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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Windermere, Florida 34786

Residential Lease For Rent

ORLANDO REALTY & PROPERTY MGNT
Windermere 3 Bedrm 2 Car Garage Townhome Near Disney For Rent SEE TERMS Priced Low, Call Now! Very Clean Property, 2 Car Garage, Brick Pavered Backyard, Patio Granite Countertops, 42” Cabinets, Tile Flooring, Carpeted Bedrooms, Ceiling Fan In Many Rooms, COMMUNITY Pool! COMMUNITY Playground, JUST 35 MINUTES To Downtown Orlando, JUST 40 MINUTES To The Airport, JUST MINUTES To All Theme Parks,
$2,317
3Bedroom(s)
3Bathroom(s)
1,644Sqft
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8168 Boat Hook Loop #707, Windermere, Florida 34786

Residential Lease For Rent

TEAM DONOVAN
Welcome to this move in ready condo in the desirable Lakeside at Lakes of Windermere. This unscale condo community has everything. This first floor 3 bed 2 bath unit is located just across the street from the community clubhouse and pool. With close proximity to the Lakeside Village for shops, restaurants and grocery store, and only 15 mins to Disney.
$2,300
3Bedroom(s)
2Bathroom(s)
1,332Sqft
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8180 Boat Hook Loop #103, Windermere, Florida 34786

Residential Lease For Rent

TOP TEAM REALTY, LLC.
Great apartment for rent in the beautiful City of Windermere Orlando FL, 3 bedrooms 2 full Baths, corner unit on the first floor of the building, screened private patio, new paint throughout, spacious dining and living room area, large kitchen, moder tile and laminate flooring, fans in all bedrooms and living room, 2 parking spaces, water included.
$2,300
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,442Sqft
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8179 Maritime Flag St #210, Windermere, Florida 34786

Residential Lease For Rent

L & L REALTY GROUP
3 bedroom, 2 bath condo on second floor. Carpet in living areas. Large pantry in kitchen and second storage closet. Easy access to major road and minutes to Disney. Community offers many amenities. Open floor plan. W/D in unit.
$2,300
3Bedroom(s)
2Bathroom(s)
AssignedParking(s)
1,442Sqft
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8192 Boat Hook Loop #206, Windermere, Florida 34786

Residential Lease For Rent

SPRING REALTY ORLANDO
Great location in Windermere walking distance to restaurants and shopping. Great community with pool and fitness center. Second floor but elevator available. Split bedrooms. Washer/drier included. Wood floors in main living area.
$2,300
3Bedroom(s)
2Bathroom(s)
1,455Sqft
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11562 Amidship Ln #208, Windermere, Florida 34786

Residential Lease For Rent

ALFANO PROPERTY MANAGEMENT
Freshly updated three bedroom, two full bathroom condo at Lakeside at Lakes of Windermere. Second floor unit with elevator access in building. Tile and new laminate flooring, no carpet. Screened in balcony with sliding door access. Fully equipped kitchen and laundry closet with washer/dryer. Community features, beach volleyball courts, pool, and fitness center. Two car assigned parking.
$2,200
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,442Sqft
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11446 Jasper Kay Ter #303, Windermere, Florida 34786

Residential Lease For Rent

ALFANO PROPERTY MANAGEMENT
Updated three bedroom, two full bathroom condo at Lakeside at Lakes of Windermere. Third floor unit with elevator access in building. Tile and laminate flooring throughout entire unit. Screened in balcony with sliding door access. Fully equipped kitchen and laundry closet with washer/dryer. Great location, condition and price. Community features, beach volleyball courts, pool, and fitness center.
$2,200
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,442Sqft
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8156 Boat Hook Loop #303, Windermere, Florida 34786

Residential Lease For Rent

ALFANO PROPERTY MANAGEMENT
Third floor condo with three bedrooms, two full bathrooms at Lakeside at Lakes of Windermere. Private corner unit with elevator access in building. Tile in living area, and new laminate flooring in bedrooms, no carpet. Screened in balcony with sliding door access. Fully equipped kitchen with new kitchen appliances. Laundry closet with washer/dryer included. Entire interior was just repainted.
$2,200
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,442Sqft
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11377 Evesham Dr, Windermere, Florida 34786

Residential Lease For Rent

JAMIESON PROPERTIES, INC.
Available Now! Stunning 2BR/2.5BA in the desirable community of Preston Square in Windermere. The main level includes a Great Room that opens to a private brick-paver courtyard, ideal for entertaining. The kitchen boasts granite countertops, dinette area, and A half bath, laundry room with washer and dryer included, and access to the attached 2-car garage.
$2,200
2Bedroom(s)
3Bathroom(s)
Garage Faces RearParking(s)
1,385Sqft
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8271 Maritime Flag St #s, Windermere, Florida 34786

Residential Lease For Rent

MY REALTY GROUP, LLC.
Discover the charm of Windermere living with this 3-bedroom, 2.5-bath villa, designed for those who value comfort, convenience, and style. From the moment you enter, you’re welcomed into a bright and open living space that flows effortlessly into a dedicated dining area and a kitchen ready for both casual dinners and special gatherings.
$2,150
3Bedroom(s)
3Bathroom(s)
1,363Sqft
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7347 Millstone St, Windermere, Florida 34786

Residential Lease For Rent

BEST ORLANDO PROPERTY MANAGEMENT LLC
Offering a $500 move-in incentive if moved in by mid-November! Come view this 2 bed, 2.5 bath Windermere home located minutes from Disney, shopping, restaurants, Winter Garden Village, etc. On the first floor, you’ll find an open floor plan with a bright kitchen, living room, dining room, half bathroom, storage, and patio.
$2,150
2Bedroom(s)
3Bathroom(s)
1,374Sqft
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8264 Maritime Flag Street #1422, Windermere, Florida 34786

Residential Lease For Rent

BELLA VIEW REALTY LLC
Make this beautiful 2 bedroom, 2 bath condo the perfect space for your family. Located at Lakeside at Lakes of Windermere. This gated community is coveted for their amenities that includes a community pool, play area, fitness center, recreational facilities and more. It is close location to Orlando attractions such as Disney World and Universal. No pets and non-smoking unit, please.
$2,100
2Bedroom(s)
2Bathroom(s)
AssignedParking(s)
1,161Sqft
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