Winter Garden Area Guide and Home Search A thriving city with a small-town feel.
Winter Garden continues to grow. What was once a sleepy agricultural town is now one of the most sought-after cities in Central Florida; a city that sits under giant shade trees and brings people from all walks of life together.
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Winter Garden at a Glance
As you drive down the brick streets of Downtown Winter Garden, you’ll immediately feel like you’ve been transported back in time. This charming downtown area features wide sidewalks and tree-lined streets, locally owned businesses and restaurants, an old-fashioned ice cream store, a library, a playground, and a splash pad. Downtown Winter Garden is surrounded by impressive waterfront real estate, new developments, luxury high rises, and historic neighborhoods. Families flock to Winter Garden for the gorgeous suburbs, highly rated schools, and the active community. Winter Garden is a place where generation after generation put down roots, build business and families. It’s also close to the theme parks, beaches, and vibrant art and culture scene of Downtown Orlando.
Winter Garden’s rich history dates back to 1903, and while the city has grown rapidly since then, you can still find pieces of Winter Garden’s story if you look closely throughout the city. Winter Garden started as farmland, producing vegetables and citrus among a few simple settlements. At the end of the 19th century, a railroad ran through the city, making it easier for the city to export its goods throughout the state. A fire ravaged the town in 1909 and burned down many of the buildings on Main Street and Plant Street. These buildings were rebuilt, and Winter Garden saw a surge of regrowth in the 60s. Now, it is a thriving city with a small-town feel.
Winter Garden continues to grow. What was once a sleepy agricultural town is now one of the most sought-after cities in Central Florida; a city that sits under giant shade trees and brings people from all walks of life together.
Things to Do in Winter Garden
Winter Garden Farmers Market
Every weekend, the heart of Downtown Winter Garden comes alive with local vendors and artisans, showcasing their goods at the award-winning Farmer’s Market. Local farmers sell fresh produce and small business owners sit under tents and sell everything from handmade jewelry and artwork to gourmet dog treats and elegant calligraphy services. The Farmer’s Market features local food trucks and live music, and is one of the best ways to support small businesses and connect with the community.
Visit the Local Brewery
The Crooked Can is Winter Garden’s very own brewery. Tucked under large shade trees in the heart of downtown, this modern brewery offers local craft beers and large indoor and outdoor sitting areas. A small grassy area is perfect for kids to run around in while parents enjoy live music and a cold brew. The Crooked Can doesn’t serve food, but you can order food from the neighboring restaurants and enjoy it inside or out on the picnic tables.
Shop The Plant Street Market
The Crooked Can is located at the far end of the Plant Street Market. This indoor shopping venue is home to a variety of locally-owned restaurants, ranging from sushi and sandwiches to smoothies and pizza. The Plant Street Market feels like a sophisticated flea market, but with gourmet food instead of antiques.
Play At A Local Park
Winter Garden has dozens of public parks, nature trails, and outdoor recreation areas. Tucker Ranch features a modern wooden playground, while Chapin Station is the “go-to” park for kids and families after school each afternoon. Winter Garden’s parks sit under large shade trees draped with Spanish moss and have wide sidewalks perfect for walking, running, and pushing strollers. There is a splash pad in Downtown Winter Garden that is popular in the summer, and a climbing playground right next to the library.
Ride Down the West Orange Trail
The West Orange Trail is a 22-mile paved walking path that weaves in and out of local neighborhoods and straight through the heart of Downtown. The trail winds through shady parts of the city, over bridges, around playgrounds, and into the most scenic parts of the area. On any given day you can find people walking, biking, running, skating, and pushing strollers down the trail. The trail is the heart of Winter Garden, allowing residents to get outside, stay connected, and stay active.
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Notable Communities & Neighborhoods in the Area
- Overlook At Hamlin
- Covington Chase
- Cypress Reserve
- Fullers Crossing
- John’s Lake Pointe
- Lakeview Preserve
- Overlook At Hamlin
- Summerport
- Summerlake
- Stoneybrook West
- Waterleigh
- Watermark