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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11551 Via Lucerna Cir, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA REALTY EXCHANGE LLC
Light and bright, refreshed 4 bedroom 2.5 bath single family home for rent in gated Belmere community. Close to the 408, turnpike, all amenities and downtown Windermere. No carpets here just tile floors throughout. Kitchen is open to family room which has sliders to the beautifully landscaped completely fenced in backyard.
$3,000
4Bedroom(s)
3Bathroom(s)
DrivewayParking(s)
2,206Sqft

13040 Overstreet Rd, Windermere, Florida 34786

Residential Lease For Rent

CHARLES RUTENBERG REALTY ORLANDO
Welcome to this gorgeous 3-bedroom, 2.5-bath single-family home located in the highly desirable Windermere area. Situated within top-rated school zones, this home offers both comfort and convenience. The kitchen features granite countertops and opens to a functional living space perfect for everyday living and entertaining.
$3,000
3Bedroom(s)
3Bathroom(s)
2,203Sqft

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, 2 car garage and approximately 2,659 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.
$2,989
4Bedroom(s)
4Bathroom(s)
2,659Sqft

12653 Arley Dr, Windermere, Florida 34786

Residential Lease For Rent

WATSON REALTY CORP
This beautiful 4 bedroom, 2 bathroom home is located in the wonderful subdivision of Lakes of Windermere. This home is spacious with nearly 2,300 square feet. The large home features an open floorplan with upgraded dark cherry cabinets along with black kitchen appliances, neutral tile and carpet throughout, a master bathroom with double vanities and separate shower and tub.
$2,975
4Bedroom(s)
2Bathroom(s)
2,300Sqft

7505 Fairgrove Ave, Windermere, Florida 34786

Residential Lease For Rent

METROPOLITAN R.E SOLUTIONS INC
Beautiful two-story home in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,980 sq. ft. of elegant living space. The primary suite is located upstairs, while bedrooms 2 and 3 share a convenient Jack & Jill bathroom.
$2,900
3Bedroom(s)
3Bathroom(s)
1,980Sqft

7681 Fordson Ln, Windermere, Florida 34786

Residential Lease For Rent

REILE REALTY CORP
Experience modern, energy-efficient living with SOLAR PANELS that provide sustainable power and an exceptionally low electric bill! This beautiful townhome for rent is located in the highly desirable community of Windermere Sound. Offering 4 bedrooms and 2.5 bathrooms, this spacious property features ceramic tile flooring in the main areas and carpet in the bedrooms for added comfort.
$2,900
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,997Sqft

11842 Silverlake Park Dr, Windermere, Florida 34786

Residential Lease For Rent

AGENT TRUST REALTY CORPORATION
Welcome to this stunning 4-bedroom, 2.5-bath home located on a desirable corner lot in one of Windermere’s most sought-after communities. The open living and dining areas flow seamlessly, ideal for both everyday living and entertaining.
$2,900
4Bedroom(s)
3Bathroom(s)
2,115Sqft

8174 Enchantment Dr #1601, Windermere, Florida 34786

Residential Lease For Rent

MS LAND & BUILDING LLC
Welcome to your new home in beautiful Windermere! This charming 3 bedroom and 2.5 bath townhome offers a bright and open layout designed for comfort and everyday living. The spacious living room flows seamlessly into the dining area and kitchen, creating the perfect space for gatherings. The kitchen features stainless steel appliances and some cabinet space.
$2,900
3Bedroom(s)
3Bathroom(s)
1,852Sqft

5333 Keenes Pheasant Drive, Windermere, Florida 34786

Residential Lease For Rent

LIFESTYLE INTERNATIONAL REALTY
Welcome Home to this gorgeous MOVE IN ready Summerport Townhome! This home is conveniently located right in front of Keene's Elementary school, directly to your left is a plaza with a nail salon, Foxtail Coffee and Kelly's Ice Cream and more. A park is within 5 minutes walking distance from the house, making outings in the evening enjoyable with everything the community has to offer.
$2,900
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,461Sqft

12337 Via Derna Pl, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA CONNEXION PROPERTIES
Available now for quick move-in! This beautifully updated corner townhome offers 4 bedrooms, 3.5 bathrooms, and a versatile loft area, combining comfort, style, and an exceptional location.
$2,890
4Bedroom(s)
4Bathroom(s)
1,936Sqft

8320 Iron Mountain Trl, Windermere, Florida 34786

Residential Lease For Rent

TRANSCEND REALTY
Welcome to this beautifully updated townhouse in the highly sought-after Windermere, FL area, offering serene lake views and a peaceful, picturesque setting. This 4-bedroom, 2.5-bath home has been fully refreshed with new interior paint and modern vinyl flooring, creating a clean, stylish, and low-maintenance living space.
$2,887
4Bedroom(s)
3Bathroom(s)
1,766Sqft

8160 Iron Mountain Trl, Windermere, Florida 34786

Residential Lease For Rent

GECKO REALTY, INC
Welcome to this beautifully designed residence in the highly sought-after Windermere Trails community. Combining modern style with everyday functionality, this home offers an open-concept floor plan and high-end finishes throughout.
$2,875
3Bedroom(s)
3Bathroom(s)
Garage Faces RearParking(s)
2,009Sqft
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