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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2113 Grove Point Ln, Windermere, Florida 34786

Residential Lease For Rent

THE FLORIDA LOUNGE REALTY LLC
Discover this stunning rental home located in the Waterford Pointe community on Lake Roberts. Enjoy exclusive access to a private community boat ramp in a serene, gated neighborhood. This beautifully furnished residence features new bamboo flooring, high-end appliances, and elegant décor throughout.
$5,500
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,830Sqft

11905 Camden Park Dr, Windermere, Florida 34786

Residential Lease For Rent

KEENE'S POINTE REALTY
This rare opportunity for a lovely two-story rental home in Keene's Pointe is now available to show and move in ready today - October 1, 2025. Terrific floor plan boasts 4BR/4.5 Baths + office + bonus room and a 3 Car Garage. Primary Suite is located on the man floor with all other bedrooms on the second floor along with the bonus room.
$5,000
5Bedroom(s)
5Bathroom(s)
Garage Door OpenerParking(s)
3,483Sqft

9005 Reflection Pointe Dr, Windermere, Florida 34786

Residential Lease For Rent

KARDOSH REALTY
Spacious 5-bedroom, 3-bath home in Windermere Trails, built in 2015 and offering approximately 3,783 sq ft. The floor plan includes an open kitchen with granite countertops, a step-up island, and walk-in pantry, integrated with the main living area. The first-floor primary suite features dual sinks, granite counters, garden tub, and separate shower.
$5,000
5Bedroom(s)
4Bathroom(s)
3,793Sqft

13106 Orange Isle Dr, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA CONNEXION PROPERTIES
Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort.
$5,000
5Bedroom(s)
5Bathroom(s)
DrivewayParking(s)
3,312Sqft

7508 Lake Albert Dr, Windermere, Florida 34786

Residential Lease For Rent

MS LAND & BUILDING LLC
Don't miss this custom-built 4-bedroom, 3.5-bath Windermere Pool Home – beautifully updated and move-in ready! Conveniently located near theme parks, shopping, and top-rated schools, this stunning property offers a perfect blend of style, comfort, and practicality.
$4,800
4Bedroom(s)
4Bathroom(s)
3,059Sqft

11837 Cave Run Ave, Windermere, Florida 34786

Residential Lease For Rent

US SQUARE REAL ESTATE
Windermere Trails Home Across from Park | A-Rated Schools | Experience the best of Central Florida living in this beautiful 4-bedroom, 3.5-bathroom home located in the highly desirable Windermere Trails community. Perfectly situated on a quiet street directly across from the community park and playground, this home offers a rare combination of privacy, convenience, and lifestyle amenities.
$4,700
4Bedroom(s)
4Bathroom(s)
3,407Sqft

6926 Cucamelon Ct, Windermere, Florida 34786

Residential Lease For Rent

CENTURY 21 CARIOTI
A rare opportunity to lease a beautiful home either furnished or unfurnished with solar panels! This property shines with lifestyle features in the very sought-after neighborhood of Sanctuary Lakes in Windermere upon entering, this home is luxury, convenience and the genuine feeling of home with integrated smart home features.
$4,500
5Bedroom(s)
4Bathroom(s)
DrivewayParking(s)
2,872Sqft

14409 Crest Palm Ave, Windermere, Florida 34786

Residential Lease For Rent

RENT A FLORIDA HOME
Brand-New 2025 Windermere Home with Loft, Bonus Room, and Contemporary Design Experience luxurious living in this expansive 6-bedroom, 3.5-bath, two-story home, featuring a bright and airy open-concept layout that seamlessly connects the gourmet kitchen, inviting family room, and elegant dining area.
$4,500
6Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,764Sqft

4345 Saltmarsh Sparrow Dr, Windermere, Florida 34786

Residential Lease For Rent

ICON REALTY ASSOCIATES INC
WELCOME HOME to Summerport! HUGE PRICE REDUCTION!! This stunning 6-bedroom, 5.5-bathroom residence is now available for rent in the highly desirable Summerport neighborhood—zoned for top-rated A+ schools! Step inside and enjoy a thoughtfully designed split two-story floor plan with plenty of room for family and entertaining.
$4,500
6Bedroom(s)
6Bathroom(s)
DrivewayParking(s)
3,389Sqft

12025 Lake Butler Blvd, Windermere, Florida 34786

Residential Lease For Rent

MCO REALTY
Welcome to your 4-bedroom, 3-bathroom, three car garage sanctuary! As you open your beautiful door, expect to be wowed at your perfect masterpiece. You are greeted by your huge family room leading into the living room with a wood burning fireplace. Your living room boasts lighting through your rear doors leading to your gorgeous, screen enclosed patio.
$4,500
4Bedroom(s)
3Bathroom(s)
2,588Sqft

11994 Mckinnon Rd, Windermere, Florida 34786

Residential Lease For Rent

CENTURY 21 CARIOTI
Welcome home to an elegant and spacious 4 bedroom, 3 full bathroom, 2 half bathroom home located in the highly sought-after town of Windermere, it offers the perfect blend of privacy, comfort, and opportunity all in one of Central Florida?s most desirable communities. Enjoy the outdoor patio and pool with ample space to unwind and entertain.
$4,500
4Bedroom(s)
5Bathroom(s)
2,450Sqft

14415 Crest Palm Ave, Windermere, Florida 34786

Residential Lease For Rent

RENT A FLORIDA HOME
Contemporary 2025 Windermere Home with Loft, Bonus Room, and Stylish Upgrades! Internet and WiFi Included! Step into elegant living in this expansive 6-bedroom, 3.5-bath, two-story home, featuring a light-filled open-concept layout that effortlessly connects the gourmet kitchen, welcoming family room, and refined dining area.
$4,500
6Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
3,764Sqft
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