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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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

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

9134 Sabal Palm Cir, Windermere, Florida 34786

Residential Lease For Rent

KELLER WILLIAMS REALTY AT THE PARKS
WINDERMERE **RENT INCLUDES, LAWN, POOL and PEST. Located in the highly desirable SILVER WOODS neighborhood, this stunning one-story 4BR/2.5BA POOL HOME offers 2,026 sq. ft. of updated living space and is ready for you to call home! Step inside to soaring ceilings, sleek laminate flooring throughout, and sliding glass doors showcasing beautiful views of the pool and backyard retreat.
$3,300
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,026Sqft

12621 Salomon Cove Dr, Windermere, Florida 34786

Residential Lease For Rent

MAGICMIND REALTY LLC
Welcome to this move-in ready home in sought-after Westside Village, offering a FLEXIBLE FLOOR PLAN and SEPARATE 1-BEDROOM IN-LAW SUITE above the garage — perfect for guests, rental income, or multi-generational living.
$3,300
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,604Sqft

7119 Beek St, Windermere, Florida 34786

Residential Lease For Rent

MACKEN REALTY INC
Welcome to this beautifully maintained single-family home in the highly sought-after Windermere Terrace Community. Perfectly located near Disney Parks, premier shopping, and A+ rated schools, this home offers the ideal blend of comfort, style, and convenience. Bright and airy open-concept floor plan filled with natural light. This home features 3 spacious bedrooms and 2 full bathrooms.
$3,300
3Bedroom(s)
2Bathroom(s)
1,910Sqft

6971 Tettenhall Ln, Windermere, Florida 34786

Residential Lease For Rent

PREMIUM PROPERTIES REAL ESTATE
$500 Discount off of Second Month's rent! Discover this stunning 2-story, 4-bedroom, 3-bathroom home. Enjoy breathtaking views of the fountain pond from the covered front lanai, beautifully accented with stacked stone columns. Step inside to be welcomed by arched walkways, wood-paneled walls, and elegant wood laminate flooring.
$3,295
4Bedroom(s)
3Bathroom(s)
2,805Sqft

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.
$3,250
3Bedroom(s)
3Bathroom(s)
2,043Sqft

13754 Amelia Pond Dr, Windermere, Florida 34786

Residential Lease For Rent

JOY ESTATE ENTERPRISE INC
Beautiful 4-bedroom, 2.5-bathroom home with office and serene pond view located in the highly desirable Summerport Trail community of Windermere. Zoned for top-rated schools, this spacious two-story home features a high-ceiling family room with tile flooring throughout the main living areas. The first floor includes a private office and a convenient half bath.
$3,200
4Bedroom(s)
3Bathroom(s)
2,829Sqft

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

13786 Summer Harbor Court, Windermere, Florida 34786

Residential Lease For Rent

LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
Welcome to Summerport Trail community of Windermere, nightly Disney fireworks display from your front porch. Spacious layout with tile flooring in the main living areas. The main floor includes a half bath. The large kitchen boasts granite countertops, a breakfast bar, appliance package, a pantry, and ample counter space,looking into the dining area and great room.
$3,100
4Bedroom(s)
3Bathroom(s)
2,236Sqft

4542 Blue Major Dr, Windermere, Florida 34786

Residential Lease For Rent

CINO INTERNATIONAL INC
VACANT! Great location! Great Home! Move in this Great home inside the lovely SUMMERPORT/WINDERMERE community. This house is full of upgrades and is an Energy Star certified home. Downstairs has all tiled floor and new laminate. Kitchen has all fully appliances and granite counter top. You can also enjoy Disney firework at night. Upstairs has a large master bedroom, and three bedrooms.
$3,100
4Bedroom(s)
3Bathroom(s)
2,618Sqft
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