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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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 rare Mediterranean-style estate on 3.5 private acres in Windermere—HOA FREE! This stunning 5-bedroom, 4-bath home features a custom heated pool, three-level design (and a Florida value with a “basement-like” floor), and parking for 6+ vehicles plus a 2-car carport.
$3,325,000
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
6,834Sqft

4711 Joanna Garden Ct, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Under contract-accepting backup offers. 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

13448 Bellaria Cir, Windermere, Florida 34786

Residential For Sale

KENNEDY REALTY GROUP LLC
Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria.
$3,200,000
6Bedroom(s)
7Bathroom(s)
DrivewayParking(s)
6,308Sqft

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

13125 Casabella Dr, Windermere, Florida 34786

Residential For Sale

ON ME REALTY
HUGE PRICE IMPROVEMENT – SELLER MOTIVATED 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.
$3,185,000
5Bedroom(s)
6Bathroom(s)
7,561Sqft

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

8222 Stone Mason Ct, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Welcome to 8222 Stone Mason Court—an exceptional J. Richard Watson estate perfectly positioned along the 8th green of the Jack Nicklaus Signature Course in the guard-gated community of Keene’s Pointe. Freshly finished throughout with upgraded lighting and timeless appointments, this 6,800+ sq. ft.
$2,895,000
6Bedroom(s)
7Bathroom(s)
Garage Faces RearParking(s)
6,834Sqft

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)
DrivewayParking(s)
8,372Sqft

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.
$2,795,000
5Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,105Sqft

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)
DrivewayParking(s)
6,996Sqft
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