Many settlers moved into Ocoee when the Florida Midland Railroad reached completion in the 1880s. Larger areas were cleared for living space, and the market grew larger with more extravagant housing options. Crops like corn and sweet potatoes were quickly abandoned. New citrus and vegetables came from the winter market up north.
Ocoee’s first school was also established in 1880. The original three-sided hut was replaced by a two-story wooden school building. Eventually in the 1920s, this building was replaced by a brick school to house the town’s growing population.
One of the most famous names to come out of Ocoee was William Blakely. Blakely was the principal and teacher at Ocoee’s school and he also served as Postmaster and Justice of the Peace. A room in his home was devoted to the community as a library. In all, he spent more than half a century making Ocoee a better place to live.
As the Orlando Metropolitan Area began to expand, so did Ocoee’s population. In 1959, State Road 50 eventually connected Ocoee to Orlando. The new accessibility brought more developers and affordable housing to the area. The Ocoee-Orlando connection was secured after State Road 408 was completed. That road also connects to the University of Central Florida.