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Winter Garden & Oakland Park


A historic, sunny suburb just outside Orlando with easy access to everything it offers                          
Winter Garden is a sparsely populated suburb located just outside of Orlando, Florida. Nestled against the shores of Lake Apopka, this charming city has a historical, eclectic downtown filled with quaint restaurants, bright shops, and oozing with old-world Florida charm. Just a quick 20-minute drive away is the exciting theme parks of Orlando including Disney World and Orlando Universal Studios. Winter garden not only has an attractive downtown but also plenty of green outdoor space. Filled with playgrounds, parks, and a lovely bike trail, residents can easily enjoy the sunny Florida weather. Winter Garden is filled with plenty of luxurious, new home construction and includes beautiful styles of architecture like Mediterranean and classical revival. Homes are large and well spread out, and largely owned by residents creating a sparsely populated suburban feel.
Life in Winter Garden buzzes around downtown Plant Street, where art, music, shopping, and dining are always hopping. Residents can enjoy outdoor time in the city’s collection of parks and biking trails, or soak up the history of downtown Winter Garden.

What to Love

  • Historical downtown with vibrant shops and restaurants
  • Modern, new luxurious homes
  • Peaceful green spaces, such as playgrounds and bike trails
  • Easy access to Orlando and all it has to offer

Local Lifestyle

The local lifestyle in Winter Garden is classic, historical Florida. As a town built on the citrus boom and incoming railways, Winter Garden is quaint, classic, and enjoys a strong sense of community. Residents of Winter Garden enjoy community events, a vibrant downtown, and gorgeous, luxurious Florida homes.

Dining, Entertainment & Shopping

Downtown is centered around life on Plant Street. One of the star attractions is the Crooked Can Brewery, which offers delicious, local craft beers inside the Plant Street Market. Visitors can enjoy food from local vendors in the market alongside hand-crafted, unique beer offerings. Pilars is a 1930s deco bar specializing in mixology, martinis, and live music for a classic evening on the town. 
For dinner, Bella Italia Ristorante serves authentic Italian cuisine in an upscale dining room that transports visitors to Italy. Garden Theatre is a classical, historic theater hosting plays, musicals, concerts, and movies. The original theater was built as a single-screen cinema to show the first talking motion pictures in Florida. Today, residents can enjoy a taste of history by enjoying a modern play or musical in the theater.

Things to Do

Residents in Winter Garden have plenty of outdoor space to explore. The West Orange Trail is a well-paved, 22-mile long multi-use trail that spans from Killarney through Winter Garden to Apopka Station. Bike enthusiasts will love the well-paved trail, complete with playgrounds, parks, and facilities that wind through the Florida scenery. The trail is lined with classic Florida foliage, including weeping trees that drape over the path, providing shade and a beautiful Florida ambiance. After a long ride, cyclists will need to refuel and the Winter Garden Farmers Market has all one could need. Serving up fresh, local produce as well as carefully crafted snacks and drinks, the year-round market is a staple for the Winter Garden community.
The Winter Garden Heritage Foundation operates two museums in Winter Garden that supply residents with an extensive look at Winter Garden history. Photographs, memorabilia, and Native American artifacts create an extensive picture of the historical Winter Garden.
Nearby in Orlando, Disney World tempts residents with endless excitement, classic treats, rides, games, and more. Disney World is one of the top-rated amusement parks in the world and features an immersive experience like nowhere else. Winter Garden residents are able to enjoy a peaceful, quiet small town life with easy access to the amusement parks of Orlando.


Winter Garden is served by Orange County Public Schools and also has plenty of private and charter options. 

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