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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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

7448 Ella Ln, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY LLC
Experience the perfect mix of elegance, comfort, and versatility in this 4-bedroom, 2.5-bathroom home in the Beautiful Windermere community. Step inside to discover this well maintained property with designed living spaces, open layouts from room to room. The spacious open-concept layout goes from the spacious and well equipped kitchen to the living and dining areas.
$3,500
4Bedroom(s)
3Bathroom(s)
CoveredParking(s)
2,623Sqft

11530 Charnock Drive, Windermere, Florida 34786

Residential Lease For Rent

GLASSTONE GROUP INC
Enjoy the opportunity to lease this beautiful and spacious 4-bedroom, 3-bathroom home located in the highly sought-after Westside Village community in Windermere. With a modern open-concept layout, this home offers plenty of space for comfortable living and effortless entertaining.
$3,400
4Bedroom(s)
3Bathroom(s)
2,212Sqft

8631 Crescendo Ave, Windermere, Florida 34786

Residential Lease For Rent

REALTY HUB
Family-friendly 4 Bedrooms home in prime location, features a spacious kitchen with expansive center island, tons of cabinet space, granite countertops, walk in pantry and eat in dining. There is a den/office for all your organizing needs. A private guest suite with private full bath on main floor.
$3,350
4Bedroom(s)
4Bathroom(s)
2,876Sqft

7241 Sunny Meadow Aly, Windermere, Florida 34786

Residential Lease For Rent

B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE
This beautiful single-family residence FOR RENT offers the perfect combination of modern comfort and resort-style living. Great floorpan featuring 3 Bedrooms, 2-1/2 Bathroons and a great office. From the moment you arrive, you'll be captivated by the inviting atmosphere and community amenities, including a sparkling, resort-style pool—ideal for relaxing weekends.
$3,200
3Bedroom(s)
3Bathroom(s)
2,043Sqft

13954 Darchance Road, Windermere, Florida 34786

Residential Lease For Rent

CHARLES RUTENBERG REALTY ORLANDO
This beautiful 3 bedroom WITH DEN, 2.5 bath home with water/conservation views located at Enclave at Berkshire Park is ready for you! As you enter the home, you find a formal living room and dining room combo with hand scraped hardwood, including an open floor plan perfect for entertaining, with a kitchen and family room combination.
$3,200
3Bedroom(s)
3Bathroom(s)
2,234Sqft

7224 Halton Ct, Windermere, Florida 34786

Residential Lease For Rent

COLDWELL BANKER RESIDENTIAL RE
Welcome to this beautifully refreshed two-story home offering over 2,400 sq ft of living space in the desirable Enclave community in Windermere. The first floor features a functional layout with living and dining areas, a comfortable family room, and a kitchen equipped with stainless-steel appliances, a breakfast bar, big pantry and plenty of space for everyday living and entertaining.
$3,200
4Bedroom(s)
4Bathroom(s)
2,420Sqft

Windermere, FL 34786

Residential Lease For Rent

TAH FLORIDA LLC
Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 3.5 bathrooms, 3 car garage and approximately 2,745 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.
$3,169
4Bedroom(s)
4Bathroom(s)
2,745Sqft

13426 Chariho Ln, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY ORLANDO LLC
Welcome to this beautifully maintained 4-bedroom, 3-bath home with a loft and office located in a highly sought-after gated community in Windermere. This spacious residence offers a fresh, move-in-ready feel with fairly new carpeting throughout the stairs and second floor.
$3,150
4Bedroom(s)
4Bathroom(s)
2,600Sqft

12921 Cragside Ln, Windermere, Florida 34786

Residential Lease For Rent

WINDERMERE INTERNATIONAL REALTY
Great rental opportunity z in the Lakes of mid mirror. Solid flooring throughout. Pets allowed.
$3,100
4Bedroom(s)
2Bathroom(s)
2,151Sqft

8494 Iron Mountain Trail, Windermere, Florida 34786

Residential Lease For Rent

LIBERTY HOME SALES INC
Enjoy Windermere's finest living in this clean end unit townhome which is across the street from the park. Huge sidewalks for walking, running, and riding. Elementary school, Pre-K school, and Publix are within minutes of walking distance. Close proximity to restaurants, banks, and other business centers. Tenants will be provided personal key cards for the pool area.
$3,000
3Bedroom(s)
3Bathroom(s)
1,826Sqft

14217 Bridgewater Crossings Blvd, Windermere, Florida 34786

Residential Lease For Rent

WEICHERT REALTORS HALLMARK PRO
Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom.
$3,000
4Bedroom(s)
3Bathroom(s)
2,419Sqft
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