Winter Park, Florida, a charming city in Orange County, was established in the late 19th century as a meticulously planned resort community for wealthy northerners. Its significant development truly began in 1881 when visionaries Loring Chase and Oliver E. Chapman acquired land and strategically laid out the town, promoting it as an ideal winter escape, following earlier European settlement in 1858. A pivotal moment occurred in 1885 with the founding of Rollins College, Florida's first four-year college, which remains a cornerstone of the city's culture and prestige. Officially incorporated in 1887, Winter Park quickly grew, featuring luxury amenities like the Seminole Hotel. Today, its vibrant Park Avenue remains a central hub, home to civic buildings, museums, and the historic Rollins College, reflecting its enduring appeal and planned origins.