Winter Garden is a charming town that has been gaining increasing prominence on the Central Florida map. It maintains a small-town atmosphere typical of Florida’s interior while offering all the infrastructure needed for full-time living or as a second home. The city, rich in history and over a century old, has as its main highlight its commercial center, known as the Winter Garden Historic District. This area, with its preserved architecture, is listed on the National Register of Historic Places. Strolling through its downtown, visitors can enjoy local architecture, unique shops, cafes, restaurants, museums, and even a well-known craft brewery worth visiting — which we’ll discuss later in this article.
Located in the same county as Orlando (Orange County) and just 20 minutes from downtown Orlando, Winter Garden combines convenience with quality of life. Its easy access to theme parks and major attractions of Orlando, along with a family-friendly atmosphere, good schools, safety, and a peaceful residential vibe, makes it one of the top choices for living or investing near Orlando.
Quality of life by the lake!
Winter Garden is located on the shores of Lake Apopka, the third largest in Florida. The entire central region of Florida is known for its chains of lakes, offering a wide range of benefits associated with living by the water, such as water sports, fishing, boating, in addition to the beautiful landscapes and rich fauna and flora of the surroundings, which provide a deep connection with the local nature. Discover the main lakeside cities to live in Central Florida
The Big Fire! .. And Other Interesting Facts
To fully experience Winter Garden, whether you are visiting it or considering a real estate investment, it is essential to know some historical facts and curiosities that have shaped the city over time:
- It all started in 1850 with orange plantations: The first settlers settled on the fertile lands around Lake Apopka, planting mainly oranges. Hence the origin of the name “Orange County” for the county where Winter Garden is located.
- The Expansion of the Rails: In the late 19th century, Winter Garden’s commercial district began to develop along the two railroad lines that crossed the city.
- The Great Fire and the new brick buildings: Two major fires (1909 and 1912) destroyed the wooden buildings and packing houses along Plant and Main streets. This tragedy led to the reconstruction of the buildings in brick, making the downtown more resistant and durable. That’s why today the predominant architecture in the city’s historic downtown is exposed brick, which adds a special charm!
- The decline (1960s): In the 1960s, the aggressive development of Winter Garden slowed significantly. Lake Apopka suffered from severe pollution, impacting the orange groves. In addition, the construction of major highways in the area diverted commerce from the city center.
- The resurgence: Despite these challenges, Winter Garden’s architectural heritage has remained intact. The creation of the West Orange Trail, a 22-mile recreational trail built on an old railroad line, played a vital role in the rebirth of the city’s historic downtown. This trail attracts visitors who explore the local shops, cafes, and restaurants, contributing significantly to the revitalization of the economy and promoting tourism. Below, we will discuss in more detail the importance of the West Orange Trail and its impact on the community.
- Historic Registration: In 1996, the historic center was included in the National Register of Historic Places thanks to the community effort, transforming it into a vibrant example of revitalization and architectural preservation.
These are just a few historical facts and curiosities that we believe are important to share in this article. To learn more about the history of the city and the region, click here.
Things to do in Winter Garden, Florida
The city of Winter Garden, being located in the central region of Florida and close to downtown Orlando, offers a list of incredible things to do. Below we list some interesting tours and attractions:
Walking through the Historic Center (Winter Garden Historic District)
The main attraction is the historic center, located on the city’s main avenue, Plant Street. It is along this street that you will find the main shops, restaurants, sweet shops, cafes — with emphasis on the popular Axum Coffee — and the well-known Plant Street Market, which is next to the renowned craft brewery, the subject of the next topic.
As mentioned, downtown Winter Garden is listed on the National Register of Historic Places. With its exposed brick buildings and preserved architecture, the area offers unparalleled charm. The choice of brick came about after two fires destroyed the old wooden buildings, marking a new era in the city’s landscape.
Crooked Can Brewing Company
If you’re looking for things to do in Winter Garden, don’t forget to visit the Crooked Can Brewing Company!
This is a traditional brewery in Winter Garden that’s great for the whole family, even for those who don’t like beer. That’s because the Crooked Can Brewing Company is much more than just a brewery that offers craft beer; it’s also a local food hub. It’s attached to the Plant Street Market, which offers a variety of food stands for all tastes: pizza, sushi, burgers, pork, shoulder, and even vegan dishes. Plus, the atmosphere is really nice, relaxed, and fun! If the weather is good, try to get a table outside and enjoy the day with great drinks and local food at fair prices tailored to the American public.
Winter Garden Village
A little far from the historic center of Winter Garden is the Winter Garden Village, an open-air shopping mall with more than 80 stores, including: Marshalls, Super Target, Carters, Oshcochi, Best Buy, Forever 21, Ross, among other famous stores that are favorites of Brazilians. The great advantage of shopping at the Winter Garden Village is that it is not so crowded with people everywhere and the place is very beautiful and charming. It is even worth walking and strolling around there. Not to mention the very good restaurants that the Village offers. The place also has ample parking. Learn more on the official website
West Orange Trail
The West Orange Trail is a 35 km trail built, for the most part, on train tracks from the old railroad line in the region. It starts in downtown Oakland and goes all the way to Apopka, passing through downtown Winter Garden. The trail is paved and designed for cycling, walking and other outdoor sports. There are several playgrounds for children along the trail. The bike path is very well marked and maintained and passes through bucolic places. It is possible to rent bikes in the historic center of Winter Garden, where the West Orange Trail passes. A recommended place is the Wheel Works – Bike Rental Station.
Taking the trail is a very pleasant ride, rich in history and culture, as it passes through towns and urban centers characteristic of this region of Florida, as well as forests and old orange plantations, which recall the roots of the original economic activity of Orange County.
The West Orange Trail project is still under development. When completed, the trail will be a multi-use greenway, with 36 miles (58 km) of paved roads with an average width of 4.5 meters.
Lake Apopka: Leisure and connection with nature
As mentioned, the community is located on the outskirts of Lake Apopka, which is the third largest lake in Florida and where nature is very rich. Enjoy the wildlife and admire the variety of birds. Watch out for alligators! They are there in abundance. Take advantage of relaxing on the shores of the lake and all the benefits that life by the water can offer, with water sports and leisure activities, such as fishing, water games, boat rides, among others.
Farmer’s Market in Winter Garden – Florida
The Farmer’s Market in Winter Garden is a small market that takes place only on Saturday mornings in a square near Plant Street. The market brings together several stalls with the most varied types of food as well as souvenirs, accessories, jewelry and local products. Interestingly, in this same square where the market takes place, there are those water jets that come out of the ground (fountains) where children can play on hot days. Confirm the opening hours and learn more about the Farmer’s Market on the official website
These are just a few things to do in Winter Garden, a fantastic city that is ideal for a family outing. This is a great tip for those who want to take a break from the marathon of parks.
Ideal for living and also a great city for investing
Winter Garden is currently one of the most attractive cities for real estate investment in the Greater Orlando region. Because it has not yet been widely explored like the more recognized centers, such as Miami and more central neighborhoods of Orlando, the real estate market in Winter Garden maintains more affordable prices with a high potential for appreciation.Its strategic location, surrounded by lakes such as Lake Apopka, adds value to properties, as waterfront land is scarce and highly sought-after, resulting in good prospects for financial returns.
A key factor driving this appreciation potential is the development of Horizon West, a nearby master-planned community. The area is projected to house approximately 90,000 residents in a mixed-use development that includes a downtown area with restaurants, shops, cafes and entertainment centers. Horizon West is being developed in six greenbelt villages, each ranging from 400 to 1,200 hectares and consisting of two to four neighborhoods centered around community schools and parks. The focus on trails, bike paths and community spaces enhances the community appeal of the project.
A large portion of Horizon West has already been completed, offering residents a modern and planned infrastructure, while full delivery of the project is expected to take up to 20 years.
About CAP International
If you are interested in buying a property in Winter Garden or another region of Central Florida, contact me and chat with me on WhatsApp: click here to access my WhatsApp (Carlos Barros).
CAP International is a global real estate agency specializing in Florida and has a team of professionals to guide you throughout the entire purchasing process. Our consultancy goes far beyond brokering a property abroad. We want to be your partner in the United States.