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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12132 Montalcino Cir, Windermere, Florida 34786

Residential For Sale

BELLA VIEW REALTY LLC
Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.
$3,950,000
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
5,709Sqft

9648 Mccormick Pl, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout.
$3,800,000
3Bedroom(s)
4Bathroom(s)
4,751Sqft

10545 Down Lakeview Cir, Windermere, Florida 34786

Residential For Sale

COLONIALTOWN REALTY
Enjoy stunning sunsets from your private estate with expansive views, located on Lake Down, the prestigious Butler Chain of Lakes in Windermere. This well-appointed property features 2.78 acres with fully fenced terraced grounds, electric security gates, brick pavers, mature landscaping for privacy, and 130 feet of water frontage with a seawall, enclosed boat house, dock, and lift.
$3,795,000
5Bedroom(s)
7Bathroom(s)
DrivewayParking(s)
7,263Sqft

12812 Jacob Grace Ct, Windermere, Florida 34786

Residential For Sale

EXP REALTY LLC
Experience Unmatched Lakeside Luxury in a Custom-Built Masterpiece Discover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community.
$3,775,000
4Bedroom(s)
5Bathroom(s)
6,054Sqft

2844 Marquesas Ct, Windermere, Florida 34786

Residential For Sale

DOUGLAS ELLIMAN
Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmering waters of Lake Crescent. Nestled within the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece offers just under 6,000 square feet of newly remodeled, reimagined luxury living.
$3,700,000
4Bedroom(s)
3Bathroom(s)
Garage Faces SideParking(s)
5,365Sqft

7706 Ficquette Rd, Windermere, Florida 34786

Residential For Sale

REVEL REALTY LLC
Under contract-accepting backup offers. NEW CONSTRUCTION Luxury Lakefront Estate | 6,202 Sq Ft a Private Guest House | 6 Beds + Office + Loft | Pool | No HOA | Boat Dock Experience unmatched lakeside living in this west-facing, 6,202 sq ft custom estate featuring 6 bedrooms with private en-suites, including a guest suite.
$3,700,000
6Bedroom(s)
7Bathroom(s)
Garage Door OpenerParking(s)
6,202Sqft

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)
DrivewayParking(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
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)
DrivewayParking(s)
8,203Sqft

6130 Grosvenor Shore Dr, Windermere, Florida 34786

Residential For Sale

DOUGLAS ELLIMAN
Remarkable Waterview Estate in Keene’s Pointe! Heated Saltwater Pool, Main-Floor Living, and Expansive Outdoor Living Space.
$3,500,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,676Sqft

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

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
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