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Winter Park Florida was founded as a resort destination by wealthy New England industrialists before the turn of the 20th century. It is recognized as the first centrally planned community in Florida; its main street includes not only public civic buildings and retail, but also art galleries, a private liberal arts college, museums, a professional theater, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch.

Winter Park Florida is celebrated for a sense of place and history, uncommon to many parts of Central Florida. 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.