Winter Park is a suburban city in Orange County, Florida, United States. The population was 24,090 at the 2000 census. According to the U.S. Census Bureau's 2006 estimates, the city had a population of 28,083. The 2010 census count was 27,852, suggesting a small decline in 2007-2010. It is part of the Orlando–Kissimmee Metropolitan Statistical Area. The city is home to Rollins College, Full Sail University and the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass. Winter Park features open park space, residential areas, and a street-side shopping district along Park Avenue.

Winter Park was founded as a resort community mainly by northern business magnates in the late 19th and early 20th centuries. It is recognized as the first centrally planned community in Florida; 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. Many structures are more than 100 years old. The scenic Olde Winter Park area is punctuated by small, winding brick streets, and a canopy of old Southern Live Oak and Camphor trees, draped with Spanish Moss. The city draws thousands of visitors to annual festivals including the Bach Festival, the nationally ranked Sidewalk Art Festival, and the Winter Park Concours d'Elegance.