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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11728 Water Run Aly, Windermere, Florida 34786

Residential Lease For Rent

HEXAGON
Fabulous end-unit townhome available for rent, loaded with upgrades. Exceptional location—walk to new restaurants, shops, and Publix.
$2,670
3Bedroom(s)
3Bathroom(s)
1,712Sqft

8205 Serenity Spring Dr #502, Windermere, Florida 34786

Residential Lease For Rent

SUNNY 365 REALTY GROUP
Beautiful 4 bedrooms 2.5 baths townhome in resort style gated community. The entire first floor has an open floor plan, granite counters and stainless steel appliances. Upstairs has 3 bedrooms with walking closets and 1 master bedroom downstairs, 2 car garage. The community offers a community pool, fitness center, large pond with walking trails around the water.
$2,650
4Bedroom(s)
3Bathroom(s)
2,067Sqft

11642 Water Run Aly, Windermere, Florida 34786

Residential Lease For Rent

VS INTERNATIONAL PROPERTIES
3 bedroom 2 bathroom townhouse.Ashlin Park is a peaceful community located in the beautiful town of Windermere. This neighborhood offers a community pool and clubhouse for your comfort and convenience. Ashlin Park is an ideal location due to its proximity to the Lakeside Shopping Center, many highly rated K-12 schools and Walt Disney World. 1 Year Lease HOA Approval might be required.
$2,650
3Bedroom(s)
3Bathroom(s)
1,624Sqft

12958 Vennetta Way, Windermere, Florida 34786

Residential Lease For Rent

THE LISTING REAL ESTATE MANAGEMENT
Absolutely stunning 3BD/2.5BTH 1,644 sqft end unit townhome in Berkshire Park subdivision of Windermere! Prime location, centrally located, corner lot. Near Disney attractions and to the Winter Garden Village for shopping and dining. Property features ceramic tile on main floor, SS appliances, granite counter tops, just to name a few of the many upgrades.
$2,600
3Bedroom(s)
3Bathroom(s)
1,644Sqft

7332 Yoder Street, Windermere, Florida 34786

Residential Lease For Rent

FLORIDA CONNEXION PROPERTIES
Location, Location, Location. Gorgeous 3BR 2.5BA home move-in ready for new residents. No carpet throughout the bedrooms. stainless steel appliances, full of cabinets, and two pantries, 2 car garage. Deposit determined by credit score. Applicant to verify school. Renter insurance is required. Pest control is the occupant's responsibility.
$2,600
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,484Sqft

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.
$2,600
3Bedroom(s)
2Bathroom(s)
1,710Sqft

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.
$2,600
3Bedroom(s)
3Bathroom(s)
1,881Sqft

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.
$2,575
3Bedroom(s)
3Bathroom(s)
Garage Door OpenerParking(s)
1,852Sqft

14242 Desert Haven St #ge, Windermere, Florida 34786

Residential Lease For Rent

REAL BROKER, LLC
Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a comfortable, low-maintenance lifestyle just minutes from Disney—with clear views of the nightly fireworks from your own home. The interior features a functional two-story layout with all bedrooms located upstairs, providing separation between living and private spaces.
$2,550
3Bedroom(s)
3Bathroom(s)
1,534Sqft

13075 Calderdale Ave, Windermere, Florida 34786

Residential Lease For Rent

BELLA TRAE REALTY
This beautiful 3-bedroom townhome is available for rent! The kitchen features granite countertops and stainless steel appliances, making it both functional and stylish. The first floor includes a spacious family room, dining area, convenient half bathroom, and a laundry room with a full-size washer and dryer. Upstairs, the primary suite offers dual sinks and a walk-in shower.
$2,550
3Bedroom(s)
3Bathroom(s)
1,625Sqft

7231 Shadeview Aly, Windermere, Florida 34786

Residential Lease For Rent

SUNNY 365 REALTY GROUP
Beautiful 3 beds, 2.5 baths, 2 car garage townhome at Ashlin Park in the heart of Windermere. Must see all this community has to: Community Pool, Club House, Playground, Conservation areas, ponds, access to bike trail and just at walking distance from Restaurants and market places. Right next to the 535 road, one mile away from Publix and commercial development with many new restaurants.
$2,550
3Bedroom(s)
3Bathroom(s)
1,725Sqft

7621 Sutherton Ln, Windermere, Florida 34786

Residential Lease For Rent

MY REALTY GROUP, LLC.
One or more photo(s) has been virtually staged. Discover your new home at 7621 Suthertone Lane, nestled in the heart of Windermere’s charming Wickham Park community.
$2,500
3Bedroom(s)
3Bathroom(s)
1,520Sqft
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