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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101 Lee St, Windermere, Florida 34786

Residential For Sale

ISLEWORTH REALTY LLC
A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding trees, this home combines comfort, style, and plenty of space for family and friends.
$1,550,000
5Bedroom(s)
4Bathroom(s)
4,186Sqft

11019 Kentmere Ct, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Under contract-accepting backup offers. Meticulously upgraded and thoughtfully designed, this expansive Mediterranean estate rests gracefully on a .34-acre cul-de-sac lot in the prestigious guard-gated community of Lake Butler Sound.
$1,500,000
4Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
3,813Sqft

17538 Black Rail St, Windermere, Florida 34786

Residential For Sale

GARCIA REALTY GROUP
Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage.
$1,500,000
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,522Sqft

11637 Brickyard Pond Ln, Windermere, Florida 34786

Residential For Sale

RE/MAX 200 REALTY
Under contract-accepting backup offers. Introducing a rare opportunity to own a truly remarkable lakefront estate in the heart of Windermere's prestigious Lake Burden South community.
$1,499,998
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,120Sqft

8375 Bowden Way, Windermere, Florida 34786

Residential For Sale

B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE
This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated.
$1,490,000
4Bedroom(s)
4Bathroom(s)
3,809Sqft

9649 Weatherstone Ct, Windermere, Florida 34786

Residential For Sale

SUMMERHILL REALTY GROUP LLC
Under contract-accepting backup offers. Welcome to Weatherstone on Lake Olivia, one of Windermere’s most sought-after gated communities. With only 13 custom executive homes, each set on expansive one-acre homesites, this neighborhood offers a rare blend of exclusivity, privacy, and charm.
$1,490,000
5Bedroom(s)
6Bathroom(s)
4,226Sqft

6443 Cartmel Lane, Windermere, Florida 34786

Residential For Sale

STOCKWORTH REALTY GROUP
Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted Reserve at Lake Butler Sound community, this meticulously crafted residence epitomizes luxury living. Boasting classical architecture and spanning 4,257 square feet, this property offers a sophisticated retreat with unparalleled amenities.
$1,475,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,257Sqft

7135 Horizon Cir, Windermere, Florida 34786

Residential For Sale

THE BOSCH GROUP
TODAY IS THE DAY! This beauty is back on the market due to no fault of the property and currently reduced $96,000! Nestled in the TRUE TOWN of WINDERMERE is this Absolutely stunning, meticulously maintained pool home with TALL CEILINGS and lots of land surrounding on both sides! This HIDDEN GEM has majestic mature oaks on a private .
$1,449,000
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,359Sqft

8304 Lookout Pointe Drive, Windermere, Florida 34786

Residential For Sale

GARCIA REALTY GROUP
Beauiful Home with Private Swimming Pool and summer kitchen at community of Windemere Trails, this rare 6BR/4.5BA, 4,500+sqft residence offers a feast for the senses with gorgeous Spanish architecture, a classic tile roof, lush tropical landscaping, and stunning exterior stonework.
$1,400,000
6Bedroom(s)
5Bathroom(s)
4,161Sqft

6533 Cartmel Ln, Windermere, Florida 34786

Residential For Sale

MAXIM REALTY ORLANDO
Tucked away in the prestigious guard-gated community of The Reserve at Lake Butler Sound, this exceptional 4-bedroom, 3.5-bath single-story pool home blends timeless Mediterranean style with modern sophistication. Set on over half an acre in a quiet cul-de-sac, the home welcomes you with a paver driveway, lush mature landscaping, and an elegant entry framed by architectural columns.
$1,398,888
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,751Sqft

11524 Claymont Cir, Windermere, Florida 34786

Residential For Sale

ALIGN REAL ESTATE LLC
Completely updated in recent years, this 5-bedroom, 4-bathroom home offers 3,358 SqFt of luxury living in Keene’s Pointe, Windermere’s premier 24-hour guard-gated community and home of the Golden Bear Club. From the start, the oversized driveway, accommodating up to nine vehicles, and three-car garage set this home apart.
$1,389,000
5Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,358Sqft

11333 Camden Park Dr, Windermere, Florida 34786

Residential For Sale

KARDOSH REALTY
One or more photo(s) has been virtually staged. Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.
$1,367,000
5Bedroom(s)
5Bathroom(s)
3,449Sqft
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