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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11819 Vermillion Ave, Windermere, Florida 34786

Residential Lease For Rent

CENTENNIAL REALTY GROUP LLC
Gorgeous 3-bedroom, 2.5-bathroom Townhouse for rent with 1,760 square feet of modern elegance and thoughtful design. The modern finishes throughout the home exude sophistication. Open layout of the living room, dining room and kitchen, which is ideal for entertaining family and friends.
$2,800
3Bedroom(s)
3Bathroom(s)
1,760Sqft
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805 Oakdale St, Windermere, Florida 34786

Residential Lease For Rent

PREMIER MANAGEMENT GROUP INC
Live amongst the oaks in this 3BD/2BA large corner lot home in the heart of Olde Windermere. Just a short walk to the historic downtown of Windermere. Stainless steel appliances, granite countertops with wine racks! Area boasts parks, tennis courts, public library, full time police security! Come home to "Olde Windermere"! Lawn care included.
$2,800
3Bedroom(s)
2Bathroom(s)
1,710Sqft
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13767 Beringer Street, Windermere, Florida 34786

Residential Lease For Rent

EXP REALTY LLC
This gorgeous 3 beds and 2/1 baths townhome features a fenced patio, walkway to garage, front porch, beautiful landscaping and pond views. The front of the unit has a quiet courtyard setting which is the perfect backdrop for when you are sitting in your front porch enjoying the water view.
$2,800
3Bedroom(s)
3Bathroom(s)
1,913Sqft
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10600 Reams Rd, Windermere, Florida 34786

Residential Lease For Rent

PREMIUM REALTY GROUP USA
LOCATION! LOCATION! LOCATION! TOP RATED SCHOOLS. NO CARPET. This beautiful property is just a 3-minute walk to Bay Lake Elementary, offering unmatched convenience for families. Enjoy easy access to SR-535, shopping, dining, major theme parks, and all the best that the Horizon West / Disney area has to offer.
$2,799
3Bedroom(s)
3Bathroom(s)
1,845Sqft
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12508 Cragside Lane, Windermere, Florida 34786

Residential Lease For Rent

LEGENDS REALTY
4/2.
$2,750
4Bedroom(s)
3Bathroom(s)
2,392Sqft
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10714 Reams Rd, Windermere, Florida 34786

Residential Lease For Rent

WRA BUSINESS & REAL ESTATE
Beautiful 3-bedroom, 2.5-bath home located in the desirable Windermere Trails community. This well-maintained property features a spacious open-concept floor plan with brand-new stainless steel appliances and abundant natural light. All bedrooms are located upstairs, along with a versatile loft area ideal for a home office, playroom, or media space.
$2,750
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,889Sqft
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8623 Via Trieste Dr, Windermere, Florida 34786

Residential Lease For Rent

THE REAL ESTATE COLLECTION LLC
AVAILABLE NOW for quick move-in. Charming corner townhome with 4 bedrooms, 3.5 bath and a loft area. Upon entering you are greeted with an open living and stunning kitchen. Kitchen features granite countertops, stainless steel appliances and walk-in pantry. Downstairs master with ensuite bath, dual vanities, spacious walk-in closet. Courtyard area leads to two car garage.
$2,700
4Bedroom(s)
4Bathroom(s)
Garage Door OpenerParking(s)
2,464Sqft
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7654 Fairgrove Ave, Windermere, Florida 34786

Residential Lease For Rent

OLYMPUS EXECUTIVE REALTY INC
Great opportunity to live in a beautiful 4 bedroom / 2.5 bathroom / 2 story Townhome in the desirable community of Windermere Sound!!! Master bedroom is located on the first floor and all remaining bedrooms are located on the second floor of the home. Kitchen features Breakfast Bar, Granite Countertops and Stainless Steel Appliances.
$2,700
4Bedroom(s)
3Bathroom(s)
1,866Sqft
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11661 Black Rail St, Windermere, Florida 34786

Residential Lease For Rent

JOY ESTATE ENTERPRISE INC
well located 4 bedroom house. Great community with pool and high rated school. Convenience location with lot of amenities around it.
$2,700
4Bedroom(s)
3Bathroom(s)
2,139Sqft
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7448 Leighside Dr, Windermere, Florida 34786

Residential Lease For Rent

ALTIS REALTY
Live in one of Windermere’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath townhome offers a spacious open-concept layout perfect for comfortable living. The kitchen features granite countertops, stainless steel appliances, 42” solid wood cabinets, and a generous amount of storage.
$2,700
3Bedroom(s)
3Bathroom(s)
1,881Sqft
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11320 Jasper Kay Terrace, Windermere, Florida 34786

Residential Lease For Rent

SPRING REALTY ONE LLC
Great END unit 3 bedroom, 2.5 bath, 2 car garage townhome right across the street from the pool near the heart of Windermere. The owner took great care and called this home for 5 years while providing several upgrades. This “End unit” means you have a lot more windows for natural light and side views.
$2,685
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,881Sqft
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1047 Lascala Dr, Windermere, Florida 34786

Residential Lease For Rent

INGRAM REALTY SERVICES LLC
Beautiful 3-Bedroom, 2.5-Bath Home in Gated Belmere Village – Windermere Welcome to this stunning single-story home in the highly sought-after gated community of Belmere Village. Offering spacious living and thoughtful design, this residence includes 3 bedrooms, 2.5 baths, and a versatile office/den plus a built-in hallway desk area—perfect for homework, crafts, or a home workspace.
$2,675
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,852Sqft
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