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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7351 Millstone St, Windermere, Florida 34786

Residential Lease For Rent

FRONTLINE FLORIDA REALTY, INC.
Beautiful Unfurnished 3/2 townhome in the best location in entire community! This upgraded, sparkling clean unit with stainless steal appliances, Fridge, Washer and Dryer located directly across from the park and the baseball diamond and is practically in Disney World's backyard! You'll love the spectacular nightly fireworks show from your master bedroom or front porch and fall in love with the ne
$2,500
3Bedroom(s)
2Bathroom(s)
On StreetParking(s)
1,510Sqft
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13348 Abuela Aly, Windermere, Florida 34786

Residential Lease For Rent

EPIC REALTY
NO SMOKING AND NO PETS ALLOWED. Welcome to this beautiful home located in the desirable community of Windermere! This well-maintained property is vacant and available for move-in. Offering modern finishes, spacious living areas, and an inviting atmosphere, it’s the perfect place to call home.
$2,500
3Bedroom(s)
3Bathroom(s)
1,503Sqft
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14284 Desert Haven St #806, Windermere, Florida 34786

Residential Lease For Rent

CINO INTERNATIONAL INC
VACANT! Great location! Great Home! Move in this Great home inside the lovely Oasis Cove community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has all tiled floor. It oversees the front porch. Kitchen has all fully appliances and granite counter top. You can also enjoy Disney firework at night.
$2,500
3Bedroom(s)
3Bathroom(s)
1,840Sqft
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8398 Iron Mountain Trl, Windermere, Florida 34786

Residential Lease For Rent

METROPOLITAN R.E SOLUTIONS INC
Beautiful townhouse with 3 bedrooms and 2.5 bathrooms located in the sought-after Windermere Trails community ready for a quick move-in! This home welcomes you with a bright and open layout, featuring a modern kitchen with granite countertops, stainless steel appliances, and a large breakfast bar that flows perfectly into the dining and living areas.
$2,500
3Bedroom(s)
3Bathroom(s)
1,540Sqft
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7334 Brightland St, Windermere, Florida 34786

Residential Lease For Rent

WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
3BR townhome in the desirable Lake Burden community. It starts with great curb appeal - nicely maintained landscaping courtesy of the HOA. Common living areas on ground floor and bedrooms upstairs. Being that this an end unit, the entry to your home is on the side of the house, and greeting you when you open the front door is a large family room with lots of natural sunlight.
$2,450
3Bedroom(s)
3Bathroom(s)
Garage Faces RearParking(s)
1,883Sqft
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8180 Boat Hook Loop #304, Windermere, Florida 34786

Residential Lease For Rent

RE/MAX PRIME PROPERTIES
The perfect blend of comfort, convenience, and Central Florida lifestyle! This beautiful ground-floor residence offers effortless living with an open-concept floor plan that flows seamlessly from the kitchen to the living and dining areas—perfect for relaxing or entertaining.
$2,450
3Bedroom(s)
2Bathroom(s)
NoneParking(s)
1,455Sqft
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7624 Sutherton Ln, Windermere, Florida 34786

Residential Lease For Rent

METROPOLITAN R.E SOLUTIONS INC
Townhome located in Wickham Park in Windermere. Granite Counters and solid wood cabinets. Large combined living room/dining room area. 3-bed, 2.5-bath. Featuring stainless appliances, a 2-car garage, a private courtyard, and access to community amenities including a pool and clubhouse.
$2,450
3Bedroom(s)
3Bathroom(s)
1,565Sqft
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12967 Calderdale Avenue, Windermere, Florida 34786

Residential Lease For Rent

JAMIESON PROPERTIES, INC.
Nicely appointed end unit townhouse located in Wickham Park. Great floor plan with Master and Laundry on the first floor with additional bedrooms and loft upstairs. Available for occupancy now. Home has tile throughout and carpet in the bedrooms, stainless steal appliances, very clean. Community pool and club house and convenient to shopping, restaurants, and area theme parks.
$2,400
3Bedroom(s)
3Bathroom(s)
CoveredParking(s)
1,751Sqft
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8265 Maritime Flag St #101, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA REALTY INVESTMENTS
Built in 2012, this spacious 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort, convenience, and community living. Step inside to find a bright and open floor plan featuring a large kitchen, dining area, and living room, perfect for entertaining or relaxing at home. All bedrooms are conveniently located on the second floor, providing added privacy.
$2,375
3Bedroom(s)
3Bathroom(s)
1,644Sqft
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5589 Remsen Cay Lane, Windermere, Florida 34786

Residential Lease For Rent

INVITATION HOMES
You're going to love this home! The spacious kitchen is exquisite with gorgeous cabinetry, contemporary counters, and stainless steel appliances. The open floor plan is full of natural light, making this home perfect for entertaining. The primary bath is stunning with designer touches, a separate shower, and a garden tub.
$2,340
4Bedroom(s)
3Bathroom(s)
2,600Sqft
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Windermere, Florida 34786

Residential Lease For Rent

ORLANDO REALTY & PROPERTY MGNT
Windermere 3 Bedrm 2 Car Garage Townhome Near Disney For Rent SEE TERMS Priced Low, Call Now! Very Clean Property, 2 Car Garage, Brick Pavered Backyard, Patio Granite Countertops, 42” Cabinets, Tile Flooring, Carpeted Bedrooms, Ceiling Fan In Many Rooms, COMMUNITY Pool! COMMUNITY Playground, JUST 35 MINUTES To Downtown Orlando, JUST 40 MINUTES To The Airport, JUST MINUTES To All Theme Parks,
$2,317
3Bedroom(s)
3Bathroom(s)
1,644Sqft
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8168 Boat Hook Loop #707, Windermere, Florida 34786

Residential Lease For Rent

TEAM DONOVAN
Welcome to this move in ready condo in the desirable Lakeside at Lakes of Windermere. This unscale condo community has everything. This first floor 3 bed 2 bath unit is located just across the street from the community clubhouse and pool. With close proximity to the Lakeside Village for shops, restaurants and grocery store, and only 15 mins to Disney.
$2,300
3Bedroom(s)
2Bathroom(s)
1,332Sqft
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