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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14242 Desert Haven St #ge, Windermere, Florida 34786

Residential Lease For Rent

REAL BROKER, LLC
Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a comfortable, low-maintenance lifestyle just minutes from Disney—with clear views of the nightly fireworks from your own home. The interior features a functional two-story layout with all bedrooms located upstairs, providing separation between living and private spaces.
$2,550
3Bedroom(s)
3Bathroom(s)
1,534Sqft

7231 Shadeview Aly, Windermere, Florida 34786

Residential Lease For Rent

SUNNY 365 REALTY GROUP
Beautiful 3 beds, 2.5 baths, 2 car garage townhome at Ashlin Park in the heart of Windermere. Must see all this community has to: Community Pool, Club House, Playground, Conservation areas, ponds, access to bike trail and just at walking distance from Restaurants and market places. Right next to the 535 road, one mile away from Publix and commercial development with many new restaurants.
$2,550
3Bedroom(s)
3Bathroom(s)
1,725Sqft

7621 Sutherton Ln, Windermere, Florida 34786

Residential Lease For Rent

MY REALTY GROUP, LLC.
One or more photo(s) has been virtually staged. Discover your new home at 7621 Suthertone Lane, nestled in the heart of Windermere’s charming Wickham Park community.
$2,500
3Bedroom(s)
3Bathroom(s)
1,520Sqft

12910 Calderdale Ave, Windermere, Florida 34786

Residential Lease For Rent

SIMS REALTY LLC
Townhome in Wickham Park. End unit with Three Bedrooms, Two and one half baths. Kitchen has 42" wood cabinets, All Appliances, Granite Counter Tops and opens to the Living/Dinning area. All bedrooms are on the second floor, Master suite has a walk in closet with organizer, bath has double vanity and shower. Laundry closet on second floor. The Private courtyard leads to the two car garage.
$2,500
3Bedroom(s)
3Bathroom(s)
1,545Sqft

7452 Leighside Dr, Windermere, Florida 34786

Residential Lease For Rent

LJL REAL ESTATE, INC.
Fantastic Location! Well Maintained Windermere townhome located in Lake Burden. Conveniently, Located to some of the Orlandos finest dinning and shopping areas. Also a quick drive to Winter Garden village, Disney World, Golf Courses and the up and coming Hamlin at Independence parkway. Home with 3 bedrooms and 2.5 baths, master bedroom is located downstairs with a walk in closet.
$2,500
3Bedroom(s)
3Bathroom(s)
1,910Sqft

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.
$2,450
3Bedroom(s)
3Bathroom(s)
1,840Sqft

8145 Serenity Spring Dr #ge, Windermere, Florida 34786

Residential Lease For Rent

SUNNY 365 REALTY GROUP
Beautiful townhome 3 BED, 2.5 BATH, 1 CAR GARAGE in resort style gated community. Stainless steel kitchen appliances, washer & dryer, upgraded wood cabinets, granite kitchen counter tops. All three bedrooms are upstairs, where there is carpet in the bedrooms and tile in the bathrooms & laundry.
$2,450
3Bedroom(s)
3Bathroom(s)
1,512Sqft

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)
Garage Door OpenerParking(s)
1,751Sqft

7351 Millstone St, Windermere, Florida 34786

Residential Lease For Rent

FRONTLINE FLORIDA REALTY, INC.
Beautiful Unfurnished 3 bedroom 2 and a half bath townhome in the best location in entire community! This upgraded, sparkling clean unit with stainless steel appliances, Fridge, Washer and Dryer.
$2,400
3Bedroom(s)
2Bathroom(s)
Garage Faces RearParking(s)
1,510Sqft

8716 Danforth Dr, Windermere, Florida 34786

Residential Lease For Rent

BEST ORLANDO PROPERTY MANAGEMENT LLC
Come view this Windermere 2 story townhome located just 10 minutes from Disney! This property has two master en-suites on the second floor. On the first floor you will find an extra bathroom, laundry and an open kitchen with plenty of natural light. The kitchen and dining areas include large wood cabinets and an island.
$2,350
2Bedroom(s)
3Bathroom(s)
1,360Sqft

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

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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