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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12663 Hawkstone Dr, Windermere, Florida 34786

Residential For Sale

KELLER WILLIAMS CLASSIC
Discover the only single-story lakefront home available under $2 million on the prestigious Lake Sawyer. This rare opportunity offers unmatched privacy, breathtaking views, and true single-level luxury in one of Windermere’s most desirable neighborhoods. With 5 bedrooms, 3.5 bathrooms, an office, and a 3-car garage, this home blends comfort and sophistication.
$1,700,000
5Bedroom(s)
4Bathroom(s)
4,000Sqft

11015 Hawkshead Ct, Windermere, Florida 34786

Residential For Sale

CENTURY 21 CARIOTI
Dream home in Windermere! Nestled inside the gates of the luxurious community of Reserve at Lake Sound. Move-in ready home! Tile roof replaced in 2021. Heated area of 3868 sqft built with high quality material and finishing, tall ceilings and travertine floors in the common areas. The refurbishment, done 4 years ago, resulted in adding modern sophistication to the home.
$1,700,000
5Bedroom(s)
5Bathroom(s)
Garage Faces SideParking(s)
3,868Sqft

6220 Cartmel Ln, Windermere, Florida 34786

Residential For Sale

SOUTHERN REALTY GROUP LLC
Exquisite renovated home in the 24-hour guard gated community of Reserve at Lake Butler Sound. This beautiful Windermere home has been remodeled from the imported porcelain tile and hand scraped hard wood flooring, to the fully renovated kitchen, A/C with UV purification, and energy efficient double pane windows. Exterior upgrades include a shallow well for irrigation and resurfaced pool.
$1,699,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,347Sqft

7417 Lake Albert Dr, Windermere, Florida 34786

Residential For Sale

TEAM DONOVAN
Welcome to your private paradise at 7417 Lake Albert Drive, where stunning sunrises and serene waterfront living await you. Owners have the option to build a dock and enjoy some water sports on this beautiful lake. This exceptional 6-bed, 6.5-bath residence, nestled in the highly sought-after Lake Burden community, offers an unparalleled lifestyle.
$1,690,000
6Bedroom(s)
7Bathroom(s)
5,006Sqft

6161 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

THOMAS LYNNE REALTY GROUP LLC
One or more photo(s) has been virtually staged. LIVE IN KEENE'S POINTE FOR UNDER $300 A SQ FT!!! PRICE REDUCED $100K!!! $50K SELLER CREDIT!!! Currently the LOWEST PRICE per sq ft in Keene’s Pointe for sale this home screams VALUE!!! This 5BR/4.
$1,690,000
5Bedroom(s)
5Bathroom(s)
Garage Faces SideParking(s)
5,704Sqft

1703 Roberts Landing Rd, Windermere, Florida 34786

Residential For Sale

INTERNATIONAL NETWORK REALTY
This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living.
$1,680,000
4Bedroom(s)
5Bathroom(s)
3,288Sqft

311 E 8th Ave, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER RESIDENTIAL RE
Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere.
$1,660,000
5Bedroom(s)
4Bathroom(s)
CoveredParking(s)
3,805Sqft

13124 Filly Ct, Windermere, Florida 34786

Residential For Sale

HOME N OFFICES INTERNATIONAL
Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.
$1,649,000
5Bedroom(s)
3Bathroom(s)
3,300Sqft

11342 S Camden Commons Dr, Windermere, Florida 34786

Residential For Sale

NOBSKA REAL ESTATE LLC
SELLER MOTIVATED. SOLD PARTIALLY FURNISHED. Situated at highly coveted community of Keenes Point in Windermere, this exquisitely home refined luxury living. FULLY REMODELED, Featuring six expansive bedrooms and five impeccably full bathrooms, and two half baths, every detail of this residence has been thoughtfully elevated.
$1,639,985
6Bedroom(s)
7Bathroom(s)
3,625Sqft

11923 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

JULIAN PROPERTIES, INC.
Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace.
$1,630,000
3Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
2,238Sqft

11056 Clipper Ct, Windermere, Florida 34786

Residential For Sale

VINTAGE REALTY GROUP LLC
Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina for your boat that is directly connected to Lake Down and the Butler Chain of Lakes * Oversized 4 Car Garage with Drive Through Doors on Front & Rear of the 3rd Bay * Over 1
$1,600,000
5Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
6,375Sqft

2509 Ridgewind Way, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
If you’ve dreamed of a home that feels both timeless and tailor-made for modern living, welcome to 2509 Ridgewind Way in the gated Estates at Windermere. Set on .75 acre this updated Southern estate combines architectural charm and every day comfort. A wrap-around front porch framed by copper lanterns and stately oaks sets the tone for the relaxed elegance inside.
$1,585,000
4Bedroom(s)
4Bathroom(s)
Garage Faces SideParking(s)
3,844Sqft
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