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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11446 Jasper Kay Ter #309, Windermere, Florida 34786

Residential For Sale

CHARLES RUTENBERG REALTY ORLANDO
Welcome to Lakeside! This well maintained 2 bedroom/2 bath unit is located on the third floor with no upstairs neighbors! You'll be impressed by the size of the living area in this light and bright unit which includes a good size living room with separate dining area and a spacious kitchen with a breakfast bar and a tiled backsplash.
$295,000
2Bedroom(s)
2Bathroom(s)
AssignedParking(s)
1,161Sqft

9343 Tibet Pointe Cir, Windermere, Florida 34786

Residential Lease For Rent

LA ROSA REALTY LLC
Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry.
$39,500
7Bedroom(s)
10Bathroom(s)
OversizedParking(s)
8,362Sqft

11103 Bridge House Rd, Windermere, Florida 34786

Residential Lease For Rent

THE SIMON SIMAAN GROUP
Welcome to this extraordinary 5 bedroom, 8 bathroom waterfront estate located in one of Windermere’s most exclusive communities, Lake Butler Sound. This prestige 24/7 man-gated neighborhood offers unmatched privacy, security, and luxury living.
$35,000
5Bedroom(s)
8Bathroom(s)
DrivewayParking(s)
8,443Sqft

3999 Isabella Cir, Windermere, Florida 34786

Residential Lease For Rent

DELUCA REAL ESTATE SERVICES CORP
AVAILABLE IN OCTOBER - Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort.
$19,900
6Bedroom(s)
8Bathroom(s)
6,881Sqft

6115 Orta Ct, Windermere, Florida 34786

Residential Lease For Rent

BHHS FLORIDA REALTY
Extravagant and Luxurious Lakefront Estate located within the exclusive gated Waterstone Community in Windermere. Expansive open floorplan with stunning wood and porcelain/ceramic throughout. The Primary Bedroom is located on the ground floor and features a private patio with scenic views of the lake as well as a custom Walk-In closet and an amazing primary bathroom.
$18,500
6Bedroom(s)
8Bathroom(s)
Garage Door OpenerParking(s)
6,853Sqft

4303 Isabella Cir, Windermere, Florida 34786

Residential Lease For Rent

WRA BUSINESS & REAL ESTATE
Best Value in Casabella — Fully Furnished & Move-In Ready! Step into effortless luxury in this beautifully furnished residence, where elegant design meets everyday comfort. Soaring windows fill the space with natural light, highlighting stylish interiors and thoughtfully curated furnishings throughout.
$18,000
7Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
4,834Sqft

6844 Valhalla Way, Windermere, Florida 34786

Residential Lease For Rent

CHARLES RUTENBERG REALTY ORLANDO
Beautiful and fully furnished home in Keene's Pointe golf community. Guard gated community. A Tuscan style luxury home with a large covered back patio with fireplace and large pool overlooking the 14th green Bear Club. Master and extra suite on first floor and three more suites upstairs. This house has a very big loft, perfect for entertaining.
$15,000
5Bedroom(s)
6Bathroom(s)
5,339Sqft

3120 Downs Cove Rd, Windermere, Florida 34786

Residential Lease For Rent

COMPASS FLORIDA LLC
Amazing opportunity to lease this stunning Butler Chain lakefront estate nestled on over 2 acres of meticulously manicured grounds. From the moment you enter this spectacular property, you are greeted by expansive views of Lake Down, visible from nearly every room.
$15,000
6Bedroom(s)
7Bathroom(s)
8,942Sqft

4012 Isabella Cir, Windermere, Florida 34786

Residential Lease For Rent

METROPOLITAN R.E SOLUTIONS INC
Step into elegance! This beautifully designed luxury home in Casabella, Windermere, offers the perfect blend of comfort and sophistication. Casabella features 79 exclusive luxury homes and private gated entry.
$14,800
6Bedroom(s)
9Bathroom(s)
CoveredParking(s)
7,337Sqft

7848 Ficquette Road, Windermere, Florida 34786

Residential Lease For Rent

JOHN SILVA REALTY & ASSOCIATES
Welcome to this stunning 5-bedroom, 4-bathroom house located in the desirable Windermere, FL. This spacious home offers a comfortable and luxurious living experience. The private pool is perfect for those hot summer days, providing a refreshing oasis right in your backyard.
$13,500
5Bedroom(s)
4Bathroom(s)
4,015Sqft

6219 Tiroco Way, Windermere, Florida 34786

Residential Lease For Rent

CENTURY 21 CARIOTI
Luxurious furnished house for RENT with 7 bedrooms and 5/1 bathrooms, huge Resort like pool and patio located in the elegant gated community of Waterstone. Two story ceilings, an enormous crystal chandelier, wood floors and an open wood staircase defines the foyer and living room.
$13,500
7Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,221Sqft

11051 Coniston Way, Windermere, Florida 34786

Residential Lease For Rent

SOUTHERN REALTY GROUP LLC
Highly sought after custom home in Reserve at Lake Butler Sound. Beautiful iron arched double doors welcome you to an open floor plan with travertine floors and a view to the pool/lanai. Wrought iron chandeliers adorn the entry and spacious dining area. Upgraded features are aplenty in this beautiful home including top-of-the-line appliances, 2 gas fireplaces, and high ceilings.
$13,000
5Bedroom(s)
6Bathroom(s)
Garage Door OpenerParking(s)
5,498Sqft
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