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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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 #304, Windermere, Florida 34786

Residential Lease For Rent

RE/MAX PRIME PROPERTIES
The perfect blend of comfort, convenience, and Central Florida lifestyle! This beautiful ground-floor residence offers effortless living with an open-concept floor plan that flows seamlessly from the kitchen to the living and dining areas—perfect for relaxing or entertaining.
$2,300
3Bedroom(s)
2Bathroom(s)
NoneParking(s)
1,455Sqft
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7708 Bexton Ln, Windermere, Florida 34786

Residential Lease For Rent

ALTIS REALTY
Beautiful 3 bedroom 2.5 bath townhome located in Windermere! The home features an open kitchen with stainless steel appliances and beautiful 42" cabinets . Just off the dining area step out to the cozy fenced in courtyard. Upstairs there is a large master bedroom with walk in closet. The master bath features dual sinks and tiled walk in shower.
$2,300
3Bedroom(s)
2Bathroom(s)
1,335Sqft
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8265 Maritime Flag St #101, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA REALTY INVESTMENTS
Move right in! This beautiful 3-bedroom, 2.5-bath corner-unit townhouse is available for immediate move-in and offers the perfect combination of space, comfort, and community living. Step inside to a bright, open-concept layout where the spacious kitchen flows seamlessly into the dining and living areas—ideal for entertaining guests or unwinding at the end of the day.
$2,250
3Bedroom(s)
3Bathroom(s)
1,644Sqft
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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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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.
$2,100
3Bedroom(s)
2Bathroom(s)
CommonParking(s)
1,442Sqft
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8168 Boat Hook Loop #107, Windermere, Florida 34786

Residential Lease For Rent

WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
A beautiful 3-bedroom ground-floor condo located conveniently opposite the clubhouse which has all the luxury amenities you could ask for. Inside, you'll be wowed by the size of the living space, which includes a large living room with a separate dining area, as well as a large kitchen with a breakfast bar, stone countertops, and newer stainless steel appliances.
$2,100
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,455Sqft
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11564 Mizzon Dr #104, Windermere, Florida 34786

Residential Lease For Rent

WATSON REALTY CORP
Spacious condominium in the heart of Windermere. This first floor 3 bedroom, 2 bath features a walk in kitchen, large dining-living combo area, dual entrance second bathroom, and screened in porch leading to the garden area. With a split floor plan, the primary bedroom features a private bath and large walk-in closet.
$2,100
3Bedroom(s)
2Bathroom(s)
1,332Sqft
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8264 Maritime Flag St #1419, Windermere, Florida 34786

Residential Lease For Rent

RED DOOR INVESTMENT GRP LLC
Beautiful Lakeside at Lakes of Windermere 2nd floor 2 bedroom condo with an open floor open, 42" cabinets, under cabinet lighting, breakfast bar and crown molding. Master bedroom has a large walk in closet and the master bath comes with a large vanity and walk in shower. All appliances including washer and dryer are included, along with water, sewer and valet trash.
$2,095
2Bedroom(s)
2Bathroom(s)
1,161Sqft
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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.
$2,000
3Bedroom(s)
2Bathroom(s)
GuestParking(s)
1,442Sqft
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8168 Boat Hook Loop #202, Windermere, Florida 34786

Residential Lease For Rent

HAMPTON & HAMPTON MGMT LEASING
2/2 Windermere condo walking distance to the pool with resort style amenities. Kitchen has granite counter tops, 42" cabinets. Main suite has huge walk-in closet and bath has decorative tile, lighted shower and double sinks. Community features pavilion on the lake, screened patios, barbecue area and fitness center. Valet trash included. HOA app fee per person-15 day approval process.
$1,775
2Bedroom(s)
2Bathroom(s)
1,161Sqft
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