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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7681 Fordson Ln, Windermere, Florida 34786

Residential Lease For Rent

REILE REALTY CORP
Experience modern, energy-efficient living with SOLAR PANELS that provide sustainable power and an exceptionally low electric bill! This beautiful townhome for rent is located in the highly desirable community of Windermere Sound. Offering 4 bedrooms and 2.5 bathrooms, this spacious property features ceramic tile flooring in the main areas and carpet in the bedrooms for added comfort.
$2,900
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,997Sqft

7505 Fairgrove Ave, Windermere, Florida 34786

Residential Lease For Rent

METROPOLITAN R.E SOLUTIONS INC
Beautiful two-story home in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,980 sq. ft. of elegant living space. The primary suite is located upstairs, while bedrooms 2 and 3 share a convenient Jack & Jill bathroom.
$2,900
3Bedroom(s)
3Bathroom(s)
1,980Sqft

5333 Keenes Pheasant Drive, Windermere, Florida 34786

Residential Lease For Rent

LIFESTYLE INTERNATIONAL REALTY
Welcome Home to this gorgeous MOVE IN ready Summerport Townhome! This home is conveniently located right in front of Keene's Elementary school, directly to your left is a plaza with a nail salon, Foxtail Coffee and Kelly's Ice Cream and more. A park is within 5 minutes walking distance from the house, making outings in the evening enjoyable with everything the community has to offer.
$2,900
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,461Sqft

13833 Bridgewater Crossings Blvd, Windermere, Florida 34786

Residential Lease For Rent

BAHIA INTERNATIONAL REALTY
Beautiful 4BED/3.5BATH home in the community of Summer port, Windermere. This energy efficient home comes with 2 master suites, one of them is located on the first floor.
$2,899
4Bedroom(s)
4Bathroom(s)
2,451Sqft

13645 Riggs Way, Windermere, Florida 34786

Residential Lease For Rent

CINO INTERNATIONAL INC
Beautiful 3 bedroom one story beautiful home. This split plan home has a spacious great room which connects to the gourmet kitchen featuring beautiful granite countertops, a pantry with custom wood shelves, a breakfast bar and dinette area and provides the perfect space to spend time with family and friends.
$2,875
3Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
2,023Sqft

7819 Hardenton St, Windermere, Florida 34786

Residential Lease For Rent

COLDWELL BANKER REALTY
Welcome to a townhome that surprises at every turn—fully remodeled with modern elegance and thoughtful upgrades throughout. Located in the heart of the highly desirable Wickham Park community, this charming residence offers serene views right from your front door. Here are some of the features and upgrades you can spot on. Brand New Appliances: Washer, dryer, range, and microwave—all included.
$2,850
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,500Sqft

13744 Summer Harbor Ct., Windermere, Florida 34786

Residential Lease For Rent

FLORIDA REALTY INVESTMENTS
*** CHARMING WATERFRONT *** 2-STORY SINGLE FAMILY FOR RENT, LOCATED IN SUMMERPORT COMMUNITY IN WINDERMERE. BUILT IN 2016, this beautiful home has 3 spacious bedrooms, 2.5 bathrooms with 2205 SQFT of living space.
$2,850
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,205Sqft

13892 Summerport Trail Loop, Windermere, Florida 34786

Residential Lease For Rent

MAY HO REALTY
... Move in ready... ... LAWN CARE, WASHER, and DRYER are included... ... This beautiful formal model home in Summerport and offers 4 bedroom/2.5 bath/2 car rear garage is loaded with a lot of upgrades... ... All bedrooms are located on the 2nd floor... ... Walking distance to Publix supermarket, Windermere High School, and local shopping... ...
$2,850
4Bedroom(s)
3Bathroom(s)
2,024Sqft

13718 Beckman Dr, Windermere, Florida 34786

Residential Lease For Rent

MD3 HOMES LLC
Beautiful TOWHOME AT WINDERMERE AREA. kitchen with upgraded 42`` cabinets, stainless steel appliances. Upstairs vinyl floor, Master suite with walk in closet ,bathroom with dual sinks. Club house with pool.
$2,800
3Bedroom(s)
3Bathroom(s)
1,912Sqft

8620 Wellington Blue Lane, Windermere, Florida 34786

Residential Lease For Rent

SOUTHERN REALTY GROUP LLC
Beautiful townhome in Windermere Trails with first floor master bedroom. Excellent location - walking distance to Bay Lake Elementary, as well as shopping and dining. This well maintained unit offers 3 bedrooms (master down with 2 closets) and two bedrooms with full bath, bonus/loft area and laundry located on the second floor. Tastefully decorated throughout with gray and white accents.
$2,800
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,822Sqft

11649 Black Rail St, Windermere, Florida 34786

Residential Lease For Rent

ALTIS REALTY
Spacious 3-bedroom, 2.5-bath townhome located in the heart of Windermere with 2,139 sq. ft. of open living space. The gourmet kitchen features a large island, perfect for entertaining, while the upstairs includes a convenient laundry room. Enjoy a private fenced backyard with a cozy patio, plus a 2-car covered garage in the rear.
$2,800
3Bedroom(s)
3Bathroom(s)
2,139Sqft

8620 Wellington Blue Ln, Windermere, Florida 34786

Residential Lease For Rent

SOUTHERN REALTY GROUP LLC
Beautiful townhome in Windermere Trails with first floor master bedroom. Excellent location - walking distance to Bay Lake Elementary, as well as shopping and dining. This well maintained unit offers 3 bedrooms (master down with 2 closets) and two bedrooms with full bath, bonus/loft area and laundry located on the second floor. Tastefully decorated throughout with gray and white accents.
$2,800
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,768Sqft
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