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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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)
DrivewayParking(s)
4,482Sqft

3103 Seigneury Dr, Windermere, Florida 34786

Residential For Sale

NEW SOLUTIONS REALTY INC
Stunning 8BR/5BA Renovated Estate in Exclusive Windermere Community Beautifully updated 7-bedroom, 5-bathroom home located in one of Windermere’s most exclusive neighborhoods, known for its quiet setting and top-rated schools.
$2,700,000
8Bedroom(s)
6Bathroom(s)
5,607Sqft

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)
DrivewayParking(s)
6,248Sqft

6288 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Golfers, entertainers, and chefs- this is the home that checks every box. Perfectly positioned on the 18th tee box of the Golden Bear Golf & Country Club, this move-in ready, three-story five-bedroom, four full and three half bath custom residence is one of the most unique properties in all of Keene’s Pointe.
$2,600,000
5Bedroom(s)
7Bathroom(s)
5,366Sqft

81 Oakdale St, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living.
$2,500,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,284Sqft

6102 S Hampshire Ct, Windermere, Florida 34786

Residential For Sale

CHARLES RUTENBERG REALTY ORLANDO
PRICE REDUCED $150K 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.
$2,499,000
4Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
4,810Sqft

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 across the street from Windermere Prep, and close to excellent dining, and premiere entertainment.
$2,490,000
5Bedroom(s)
4Bathroom(s)
3,461Sqft

9204 Tibet Pointe Cir, Windermere, Florida 34786

Residential For Sale

THE SIMON SIMAAN GROUP
Your stunning Keene’s Pointe custom home by Stonebridge was built for luxurious everyday living and effortless entertaining. The grand first floor features travertine and hardwood floors throughout, a formal living room with gas fireplace and stone mantle, elegant dining room with adjoining dry bar, and a private office with French doors.
$2,450,000
5Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
5,291Sqft

11113 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

QUATTRO R E SOLUTIONS LLC
Welcome to this beautiful, unique and modern home. Recently built in 2023.
$2,449,000
5Bedroom(s)
6Bathroom(s)
4,094Sqft

6252 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Now it’s your turn to live on the 18th hole of the Golden Bear Club golf course in a fully updated custom home, located on one of the most desirable streets in Keene’s Pointe. This house with a timeless design inside and out, has five bedrooms (two down and three up), four full bathrooms, three car garage, and incredible outdoor living with renovated pool and brand new pool enclosure.
$2,390,000
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
4,287Sqft

409 W 2nd Ave, Windermere, Florida 34786

Residential For Sale

UPSIDE REAL ESTATE INC
Under contract-accepting backup offers. Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and family.
$2,375,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,688Sqft

713 Main St, Windermere, Florida 34786

Residential For Sale

THE REAL ESTATE COLLECTION LLC
Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout.
$2,285,000
6Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
5,031Sqft
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