite in the heart of Windermere. This meticulously positioned property, oriented east-west for optimal light, is ensconced within a private setting and borders a permanent conservation area, ensuring absolute privacy and serene, unimpeded vistas.
$2,756,995
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,996Sqft

9648 Weatherstone, Windermere, Florida 34786

Residential For Sale

ERA GRIZZARD REAL ESTATE
Welcome to this exceptional lakefront estate in the exclusive gated community of Weatherstone, ideally situated on the serene shores of Lake Olivia in Windermere, Florida. This beautifully appointed residence offers 7 bedrooms, 4 full bathrooms & a rare combination of timeless architecture & modern luxury. From the moment you arrive, the home's curb appeal is undeniable.
$2,725,000
7Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,482Sqft

9905 Lanai View Ct, Windermere, Florida 34786

Residential For Sale

MAXIM REALTY ORLANDO
BACK ON THE MARKET - BUYERS' FINANCE FELL THROUGH. Welcome to a home that isn’t just designed—it’s curated. Tucked behind the gates of one of Central Florida’s most exclusive golf communities, 9905 Lanai View Court is the kind of estate that makes you pause.
$2,650,000
5Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
7,621Sqft

8402 Lake Burden Cir, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
One or more photo(s) has been virtually staged. Newly added virtually staged images to help with your interior design inspiration! Experience luxury waterfront living in the prestigious guard gated community of Keene's Pointe. This custom estate offers over 6,000 sq ft of elegant living space with 5-bedroom ensuites and a full pool bath with shower and powder room off of the Theater.
$2,650,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,248Sqft

6102 S Hampshire Ct, Windermere, Florida 34786

Residential For Sale

CHARLES RUTENBERG REALTY ORLANDO
This elegant single-story Rick Watson home, located at 6102 S Hampshire Court, Windermere, FL 34786, sits on a private Jack Nicklaus–designed golf course lot in the exclusive, 24-hour manned and gated community of Keene’s Pointe. Enjoy uninterrupted views of the 6th hole by day and Disney Fireworks at night from key living areas and the outdoor lanai.
$2,650,000
4Bedroom(s)
6Bathroom(s)
Converted GarageParking(s)
4,810Sqft

12030 Waterstone Loop Dr, Windermere, Florida 34786

Residential For Sale

GRANDE REALTY GROUP LLC
Tropical paradise in Windermere this 5+ bedroom dream home in the high-end community of Waterstone. Spanning over 6500 SF, this magnificent pool residence graced by soaring ceilings and a tranquil lake view. The grand entryway with two sweeping staircases draws you into a voluminous layout made for entertaining.
$2,600,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,853Sqft

1724 Windermeredown Pl, Windermere, Florida 34786

Residential For Sale

SERHANT
Private Resort Luxury with Butler Chain Access in Windermere Downs Set within one of Windermere’s most sought-after lakefront communities, this extraordinary residence offers exclusive access to the Butler Chain of Lakes.
$2,500,000
6Bedroom(s)
7Bathroom(s)
Circular DrivewayParking(s)
6,000Sqft

11113 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

QUATTRO R E SOLUTIONS LLC
Welcome to this beautiful, unique and modern home, built less than 3 years ago.
$2,499,000
5Bedroom(s)
6Bathroom(s)
4,094Sqft

11019 Ullswater Ln, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Under contract-accepting backup offers. Welcome to 11019 Ullswater Drive, a timeless Italian-inspired residence built by Brierhill Custom Homes. Set on over half an acre within the 24-hour manned gates of The Reserve at Lake Butler Sound, this home offers exceptional updates, modern amenities, and a thoughtfully designed floor plan.
$2,495,000
5Bedroom(s)
5Bathroom(s)
5,916Sqft

11106 Coniston Way, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Under contract-accepting backup offers. A one-of-a-kind French Provincial estate, "The Monet," was crafted by Master Custom Builder Castleworks in 2008 and has been updated a smart home for today’s buyers.
$2,450,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
5,934Sqft
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