The Winter Park area’s first human residents were migrant Muscogee people who had earlier intermingled with the Choctaw and other indigenous people. In a process of ethnogenesis, the Native Americans formed a new culture which they called “Seminole”, a derivative of the Mvskoke’ (a Creek language) word simano-li, an adaptation of the Spanish cimarrón which means “wild” (in their case, “wild men”), or “runaway” [men]. The site was first inhabited by Europeans in 1858, when David Mizell Jr. bought an 8-acre (32,000 m2) homestead between Lakes Virginia, Mizell, and Berry. A settlement, called Lake View by the inhabitants, grew up around Mizell’s plot. It got a post office and a new name-Osceola-in 1870.

The area did not develop rapidly until 1880, when a South Florida Railroad track connecting Orlando and Sanford was laid a few miles west of Osceola. Shortly afterwards, Loring Chase came to Orange County from Chicago to recuperate from a lung disease. In his travels, he discovered the pretty group of lakes just east of the railbed. He enlisted a wealthy New Englander, Oliver E. Chapman, and they assembled a very large tract of land for $13,000 on July 4, 1881. They planned the town of Winter Park on this piece of land. Over the next four years they plotted the town, opened streets, built a town hall and a store, planted orange trees, and required all buildings to meet stylistic and architectural standards. Winter Park was a heavily planned city, something that is still evident in its streets’ grindlike organization. The town was then promoted heavily, especially to snow birds in the north looking for a place to hibernate in the winter. During this founding time, the Winter Park Post Office opened, and the railroad constructed a depot, connected to Osceola by a dirt road.

In 1885, a group of businessmen started the Winter Park Company and incorporated it with the Florida Legislature; Chase and Chapman sold the town to the new company. In a land bubble characteristic of Florida history, land prices soared from less than $2 per acre to over $200, with at least one sale recorded at $300 per acre. This land bubble concept would never go away, with towns and counties directly surrounding the area with exponentially cheaper land prices.