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, upon which they planned the town of Winter Park.
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.
They promoted it heavily.
During this 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.

In 1885, the Congregational Assembly of Florida started Rollins College, the state's first four-year college.
The following year 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.
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, upon which they planned the town of Winter Park. 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. They promoted it heavily. During this 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.
In 1885, the Congregational Assembly of Florida started Rollins College, the state's first four-year college. The following year 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.
Winter Park, Florida