History of Park Avenue, Winter Park

1881: New Englanders Oliver Chapman and his friend Loring A. Chase purchase 600 acres bordering Lakes Maitland, Osceola, Virginia and Killarney for $13,000. They refer to their property as a “necklace” of lakes surrounding lush acreage. Their goal is to develop a residential community of winter homes for wealthy Northerners—a “planned community.” It is the very first one in Florida and they name the new town “Winter Park”. Designing around a central park and its main street, Park Avenue, they designate home sites, a hotel, churches, schools and parks and market their Florida enclave to northerners fleeing harsh winters. Soon the railroad pulls into Central Park with loads of affluent tourists who stroll down Park Avenue.

1888 – Corner of Park Avenue and New England

From the tourism boom of the 1890s to today Park Avenue has provided the citizens and visitors of Winter Park with an elegant place to stroll, dine, and shop.

*Text and images provided by the Winter Park Historical Association.