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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7211 Still Pond Ln, Windermere, Florida 34786

Residential Lease For Rent

MBT REALTY LLC
This property will be ready to be your home next January.Welcome to this former model home in one of Windermere's coveted communities. This custom-designed model is situated on a premium corner lot and offers a combination of luxury, convenience and comfort. As you drive down beautifully manicured streets and past serene lakes, you will arrive at this charming home with its quaint covered porch.
$4,490
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,091Sqft

11445 Vicolo Loop, Windermere, Florida 34786

Residential Lease For Rent

BLUE MAGNOLIA REALTY LLC
Gorgeous pool home ready for tenant in desirable gated Belmere community with private pool and spa. Solid flooring throughout. Primary bedroom and additional bedrooms on first floor. Bonus room/bedroom and bath on second floor. 3 car garage; tile roof; paver driveway. Community has tennis, playground amenities and very walkable. Pool and lawncare included in rent.
$4,400
4Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
3,144Sqft

5426 Gemgold Ct, Windermere, Florida 34786

Residential Lease For Rent

LPT REALTY, LLC
Discover the best current value for a lakefront property in Windermere with this stunning WATERFRONT HOUSE featuring a private DOCK in the highly sought-after Summerport community! Recently remodeled on the first floor, this home now features a captivating open layout complemented by newer luxury vinyl floors throughout.
$4,400
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,648Sqft

11646 Hampstead St, Windermere, Florida 34786

Residential Lease For Rent

MILA REALTY
Available NOW! $0 application fee for pre-approved applicants. Welcome to Enclave at Windermere Landing! Discover luxurious one-level living with soaring high ceilings that create an airy, grand atmosphere throughout. This exceptional pool home offers 3 bedrooms plus a versatile den/office (easily convertible to a 4th bedroom), 2.5 baths, and a spacious 3-car garage.
$4,395
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,798Sqft

2943 Marquesas Ct, Windermere, Florida 34786

Residential Lease For Rent

INTEGRITY REAL ESTATE GROUP, LLC
Come tour this incredible New England-style pool home in the Town of Windermere that sits on a meticulously manicured one-acre corner lot on a serene, tree-lined street, in the gated community of Lake Crescent Reserve. Lake Crescent is an exclusive community of 21 custom homes with mostly waterfront homes on Lake Crescent.
$4,200
4Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,145Sqft

12821 Westside Village Loop, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY KISSIMMEE
This stunning home sits on a corner 5 bedrooms plus an office and huge bonus room. once you into the large foyer where you will find the office with a double door entry and a guest bath. The formal dining room has a contemporary tray ceiling and leads into the butlers pantry with built in cabinetry and a large walk in pantry.
$4,150
5Bedroom(s)
4Bathroom(s)
3,689Sqft

12676 Salomon Cove Dr, Windermere, Florida 34786

Residential Lease For Rent

LPT REALTY, LLC
Welcome to this rare 6-bedroom, 4-bathroom single-family home offering over 3,600 sq. ft. of living space in the highly desirable community of Westside Village in Windermere. Nestled in a top-rated school district and just a 10-minute drive to Walt Disney World, this home combines comfort, convenience, and exceptional location.
$4,150
6Bedroom(s)
4Bathroom(s)
3,667Sqft

13607 Zori Ln, Windermere, Florida 34786

Residential Lease For Rent

BRAZA HOMES
Beautifully maintained 4-bedroom, 2-bath home for rent in the sought-after Providence Community within the top-rated Windermere school district. Features include 10-ft ceilings, plantation shutters, crown molding, granite countertops, stainless steel appliances, and a spacious open floor plan.
$3,650
4Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
2,516Sqft

8712 Crescendo Ave, Windermere, Florida 34786

Residential Lease For Rent

TOPSKY REALTY INC
Welcome to this 4/bed 3.5/bath home with fenced yard in the prestige Windermere Trails. The home features a spacious kitchen with Whirlpool SS appliances, 42" upper cabinets, large center island, walk in pantry, granite countertops open to the Family room and adjacent to your private den/study. Visitors will feel right at home in the main floor guest suite.
$3,500
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,911Sqft

13154 Kegan Street, Windermere, Florida 34786

Residential Lease For Rent

WEICHERT REALTORS HALLMARK PRO
The house has 4 Bed rooms and three and a half bath rooms, two of them are master bedrooms with walk in closets and master bathrooms with double vanity. There IS another very big bonus room with bath room and walking closet on top of the garage. Which can be used as an office . In this way this house has 5 bedrooms and 4.5 bathrooms. Open floor concept.
$3,500
5Bedroom(s)
5Bathroom(s)
2,961Sqft

7984 Brofield Avenue, Windermere, Florida 34786

Residential Lease For Rent

UNIONE REALTY INC
This beautiful water view home in Berkshire Park is a must see! Vaulted foyer entryway reveals the open feeling of this gorgeous 4 bedroom home. Lots of upgrades throughout, including: laminate flooring throughout the property except tile in wet areas, 42" maple cabinets and granite countertops in kitchen, and stainless steel appliances.
$3,500
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,794Sqft

10733 Village Lake Rd, Windermere, Florida 34786

Residential Lease For Rent

CENTURY 21 CARIOTI
Newly renovated 4 Bedroom 3 1/2 Bathroom Town Home with 2 Car Garage. Open Living Room/ Dinning Room / Kitchen combo with Tile floors. Gourmet Kitchen has Stainless Steal Appliances, Granite Counter Tops and upgrade Cabinets. Sliding Glass Doors that open up to the courtyard and attached 2 Car Garage. This Property offers 2 Master Bedrooms, one on the ground level and one on the second level.
$3,475
4Bedroom(s)
4Bathroom(s)
1,834Sqft
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