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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7545 Lake Albert Dr, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestled on an expansive lot in one of Windermere's most sought after communities, this stunning estate offers the perfect balance of privacy, comfort, and resort-style living just minutes from Walt Disney World and the best of Central Florida.
$1,100,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
3,425Sqft

7019 Windy Palm Way, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Sample Image The Baldwin is a beautifully designed two-story home offering 4 bedrooms, 3.5 baths, and over 3,400 square feet of living space. The open-concept main level features a spacious great room and dining area that flow seamlessly into the kitchen—perfect for family gatherings or entertaining.
$1,099,198
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,404Sqft

14371 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted Arlington Bonus new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting.
$1,086,436
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
3,100Sqft

8764 Lookout Pointe Dr, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Under contract-accepting backup offers. Experience all the MAGIC that living in Windermere has to offer with DISNEY FIREWORK VIEWS from your private pool deck every night! Waterviews, Florida Pines, blue skies, and palm trees right in your own backyard.
$1,085,000
4Bedroom(s)
4Bathroom(s)
3,423Sqft

14395 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
The Baldwin floor plan is a thoughtfully designed two-story home featuring 4 spacious bedrooms and 3.5 bathrooms, offering over 3,400 square feet of living space. The first floor boasts an inviting open-concept design, with a large great room adjacent to a dining room, perfect for gatherings and entertaining.
$1,084,558
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,404Sqft

2107 Westover Reserve Blvd, Windermere, Florida 34786

Residential For Sale

REAL BROKER, LLC
Discover this beautifully updated 4-bedroom, 4-bathroom home tucked inside the exclusive gated community of Westover Reserve in Windermere, renowned for its tree-lined streets and serene setting. This home seamlessly blends spacious living with exceptional craftsmanship and thoughtful design throughout.
$1,080,000
4Bedroom(s)
4Bathroom(s)
4,676Sqft

14347 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting.
$1,079,004
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
3,100Sqft

14365 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Under Construction. Sample Images The Ellington II – Designed for the Way You Live The Ellington II floor plan offers a spacious and modern two-story design, perfect for families and those who love to entertain.
$1,050,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,628Sqft

14427 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. Step into your next home at the Sweetwater in Palms at Windermere. With over 4,400 square feet, this expansive two-story floorplan offers six bedrooms and four and a half baths, blending luxury and function for today’s modern living. On the first floor, the owner’s suite is a private retreat with dual walk-in closets and a spa-inspired bath.
$1,049,657
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,443Sqft

7007 Windy Palm Way, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. The Ellington II offers the perfect balance of space, comfort, and style. This modern two-story home features 5 bedrooms, 3 baths, and over 3,500 square feet of living space designed for today’s lifestyle. The open-concept main level includes a spacious kitchen, dining area, and great room ideal for entertaining.
$1,048,337
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,628Sqft

11162 Ledgement Ln, Windermere, Florida 34786

Residential For Sale

INFINITY REALTY GROUP LLC
NEW TILE ROOF INSTALLED BEFORE CLOSING! Welcome to Glenmuir—one of Windermere’s most sought-after gated communities. This 4 bedroom, 3 full bath, plus 2 half bath home includes a dedicated office and an upstairs bonus room within a primarily single-story layout—a thoughtful blend of functionality and comfort.
$1,045,000
4Bedroom(s)
4Bathroom(s)
3,248Sqft

2128 Lake Crescent Court, Windermere, Florida 34786

Residential For Sale

M2M REALTY
LOCATION, LOCATION, LOCATION...One of the most spectacular lots located in the desirable community of Butler Bay! Double cul-de-sac lot dead ends and a three car side entry garage. Great, versatile floorplan that has a lot of different configurations! Formal dining and double-sided fireplace into the kitchen and the living room.
$1,010,000
4Bedroom(s)
3Bathroom(s)
2,987Sqft
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