Windermere

Windermere Real Estate

Learn more about real estate market trends, lifestyle and recreation options, in Windermere.

Located about 15 miles southwest of Downtown Orlando, Windermere is one of the most highly sought after addresses in Florida. It is a small upscale family-friendly community and home to numerous professional athletes, celebrities, CEOs, and other executives nestled between Lake Butler and Lake Down. There are numerous gated golf course and lakefront communities with home prices ranging from the high $300,000 to $68,000,000. Downtown Windermere is only about 10 miles from Walt Disney World Resorts, 5.5 miles from Universal Orlando Resort, 10 miles from Sea World Orlando, and 20 miles from Orlando International Airport (MCO).

Windermere Popular Searches

Windermere Neighborhoods

$975,000

Median Listing Price

$327

Median Listing Home Price/SqFt

3,057

Population

Homes for Sale in Windermere

Learn the value of your home

Get New Property Alerts to your Email

Create your own Listing Manager Account

Quick Facts

Popular Neighborhoods in Windermere:	Orlando, Kissimmee, Winter Garden
Zip Codes in Windermere:	34786
Schools in Windermere:	Orange County Public Schools

Data derived from Realtor.com

Windermere FL Real Estate Market Report

Newest Homes for Sale in Windermere FL

View the newest homes for sale in Windermere listed in the last week.

Welcome to 6799 Helmsley Circle, a stunning 4-bedroom, 3.5-bathroom home in the charming Preston Square community of Windermere. This spacious 2,876 sq. ft. residence offers an extra-large upstairs bonus room, a den with French doors, a downstairs guest suite, and a screened-in porch overlooking a private greenbelt—providing the perfect blend of luxury and comfort. No rear neighbors! As you arrive, the beautifully landscaped front yard and inviting front porch set the stage for the peaceful lifestyle within. Step inside to an open-concept living area that seamlessly connects to the kitchen, featuring granite countertops, 42-inch cabinets, stainless steel appliances, and ample storage—ideal for both everyday living and entertaining. Upstairs, you'll find the master suite, a versatile bonus room, a laundry room, and two additional bedrooms. Situated in a prime location near Disney Theme Parks, this home is just minutes from Westside Shoppes, Lakeside Village Center (featuring Regions Bank, McDonald's, Rocca’s, Publix, Boteco do Manolo, Manzzo, Kingdom Sushi, and more), and Windermere Preparatory School. Zoned for some of the most sought-after public schools in the district. Don’t miss this opportunity—reach out today to make this dream home yours!

$799,000 Active

6799 Helmsley Circle Windermere, Florida

4 Beds 4 Baths 2,876 SqFt 0.13 Acres

$3,150,000 Active

5243 W Lake Butler Road Windermere, Florida

3 Beds 3 Baths 3,255 SqFt 0.56 Acres

Paradise Meets Location! Stunning Bungalow in Windermere Trails! Discover the perfect blend of luxury, location, and outdoor paradise in this meticulously maintained bungalow, sitting on the BEST CORNER LOT in Windermere Trails. From the moment you step inside, you'll be captivated by the professionally designed outdoor area, featuring a PRIVATE HEATED SALTWATER POOL with LED lighting and a cascading waterfall, a summer kitchen, artificial grass, and a fenced backyard—all crafted for the ultimate outdoor experience. And the magic doesn’t stop there! Every evening, enjoy a breathtaking view of DISNEY’S FIREWORKS right from your home, making every night feel like a celebration. Boasting 2,393 SqFt of living space, this bright and airy home offers 4 bedrooms, 3.5 bathrooms, and an attached 2-car garage. One of the home’s most unique features is the COMPLETE IN-LAW SUITE APARTMENT above the garage—ideal for guests, extended family, or even as an income-producing rental. This suite includes a living room, kitchen space, a private bedroom with a walk-in closet, and a full bathroom. Inside the main home, the gourmet kitchen is a chef’s dream, featuring stainless steel appliances, solid wood cabinetry, granite countertops, a walk-in pantry, and a kitchen island with eating space. The microwave and dishwasher were updated just last month. The open floor plan seamlessly connects the formal living room, dining area, and family/TV room, all leading to your private patio oasis. Enjoy wood flooring throughout the home, with ceramic tile in wet areas, combining elegance and durability. Step outside and fall in love with the brick-paved patio, PRIVATE HEATED SALTWATER POOL, cascading waterfall, summer kitchen, and lush tropical landscaping—a perfect setting for unforgettable gatherings. Upstairs, you will find three additional bedrooms, a dedicated office space, and a spacious laundry room with custom cabinetry and a utility sink. The Master Suite is a true retreat, featuring a tray ceiling, an oversized, redesigned walk-in closet, a private bathroom with dual vanity and standing shower, and a private balcony with breathtaking pond and sunset views. Nestled in a top-rated A+ school district, this friendly community is just minutes from Lakeside Village Plaza, Publix, fine dining, shopping, and top entertainment options. Enjoy community amenities such as a pool with water views, a dog park, a playground, and scenic walking trails. Freshly painted inside and out less than two years ago, meticulously maintained, and move-in ready. Please note: TVs, TV mounts, curtain rods, curtains, the chandelier in Bedroom #2, as well as the refrigerator and freezer in the garage, do not convey. Don’t miss this rare opportunity! Schedule your private showing today. Video tour available.

$720,000 Active

8498 Powder Ridge Trail Windermere, Florida

4 Beds 4 Baths 2,393 SqFt 0.18 Acres

Recently Sold Properties in Windermere

View the most recent Sold Homes in Windermere below.

No properties found

Virtual Showings & Open Houses in Windermere

Did you know the hottest homes for sale in Orlando often sell within days of being listed? Don't miss out! Set up your own custom property alert so you can be notified of the newest homes as they hit the market! Simply click the button below and choose the qualities that you want most in a home and save your search to start getting alerts today!

Join Deal Alert

As a local Orlando Real Estate Agent, I also have access to homes before they hit the market and can show you more homes and information that is only accessible in the MLS. If you would like to set up a time to go over your real estate needs, please free to contact me at your convenience. There is no obligation and or pressure... I hope to hear from you!