In the early 1880s, Loring A. Chase and Oliver Chapman bought much of the land that would become Winter Park. Over the next few years a railroad station and several hotels were built, and Winter Park became a popular vacation destination for wealthy northerners.

Rollins College was built in 1885 by the Congregational Church. The college acquired its current emphasis on the liberal arts under the direction of Hamilton Holt, president of Rollins from 1925 through 1949.

Winter Park was incorporated in 1887.