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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6134 Keenes Pointe Dr, Windermere, Florida 34786

Residential For Sale

WRA BUSINESS & REAL ESTATE
Welcome to a rare fully furnished opportunity in the heart of Keene’s Pointe, Windermere’s most acclaimed community. This renovated residence, with over 4,400 square feet of living space, has been reimagined to deliver not just a home, but an extraordinary lifestyle where every detail speaks of elegance, comfort, and sophistication.
$2,249,000
4Bedroom(s)
4Bathroom(s)
4,440Sqft

1238 Lake Whitney Dr, Windermere, Florida 34786

Residential For Sale

HOME WISE REALTY GROUP, INC.
BIG PRICE REDUCTION . MOTIVATED SELLER .Welcome to the exquisite and elegant GUARD GATED COMMUNITY OF Reserve At Belmere. A true luxury Tuscan style luxury home with spectacular views of Lake Whitney . Step into the grand entryway and you will be delighted with the enormous iron chandelier and breathtaking water views that will make you instantly fall in love.
$2,200,000
4Bedroom(s)
6Bathroom(s)
5,266Sqft

1020 Oakdale St, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
Under contract-accepting backup offers. Under Construction. Extraordinary new construction estate by renowned builder Davila Homes, nestled in the heart of Downtown Windermere. Meticulously designed and artfully executed, this five-bedroom, four-and-a-half-bathroom residence offers 3,994 square feet of luxurious living space.
$2,200,000
5Bedroom(s)
5Bathroom(s)
3,994Sqft

436 E 7th Ave, Windermere, Florida 34786

Residential For Sale

TALENT REALTY SOLUTIONS
Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center.
$2,175,000
4Bedroom(s)
5Bathroom(s)
3,136Sqft

647 Ridgewood Dr, Windermere, Florida 34786

Residential For Sale

PREMIER SOTHEBYS INT'L REALTY
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.
$2,150,000
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,681Sqft

6036 Greatwater Dr, Windermere, Florida 34786

Residential For Sale

KEENE'S POINTE REALTY
Welcome to Keene’s Pointe! Discover the charm of this custom-built home located on the 17th Fairway of the renown Jack Nicklaus Signature Golf Course and across from the lakefront mansions that line this quiet cul-de- sac on Greatwater Drive. This 4BR/4Full Bath/1 Half Bath golf course estate home exudes warmth from the gorgeous hardwood floors and abundant natural light.
$2,145,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,013Sqft

6564 Lagoon St, Windermere, Florida 34786

Residential For Sale

NOVA REAL ESTATE SERVICES INC
Under contract-accepting backup offers. Listed BELOW appraised value & PRICED TO SELL! With this brand new construction home, your dream lakefront lifestyle starts here!! Set along the tranquil waters of Lake Sawyer, this brand-new Davila Homes masterpiece blends refined luxury with the magic of everyday lake life. With 5 bedrooms, 4.5 baths, and 3,685 sq. ft.
$2,000,000
5Bedroom(s)
5Bathroom(s)
3,685Sqft

12235 Montalcino Circle, Windermere, Florida 34786

Residential For Sale

SOUTHERN REALTY GROUP LLC
Casa del Lago gated community in Windermere, Florida. Exquisite 4 bedroom/4.5 bath luxury residence showcasing exceptional craftsmanship and high-end finishes throughout. As you arrive you are welcomed by a circular driveway and quaint courtyard entrance. The first floor boasts a formal dining room,and a spacious gathering room anchored by a stunning stone two-sided fireplace.
$1,999,000
4Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
4,550Sqft

13048 Lake Roper Ct., Windermere, Florida 34786

Residential For Sale

WOODSTONE INVESTMENTS LLC
Back on the market, financing fell through. Priced to sell fast. Unmatched Value! The only Windermere lakefront home with boat access available under $2M. Don't miss this opportunity. Enjoy the e evenings to a breathtaking sunset at your own private lake in this stunning custom-built home. Land: 1.6 acres including lake portion with 135 feet direct lake frontage.
$1,999,000
5Bedroom(s)
4Bathroom(s)
4,130Sqft

84 Oakdale St, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Welcome to 84 Oakdale Street, an exceptional luxury residence in the heart of Windermere, Florida, crafted by the renowned Element Home Builders—a rare opportunity to own one of their highly sought-after homes.
$1,995,000
4Bedroom(s)
6Bathroom(s)
3,519Sqft

13137 Lake Butler Blvd, Windermere, Florida 34786

Residential For Sale

KELLER WILLIAMS REALTY SMART
Welcome to your very own slice of Windermere paradise—where luxury meets laid-back country living and yes, HORSES are welcome! Nestled on over an ACRE with NO HOA or DEED RESTRICTIONS, this stunning 3-bedroom, 3.5-bath home is perfect for anyone craving space, style, and a little bit of saddle time.
$1,989,999
3Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
3,240Sqft

6047 Blakeford Dr, Windermere, Florida 34786

Residential For Sale

CORCORAN PREMIER REALTY
Stunning Golf-Front Luxury in Keene’s Pointe! Welcome to 6047 Blakeford Drive—an impeccably remodeled 4-bedroom, 4-bath residence offering 4,156 sq. ft. of A/C living space and 6,230 sq. ft. under roof. Perfectly situated along the renowned Jack Nicklaus Signature Golf Course, this home blends timeless elegance with modern comfort in one of Windermere’s most sought-after communities.
$1,969,000
4Bedroom(s)
4Bathroom(s)
4,156Sqft
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