Just northeast of downtown Orlando, Winter Park is home to some of the area’s finest homes. Most neighborhoods are well established. There is great diversity in the style and size of homes including Bungalows, Craftsman, Ranch, Georgian, Mediterranean, Italian, Cape Cod and New Orleans styles. In many cases older modest homes have been razed and replaced with stately residences.
Once a major citrus-growing region, Winter Park was a popular retreat for well-to-do Northerners who traveled south by train in the early 20th century. From those roots, a city sprang up where culture thrived and natural resources were well protected. Today, Winter Park is 8 square miles (20.7 square kilometers) with 20,000 oak trees and is home to almost 28,000 residents. One of the best ways to get a peek at the Winter Park lifestyle is on the Scenic Boat Tour, a local attraction for more than half a century that takes visitors past lakefront mansions and through the city’s historic canals.