Winter Park is a suburban city in Orange County, Florida, United States. The population was 27,852 at the 2010 United States Census. 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. Its main street includes civic buildings, retail, art galleries, a private liberal arts college, museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch.