From this site via WFTV:
1. Settlers began arriving in the Winter Garden area in the 1850s. Attracted by the fertile muck land that bordered Lake Apopka, settlers engaged in citrus and vegetable farming, living in small settlements situated along the lake’s south shore.
2. By the end of the 19th century, Winter Garden’s business district had grown up alongside the two railroad lines that ran through the city.
3. Winter Garden was established in 1903 and incorporated as a city in 1908.
4. By 1920, there were more than 1,000 residents, and the city had quickly become the center of commerce and agriculture in West Orange County.
5. The Edgewater Hotel opened in 1927 as Lake Apopka’s emergence as “the large-mouth bass capital” attracted tourists.
6. Early residents either owned or worked in the groves, and as the citrus industry grew, the commercial district continued to expand.
7. By the turn of the century, a small commercial district had emerged along Plant Street and residential neighborhoods began to appear.
8. The historic fabric of Winter Garden remains largely intact. The historic buildings in Winter Garden date between 1915 and 1940.