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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9310 Isleworth Gardens Dr, Windermere, Florida 34786

Residential For Sale

UPSIDE REAL ESTATE INC
Experience the art of fine living in this exquisite one-story Modern Mediterranean garden villa, offered fully furnished with a curated designer furniture package. Every detail has been thoughtfully crafted, blending timeless architecture with refined finishes and effortless comfort. Inside, travertine floors, wood-beamed ceilings, and solid wood doors set a warm, sophisticated tone.
$3,700,000
3Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,333Sqft

4812 Alexandra Garden Ct, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home.
$3,699,000
3Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,262Sqft

5024 Sawyer Cove Way, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living.
$3,600,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
5,501Sqft

13643 Lake Cawood Dr, Windermere, Florida 34786

Residential For Sale

JWJ REALTY LLC
Under contract-accepting backup offers. Luxury HOME 8 Bedroom (all Suite) - with One acre lot in exclusive Lake Cawood Estates in Windermere. Built from ICF insulated concrete blocks for superior energy efficiency and hurricane protection with foam roof insulation, barrel tile roof and $25k whole house generator included.
$3,590,000
8Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
8,203Sqft

13125 Casabella Dr, Windermere, Florida 34786

Residential For Sale

ON ME REALTY
Welcome to Your Fully Automated Home in Casabella at Windermere Introducing a spectacular 7,561 sq. ft. estate home perfectly positioned on a half-acre lot with tranquil pond views at both the front and rear. This 5-bedroom, 5.5-bath masterpiece offers total privacy, elegance, and cutting-edge technology.
$3,590,000
5Bedroom(s)
6Bathroom(s)
7,561Sqft

10577 Down Lakeview Cir, Windermere, Florida 34786

Residential For Sale

THE SIMON SIMAAN GROUP
This exceptional lakefront home is located on The Butler Chain of Lakes with 137 feet of pristine shoreline and is situated on almost one dry acre. At first glance you will immediately fall in love with this beautiful custom home boasting amazing panoramic views and nightly Disney fireworks.
$3,500,000
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
5,273Sqft

13305 Bellaria Cir, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
In the gated Bellaria community, featuring six expansive bedrooms, including two primary suites and four en suites, this residence is an ideal blend of privacy and convenience with a beautiful lake view. Enjoy your private cinema, this Toll Brothers estate blends luxury and comfort with dramatic ceilings, an open floor plan, and travertine marble flooring on main areas.
$3,490,000
6Bedroom(s)
8Bathroom(s)
6,930Sqft

3426 Cocard Ct, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
An exceptional estate, masterfully renovated and transformed into a reimagined showplace: complete with a brand-new exquisite chef’s kitchen, family room, and bar with glass enclosed wine rack – plus mammoth private swimming pool and spa with new decking and checkerboard synthetic turf with multiple sitting venues.
$3,450,000
4Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
7,222Sqft

4077 Isabella Cir, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
One or more photo(s) has been virtually staged. Stunning contemporary estate on over 1 acre in guard-gated Casabella. This 6-bedroom, 6 full bath, 2 half bath custom home offers over 7,500 sq ft of luxurious living. Open-concept design with soaring ceilings, walls of glass, and high-end finishes throughout.
$3,450,000
6Bedroom(s)
8Bathroom(s)
7,559Sqft

9731 Chestnut Ridge Dr, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.
$3,400,000
4Bedroom(s)
4Bathroom(s)
Circular DrivewayParking(s)
4,877Sqft

2012 Bellamere Ct, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Exquisitely appointed and elegantly packaged former model home, showcasing the pinnacle of perfection, from luxury home builder Element Homes. This masterpiece stands supreme for its high-quality fit and finish and a highly desirable floorplan – featuring a great room combination of family room, dining room, and kitchen – masterfully crafted to exhibit transitional style and function.
$3,375,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
4,701Sqft

4301 Down Point Ln, Windermere, Florida 34786

Residential For Sale

MARK SPAIN REAL ESTATE
One or more photo(s) has been virtually staged. EXPERIENCE LUXURY LAKEFRONT LIVING in this one-of-a-kind MEDITERRANEAN-STYLE WATERFRONT HOME with a CUSTOM HEATED POOL—and HOA FREE! Nestled on 3.5 ACRES IN the heart of Windermere, this exceptional residence blends elegance, privacy, and functionality, offering 5 bedrooms, 4 bathrooms, and garage parking for up to 6 vehicles, plus a 2-car carport.
$3,350,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
6,834Sqft
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