Winter Park is a city in Orange County, Florida, United States. The population was 30,825 according to the 2019 census population estimate. It is part of the Orlando–Kissimmee–Sanford, Florida Metropolitan Statistical Area.
Winter Park was founded as a resort community by northern business magnates in the late 19th and early 20th centuries (Founded on July 4, 1881 - Tales of Winter Park). Its main street, called Park Avenue, is located in the middle of town. It includes civic buildings, retail, art galleries, a private liberal arts college (Rollins College), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch. Park Ave marks the center of town, but it also marks the dividing line between the upper class white neighborhoods and the lower class black neighborhoods that make up the town. This line is further accentuated by the railroad track that runs parallel to the avenue. As the center of Winter Park’s social scene and culture, Park Ave walks the fine line of cultural center and tangible icon of gentrification.
The Winter Park area's first human residents were migrant Muscogee people who had earlier intermingled with the Choctaw and other indigenous people.