Oakland is a town in Orange County, Florida, United States. The population was 3,516 at the 2020 Census, representing a growth of 38.5% over the population of 2,538 recorded during the 2010 census. It is part of the Orlando–Kissimmee Metropolitan Statistical Area.
Historic Town Hall constructed in 1912
Winter Garden is a city in western Orange County, Florida, United States. Located 14 miles (23 km) west of Downtown Orlando, it is part of the Orlando metropolitan area. The population was 46,964 as of the 2020 census.
Downtown Winter Garden on the West Orange Trail, with Plant Street
A photograph of downtown Winter Garden taken from Plant Street, looking east. Taken before or during 1909.
Topography of Winter Garden
The West Orange Trail