Why is Winter Garden, FL one of the fastest growing cities in the USA? Because Winter Garden’s proximity to Orlando and the theme parks has made it an ideal spot to live, work and visit. In the last 15 years, Winter Garden has exploded into one of the most family-oriented area’s in the state and the Winter Garden real estate market has exploded with it. From resort style communities, the ever so charming historic downtown, miles and miles of bike and fitness trails, sporting complexes, and farmer’s markets, there is always something to keep everyone in the family occupied. Winter Garden also has a thriving business community that over 2000 business call home. Small locally owned businesses line the streets of the historic downtown, and the over 1 million square foot Winter Garden Village shopping complex contains many of the national brands.