Winter Garden Florida

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Winter Garden Florida Homes and Community.

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Winter Garden grew from small settlements adjacent to Lake Apopka Florida. Most settlers who arrived at Winter Garden in the nineteenth century were farmers who grew citrus and vegetables crops. Tavares & Gulf Rail Company and The Atlantic Coast Line railroad lines ran thru Winter Garden which was a key component of the Winter Garden economy that exported produce and freight and imported people from all over the State. Winter Garden was a destination visited by the likes of Famous celebrities, such as Humphrey Bogart and Clark Gable. Winter Garden continued to grow quickly was officially established in 1903 and incorporated as a city in 1908. Most of the commercial building on Plant & Main Street were wooden built, but after several fires rebuilt with brick, which gives Winter Garden its old town country looks today.

By 1920 Winter Garden had grown exponentially and became the center of commerce of West Orange County. Most of the early residents owned or worked for the agricultural companies and its many groves. Due to urban and industrial development Lake Apopka became so polluted that eventually many residents and businesses moved away. But Winter Garden prevailed the establishment of attraction like Disney and West Orange Trail attracted a new blood to their historic old charm buildings. Its residents and community leaders rallied and brought back Winter Garden commercial district which was listed on the National Register of Historic Places in 1996.

Today, Winter Garden’s Historic District serves as a successful example of historic preservation.  Infill development, redevelopment, repurposed buildings, preservation, housing and businesses all converge to create a thriving downtown that draws people from around the world.

Winter Garden Florida THINGS to DO!

Amazing adventures ready for you and your family.

Downtown Winter Garden Farmers Market

The market offers live events, fairs, festivals, and lots of other family-friendly entertainment. Located in the downtown area, it’s open every Saturday from 9 AM until 2 PM. Winter Garden Farmer’s Market would be a great place to check out. Winter Garden and Florida in general are some of the country’s most abundant fruit and vegetable producers. For those looking to have access to all those seasonal fruits and vegetables in one location the farmers market is the place.


Located on West Plant Street in downtown Winter Garden, Crooked Can Brewing Company is known for its relaxed environment, helpful staff, and great foods that includes burgers, sushi, wings, and even a few vegan options. They offer a variety of beers that come in an array of flavor profiles, so try a sampler to see what you like before ordering a pint or two. Nothing tops off a long day on your feet in the sweltering Florida sun better than a cold brew, and when it’s brewed locally and with natural ingredients, so much the better.


The museum is located on South Boyd Street and is a particularly relevant destination for history, railroad, and transportation buffs. The items on display include equipment, photographs, first-hand accounts, and other unique bits of local history pertaining to the area’s development and railroads. The Central Florida Railroad Museum in Winter Garden is housed in the historic depot of a now-defunct railway and is open every day except holidays from 1 until 5 PM.



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