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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8500 Iron Mountain Trl, Windermere, Florida 34786

Residential Lease For Rent

TRUSTHOME PROPERTIES INC
Check out this beautiful townhome. The primary bedroom is on the first floor, with an ensuite bathroom with dual sinks and a large shower. The kitchen has 42" upper cabinets, double ovens, lots of storage, an eat-in space, and an island. There is also a guest powder room. There is a nice private back patio/courtyard area, in between the home and the 2-car garage.
$2,800
3Bedroom(s)
3Bathroom(s)
1,878Sqft

13333 Gorgona Isle Dr, Windermere, Florida 34786

Residential Lease For Rent

WRA BUSINESS & REAL ESTATE
Experience refined living in the heart of Windermere within a peaceful and exclusive community surrounded by conservation areas and natural beauty. This elegant residence offers 3 bedrooms and 2.5 bathrooms and features a generously sized private balcony—perfect for outdoor gatherings, relaxation, or enjoying serene views.
$2,800
3Bedroom(s)
3Bathroom(s)
1,779Sqft

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

13767 Beringer Street, Windermere, Florida 34786

Residential Lease For Rent

EXP REALTY LLC
This gorgeous 3 beds and 2/1 baths townhome features a fenced patio, walkway to garage, front porch, beautiful landscaping and pond views. The front of the unit has a quiet courtyard setting which is the perfect backdrop for when you are sitting in your front porch enjoying the water view.
$2,800
3Bedroom(s)
3Bathroom(s)
1,913Sqft

12508 Cragside Lane, Windermere, Florida 34786

Residential Lease For Rent

LEGENDS REALTY
4/2.
$2,750
4Bedroom(s)
3Bathroom(s)
2,392Sqft

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.
$2,750
3Bedroom(s)
3Bathroom(s)
1,912Sqft

12976 Borland St, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY LLC
A beautifully maintained townhome in the Wickham Park community of Windermere offers a comfortable living experience. The property features three bedrooms, two bathrooms, and a laundry closet on the second floor. Additionally, a half bathroom is available on the first floor for guest convenience.
$2,700
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,428Sqft

7601 Ripplepointe Way, Windermere, Florida 34786

Residential Lease For Rent

ANA TEIXEIRA REALTY
Live in one of Windermere’s most desirable communities! You cannot miss this lovely and beautifully maintained townhome in Windermere, Lake Burden. Spacious 3 bedroom, 3 1/2 bath with modern paint color at the walls, and ceramic flooring downstairs. Extra space at the first floor that could be used as office, TV room or play area. Amazing storage spaces, and all windows with blinds.
$2,700
3Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
1,881Sqft

Windermere, FL 34786

Residential Lease For Rent

WRA BUSINESS & REAL ESTATE
Beautiful Corner Unit in Ashlin Park, an excellent opportunity to live in the heart of Windermere, in front of a quiet pond. Top rated schools, bike trails, parks, community pool, Club house and playground. Tile flooring throughout first floor, carpet on the stairs and on the second floor. The home offers an open floor plan with upgrades and stainless-steel appliances, granite counter tops.
$2,700
3Bedroom(s)
3Bathroom(s)
CoveredParking(s)
1,584Sqft

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.
$2,695
3Bedroom(s)
2Bathroom(s)
Garage Door OpenerParking(s)
2,023Sqft

11320 Jasper Kay Terrace, Windermere, Florida 34786

Residential Lease For Rent

SPRING REALTY ONE LLC
Great END unit 3 bedroom, 2.5 bath, 2 car garage townhome right across the street from the pool near the heart of Windermere. The owner took great care and called this home for 5 years while providing several upgrades. This “End unit” means you have a lot more windows for natural light and side views.
$2,685
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,881Sqft

8326 Bryce Canyon Ave, Windermere, Florida 34786

Residential Lease For Rent

SPECIALIZED PROPERTY MANAGEMENT
SPECIAL $200 OFF THE 1ST MO RENT IF YOU SIGN A LEASE BEFORE 11/30 WITH A 2 YEAR LEASE. Step into elegance and comfort with this stunning 3-bedroom, 2.5-bathroom home nestled in the heart of Windermere.
$2,675
3Bedroom(s)
3Bathroom(s)
1,825Sqft
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