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.

Sort Option
  • Listing ID
  • Built up Area
  • Price
  • Pictures
  • Add date
  • Featured
Grid
List
Map

12023 Gold Creek Trl, Windermere, Florida 34786

Residential For Sale

KAZA REAL ESTATE LLC
Welcome to this beautiful single-family residence, located on a premium corner lot spanning over 9,000 square feet in the prestigious and highly sought-after community in Windermere. This exceptional home combines comfort, and functionality, offering an unmatched lifestyle in one of Central Florida’s most desirable neighborhoods, the Windermere Trails.
$1,200,000
7Bedroom(s)
4Bathroom(s)
3,928Sqft

1361 Whitney Isles Dr, Windermere, Florida 34786

Residential For Sale

ALVES AND HOWELL REALTY
Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping.
$1,200,000
4Bedroom(s)
4Bathroom(s)
2,787Sqft

11325 Fenimore Ct, Windermere, Florida 34786

Residential For Sale

COMPASS FLORIDA LLC
One or more photo(s) has been virtually staged. Newly added virtually staged images to help with your interior design inspiration! Come home to a golf enthusiast’s dream set along the 6th Hole of the renowned Jack Nicklaus Signature 18-Hole golf course, The Golden Bear Club (est. 1999).
$1,200,000
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,658Sqft

3629 Lake Buynak Rd, Windermere, Florida 34786

Residential For Sale

KELLER WILLIAMS ELITE PARTNERS III REALTY
BACK ON THE MARKET DUE TO NO FAULT OF THE PROPERTY OR SELLERS, BUT DUE TO BUYER UNFORSEEN CANCELLATION. Welcome to 3629 Lake Buynak Drive—an exceptional opportunity for investors, a custom home build or buyers seeking multigenerational living with flexibility and future upside. Situated in a desired area and on an oversized 1.
$1,200,000
4Bedroom(s)
4Bathroom(s)
2,618Sqft

3443 Wild Myrtle Ct, Windermere, Florida 34786

Residential For Sale

JULIAN PROPERTIES, INC.
Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a serene 1.2-acre cul-de-sac lot in the esteemed Lake Butler Estates of Windermere, Florida. This expansive 5-bedroom, 3-bathroom residence offers 2,918 square feet of thoughtfully designed living space, combining modern updates with timeless charm.
$1,200,000
5Bedroom(s)
3Bathroom(s)
Garage Faces SideParking(s)
2,918Sqft

11334 Camden Loop Way, Windermere, Florida 34786

Residential For Sale

COLDWELL BANKER REALTY
Absolutely turn-key home in the much desired area of Camden in the country club Windermere community of Keene’s Pointe. This 4 bedroom, 3 bath home with a pool and three car garage is ready to move in today. All on one floor, this floorpan is incredibly popular due to its easy accessibility and fantastic flow.
$1,190,000
4Bedroom(s)
3Bathroom(s)
3,021Sqft

14250 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.
$1,174,935
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
3,100Sqft

9353 Gotha Rd, Windermere, Florida 34786

Residential For Sale

REAL LIVING R E SOLUTIONS
Rare Opportunity…1+ Acre…Courtyard Design… Fully Updated Pool Home. This distinctive U-shaped pool home features a 2000 sq/ft enclosed Atrium for exceptional outdoor living. Inside, every space is very large with Sliding Glass Doors creating a wall of glass for you to overlook the star of the show which is your sparkling 18x36 inground pool, private courtyard and a new outdoor kitchen.
$1,174,900
4Bedroom(s)
4Bathroom(s)
OversizedParking(s)
3,042Sqft

1927 Watermere Ln, Windermere, Florida 34786

Residential For Sale

YOUR HOME SOLD GUARANTEED REALTY
Under contract-accepting backup offers. Luxury living in one of Central Florida's most sought-after neighborhoods, Windermere Grande. These 5 bedrooms, 3.5 baths single-family home offers .85 acres of land and a sprawling 3,053 square feet of living space. This gated neighborhood provides direct access to an array of outdoor amenities including playgrounds, walking paths, and nearby lake views.
$1,146,000
4Bedroom(s)
4Bathroom(s)
3,053Sqft

14225 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.
$1,139,000
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
4,443Sqft

14201 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 Welcome to the Arlington with Bonus! This stunning 3,099 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends.
$1,125,970
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,100Sqft

14261 Crest Palm Ave, Windermere, Florida 34786

Residential For Sale

OLYMPUS EXECUTIVE REALTY INC
One or more photo(s) has been virtually staged. The Ellington II floor plan offers a modern, spacious two-story layout ideal for families and entertaining. It includes 4-5 bedrooms, 3 bathrooms, and expansive living areas. The main level features an open concept kitchen, dining, and great room, perfect for socializing. A private owner’s suite and an optional guest suite offer versatility.
$1,119,435
6Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,628Sqft
432 Results returned.Per Page