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 afterward, Loring Chase came to Orange County from Chicago to recuperate from 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’ grind-like organization. The town was then promoted heavily, especially to snowbirds 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.

In 1885, the Congregational Assembly of Florida started Rollins College, the state’s first four-year college. Rollins College today remains one of the hallmarks of Winter Park. However, Rollins College further highlights the racial disparities within the town. It is the second most expensive college in the state with a tuition of $64,972 per year.

Rollins is a relatively good, small liberal arts school with a total student body of just over 2,000 students. However, the high price makes the overall rating of the school more into the middle of the pack of colleges around the country. The school’s business school is the Crummer School of Business. where students can earn an MBA, is a premier Business School. It is the number one business school in Florida. Rollins has been and will always be an integral part of Winter Park’s history and culture. However, the average student at Rollins is on scholarship.

Many in-state students are less interested in attending the school based on its high tuition. Back in 1886, the Seminole Hotel on Lake Osceola opened. This was a resort complete with the luxuries of the day: gas lights, steam heating, a string orchestra, a formal dining room, a bowling alley, and long-covered porches.[citation needed]Today, this street is a cul de sac called Kiwi Circle that is part of one of the nicest neighborhoods in the town.