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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6920 Helmsley Cir, Windermere, Florida 34786

Residential Lease For Rent

CHARLES RUTENBERG REALTY ORLANDO
Beautiful One-Story Home in Windermere. The Perfect Place to Call Home! Discover comfort and elegance in this stunning single-story home located in the highly desirable community of Windermere. Featuring 3 spacious bedrooms and 2 full bathrooms, this property combines modern style with everyday functionality.
$3,100
3Bedroom(s)
2Bathroom(s)
2,156Sqft
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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.
$3,100
4Bedroom(s)
4Bathroom(s)
2,600Sqft
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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
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13094 Kegan St, Windermere, Florida 34786

Residential Lease For Rent

PM ELITE REALTY LLC
Beautifully remodeled home for rent in the highly desirable community of Windermere Sound! ? This spacious property offers 3 bedrooms, 2.5 bathrooms, and a bright open layout perfect for modern living. The updated kitchen features new appliances, quartz countertops, and elegant finishes.
$3,000
3Bedroom(s)
3Bathroom(s)
2,203Sqft
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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.
$3,000
3Bedroom(s)
3Bathroom(s)
1,852Sqft
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8153 Jailene Dr, Windermere, Florida 34786

Residential Lease For Rent

YORK MILLS REALTY LLC
Move-in Ready. GREAT HOME in Berkshire Park Community at WINDERMERE! Cul-De-Sac. Conservation Lot without rear neighbors! This is desirable 4 bedroom, 3 full bath, Oversized Screened Patio and Backyard! Open floor plan. Upgraded kitchen package, subway tile backsplash, granite counter tops, stainless steel appliance. Large master bedroom with french door to bath, walk-in closet.
$3,000
4Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
2,286Sqft
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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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13353 Overstreet Road, Windermere, Florida 34786

Residential Lease For Rent

CINO INTERNATIONAL INC
VACANT !! Downstairs has all tiled floors, and a private study or in-law bedroom. It oversees the front porch. Kitchen has granite counter top and a large island that can be used for breakfast bar. It opens up to the Great Room and provides a best place for family and friends' gathering. Upstairs has a large master bedroom, and three bedrooms.
$2,950
5Bedroom(s)
3Bathroom(s)
2,701Sqft
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7231 Rambling Water Way, Windermere, Florida 34786

Residential Lease For Rent

REAL ESTATE FIRM OF ORLANDO
Beautiful 3/4 Bedroom home with 2 1/2 Bath. Fenced Patio, kitchen made for entertaining, along with spacious panty and amble sized Family Room, additional bedroom downstairs, other bedrooms downstairs. 4th Bedroom can be Home Office, study, or formal dining room. Ashlin Park is one of the best locations in Windermere, convenient to the 535 road and close to shopping and restaurants.
$2,950
3Bedroom(s)
3Bathroom(s)
2,193Sqft
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Windermere, FL 34786

Residential Lease For Rent

INT'L PROFESSIONAL REALTY INC
Townhouse in gated community near Disney. furnished, 4 bed/2.5 bathroom 2 cars garage. Water, basic cable included.
$2,950
4Bedroom(s)
3Bathroom(s)
2,028Sqft
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8639 Via Trieste Dr, Windermere, Florida 34786

Residential Lease For Rent

CANVAS REAL ESTATE
Discover this spacious 4-bedroom, 3.5-bathroom townhouse located in the sought-after area of Windermere. This elegant two-story residence has a highly functional design. The main floor features the primary suite with a closet and en-suite bathroom, along with a convenient half bath.
$2,950
4Bedroom(s)
4Bathroom(s)
CoveredParking(s)
2,464Sqft
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12647 Arley Dr, Windermere, Florida 34786

Residential Lease For Rent

CENTURY 21 CARIOTI
Welcome to Lakes of Windermere. This spacious executive four-bedroom, two-and-a-half-bath home is in a great location. The home features a new roof replaced in May 2025, and a new HVAC system installed in June 2025, whilst the exterior is scheduled to be painted. The property has been decorated and is ready for occupancy, except for carpets, which will be steam cleaned before move-in.
$2,900
4Bedroom(s)
3Bathroom(s)
2,460Sqft
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