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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6564 Lagoon St, Windermere, Florida 34786

Residential For Sale

NOVA REAL ESTATE SERVICES INC
Listed BELOW appraised value & PRICED TO SELL! With this brand new construction home, your dream lakefront lifestyle starts here!! Set along the tranquil waters of Lake Sawyer, this brand-new Davila Homes masterpiece blends refined luxury with the magic of everyday lake life. With 5 bedrooms, 4.5 baths, and 3,685 sq. ft. of beautifully designed living space, every element is crafted to impress.
$2,000,000
5Bedroom(s)
5Bathroom(s)
3,685Sqft

5412 Water Creek Dr, Windermere, Florida 34786

Residential For Sale

THE REAL ESTATE COLLECTION LLC
Adjacent to the northwest corner of Lake Butler, beautifully set along the shores of Lake William Davis, this custom Mediterranean-inspired estate captures the essence of timeless design and relaxed Florida living. Framed by lush landscaping and serene water views, the home blends classic architectural details with fresh, inviting interiors.
$1,999,900
4Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,247Sqft

13048 Lake Roper Ct., Windermere, Florida 34786

Residential For Sale

WOODSTONE INVESTMENTS LLC
Priced to sell fast. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage.
$1,999,000
5Bedroom(s)
4Bathroom(s)
4,130Sqft

13137 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

KELLER WILLIAMS REALTY SMART
Welcome to your very own slice of Windermere paradise—where luxury meets laid-back country living and yes, HORSES are welcome! Nestled on over an ACRE with NO HOA or DEED RESTRICTIONS, this stunning 3-bedroom, 3.5-bath home is perfect for anyone craving space, style, and a little bit of saddle time.
$1,989,999
3Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,240Sqft

6047 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Stunning Golf-Front Luxury in Keene’s Pointe! Welcome to 6047 Blakeford Drive—an impeccably remodeled 4-bedroom, 4-bath residence offering 4,156 sq. ft. of A/C living space and 6,230 sq. ft. under roof. Perfectly situated along the renowned Jack Nicklaus Signature Golf Course, this home blends timeless elegance with modern comfort in one of Windermere’s most sought-after communities.
$1,979,000
4Bedroom(s)
4Bathroom(s)
4,156Sqft

13036 Lake Roper Ct, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Prepare to be dazzled by this exquisitely remodeled waterfront estate in a gated Windermere community. On over a one-acre private lot, the home sits on the shores of the pristine 38-acre Lake Roper. Massive double doors greet you as you enter into impeccable craftsmanship and high-end finishes that sparkle amongst the lakefront backdrop.
$1,950,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
4,044Sqft

13420 Bonica Way, Windermere, Florida 34786

Residential For Sale

FERRELL REALTY, INC.
Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new AC system in August 2025.
$1,950,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
4,489Sqft

9070 Ron Den Ln, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
VERY ATTRACTIVE TERMS SELLER FINANCING NOW AVAILABLE FOR THIS REMARKABLE BUTLER CHAIN OF LAKES HOME, CONTACT AGENT FOR MORE INFO!!! Discover the perfect blend of luxury, comfort, and outdoor living on the highly sought-after Lake Down of the Windermere Chain of Lakes.
$1,890,000
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,384Sqft

9922 Brentford Ct, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
If you want something turn-key in Keene’s Pointe, sitting in one of the most desirable locations in the community, then look no further. This is a home you can move into today, sit down and live, without touching a single thing. This home has not only been renovated from end to end, but also has a three year old new tile roof!! Every square inch of the house feels brand new as you walk thru.
$1,890,000
6Bedroom(s)
4Bathroom(s)
3,894Sqft

11312 Shandon Park Way, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Welcome to this stunning seven-bedroom, five-bath residence in the exclusive guard-gated community of Reserve at Belmere. This beautifully remodeled home offers 4,902 square feet of living space and a functional two-story layout featuring a spacious family room, formal living and dining areas, and a large kitchen with granite countertops, modern cabinetry and stainless steel appliances.
$1,790,000
7Bedroom(s)
5Bathroom(s)
4,914Sqft

12001 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

JULIAN PROPERTIES, INC.
Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere.
$1,775,000
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
3,135Sqft

3130 Butler Bay Dr N, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER REALTY
This one-of-a-kind estate in the gated Windermere Club combines timeless elegance with rare features seldom found in the area, including four garage bays—one of them separate from the rest, with an adjoining flex space that can serve as a gym, studio, or easily transform into private guest quarters or multigenerational living.
$1,725,000
4Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
4,490Sqft
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