Winter Garden Homes for Sale

Listed below are homes for sale in Winter Garden, a city located in Orange County. These luxury Winter Garden real estate listings are updated every 15 minutes from the MLS. 

For additional information on any of these luxury Winter Garden homes for sale, just click the "Request More Information button located on the detail page of each listing. And to view any of the luxury Winter Garden listings you are interested in, click the "Schedule a Showing" button displayed on every property detail page to contact us and setup a time. In addition, we can provide you with disclosures, past sales history, dates and prices of properties recently sold nearby, and more.

And, if you haven't already, be sure to register for a free account to automatically receive email alerts whenever new Winter Garden listings come on the market that match your specific criteria and save your favorite properties for quick and easy access.

Read more about Winter Garden!

Winter Garden July 14, 2024
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615 Properties
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Winter Garden 

A great place for families, Winter Garden embodies a wealth of history, as well as natural assets. From its Historic Downtown to the award-winning West Orange Trail, Winter Garden has many recreational amenities, events, and historical assets that guarantee its residents will always have a new nook or cranny to explore. If you’re looking to settle in a place with history, nature, and vibrancy hidden in every corner, consider a home in Winter Garden. 


Winter Garden is home to farmer’s markets, a historic downtown, and countless trails. Twelve years and counting, the Winter Garden Farmer’s Market provides residents with the opportunity to pick up fresh herbs, produce, plants and flowers, baked goods, and more. The Historic Downtown, which is listed on the National Registry of Historic Places, gives residents the chance to explore the rich history of Winter Garden. Settled in the 1850s, most buildings in Winter Garden are dated between 1915 and 1940, and its historic fabric remains largely intact. For those looking to spend their weekend getting back into nature, Winter Garden offers plenty of opportunities to explore its beautiful landscape. Head to West Orange Trail, a 22.26-mile trail that winds its way along Lake Apopka. The trail is slated to be part of the 250-mile Coast to Coast connector trail that will connect the Gulf of Mexico to the Atlantic Ocean. 

Along with its extensive historical and recreational opportunities, Winter Garden hosts many events that bring together its community. For car enthusiasts, Winter Garden holds a quarterly car show. Each Friday, residents can enjoy live music on the Plaza in Winter Garden. Each summer, stroll the brick-lined streets for the Summer Sidewalk Sale, and each winter, kick off the holiday season with the Merry Winter Garden Light Show.  


Winter Garden, located in Orange County, is home to multiple A-rated schools that have an average student to teacher ratio of 16 to one. To learn more about Winter Garden’s educational institutions, visit the Orange County Public Schools website.  

Foodie Central

Winter Garden is a known hotspot for local foodies, mostly thanks to the iconic Plant Street Market, a community food hub and market. Grab a beer at Crooked Can, a local craft brewery with award-winning brewmasters. If you’re looking to grab a bite to eat, Plant Street Market offers a variety of cuisine to satisfy even the pickiest of eaters. Grab a spicy tuna roll at Jōdo sushi, create your dream mac and cheese at MAC’d Out, or visit The Local Butcher for fresh-cut roasts, steaks, and more.  

Winter Garden prides itself on being a great place for families. For those looking for an endless amount of events, culture, history, nature, food, and more, consider a home in Winter Garden.

For a stress-free real estate experience, contact Hector Leon of Orlando Florida Realty.

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