Discover Downtown Winter Garden Florida Today!


There are multiple reasons why Winter Garden is a hot spot for those local and people who have recently relocated to the area.  If you do not feel like walking then you are only a golf cart drive away from local shops, restaurants, and the fun. It has a genuine small town feel with a great walkability factor. There are both new and old restaurants which are beautifully blended in a central location. It is located approximately 20 minutes outside of downtown Orlando and is connected to major highways and expressways.  You’ll discover tons of history and you’ll have multiple options when it comes to choosing a home. The styles range from mid-century, historic, Victorian, new construction, single family homes, and luxury townhomes.

Let’s take a look at some specific attractions and things to discover in Downtown Winter Garden –

  • Winter Garden Food Tours – A Winter Garden food tour is where people gather to be a part of a tasting experience. It provides an opportunity for you to sample food items from multiple restaurants and bakeries.  It’s also a place to meet people and share food experiences with like-minded folks. Calling all foodies!

  • Market To Table –  Original to Downtown Winter Garden and located in the heart of the historic area, Market To Table creates modern American cuisine with classical influences. This is definitely an experience to have while you are in Winter Garden and if you are local then you’ll want to visit it more than once!

  • The Historic Edgewood Hotel – This is THE place to stay in Downtown Winter Garden or to send family and/or friends who may be visiting you. It is a historic B&B from the 1920’s and each one of the rooms is uniquely decorated and furnished. You’ll also find 3 places to choose for dining, an old-fashioned ice cream store, AND an old-style barbershop!! It really is a fun place to stay.

  • Plant Street Market – The new-but-vintage-looking Plant St. Market is a local indoor artisan market made up of 17 locally owned and independent businesses, creating an experience as unique as the diversity, variety and artisan specialties offered at each unit. Open 7 days a week, you’ll find something for everyone here including quality craft beer from award-winning Crooked Can Brewing Company. There’s also live entertainment and a pet-friendly patio. Definitely, a place to enjoy a day.

  • Crooked Can Brewery – This is definitely a draw for locals, tourists and people visiting locals. 🙂 The response is that once you go you’ll want to return.

  • Winter Garden Heritage Museum – A great place to gain a historical perspective on the area. The museum is located right on Main Street and is open 7 days a week.

  • Saturday Farmers Market – Open all year round every Saturday from 9:00 AM to 2:00 PM. This is a very popular destination in the downtown Winter Garden area as it should be. One can stock up on fresh produce, shop LOCAL vendors, and enjoy a day of family fun!! There’s also live music to enjoy!

  • Garden Theatre – Located in the heart of historic downtown Winter Garden on Plant Street in a repurposed vintage movie theatre that reopened in 2008, showcases atmospheric theatre in a Mediterranean Revival-style venue. The Garden Theatre hosts live plays, concerts, movies, and more to the residents of and visitors to the city of Winter Garden and the surrounding Orlando area.

  • West Orange Trail – A world-class rail trail through urban and suburban sections of Orange County. Popular for all types of biking, in-line skating, running and walking. “Outposts” and “Stations” along the trail provide parking and facilities, with the Stations more fully-featured. The trail runs from the Killarney Station trailhead on SR50 west of Oakland, through Winter Garden and to Apopka, ending at Welch Road. The trail also comprises a portion of the Florida Coast-to-Coast Trail.

If you wish to explore this area in person and are from out of town, please contact me. Let’s get you acquainted with one of the best places to live and feel free to search for homes in this area on my website. Search Winter Garden Homes.

Follow me on Instagram if you’re interested in learning more about Central Florida, home styles, and interior design.