Winter Park

Population29,795 (2020)
Incorporated1925

Winter Park, Florida’s history is a fascinating tale of transformation from a small settlement to a thriving community. Originally named Lakeview in 1858, the area was later renamed Osceola. It wasn’t until the late 19th century that Winter Park became a planned resort community. Northern business magnates seeking refuge from harsh winters envisioned a tranquil retreat amidst the natural beauty of Florida. They strategically developed the town, focusing on its grid-like street layout and creating a picturesque main street, Park Avenue.

As the 20th century dawned, Winter Park continued to grow and evolve. The establishment of Rollins College, a private liberal arts institution, added a cultural and intellectual dimension to the community. The city’s dedication to preserving its natural beauty and historic architecture has ensured its enduring appeal. Today, Winter Park remains a sought-after destination known for its lush landscapes, charming neighborhoods, and vibrant cultural scene.

Rollins Prank Ends Era of Altamonte Tram

From its founding in 1883 until 1925, a horse-drawn street car ushered guests from the train station to the Altamonte Hotel. The storied transport came to an abrupt halt.