The College Quarter Historic District sits on the slope and plateau above the northwest shore of Lake Virginia. In the pre-settlement period, the land nearest the lake was covered with cypress, water oaks, and hickory trees while the uplands were home to tall pines, live oaks and saw palmettos. The neighboring Rollins College campus began developing in the mid-1800s shortly after the town was founded. The area of the historic district was cleared and planted with orange groves. Residences were few and scattered for the first decades. The “Dinky Line” railroad tracks, since abandoned, ran along the shore of Lake Virginia.
The early subdivision and residential development of the College Quarter that took place during the first half of the twentieth century provides the historic architectural context for the historic district. The historical development of the College Quarter covers the periods of Florida history from the Florida Land Boom, the Great Depression and New Deal, and World War II and aftermath. J. A. Treat subdivided College Place in 1921 and J. E. Trotter subdivided Trotter’s Replat in 1925. The houses that were built served as year-round residences for local businessmen and educators rather than as winter retreats. This is indicative of the growing economic maturity of Winter Park.
The College Quarter Historic District is important for its collection of historic architecture, which was built during the years from 1920 to 1953, and for its early subdivision style street pattern. The historic architectural styles found within the College Quarter Historic District are representative of its period of historic development. They include but are not limited to Craftsman Bungalow, Mission Revival, Mediterranean Revival, Colonial Revival, Vernacular and Minimal Traditional styles.
College Quarter Historic District encompasses the 1921 College Place subdivision, the 1925 Trotter’s Replat subdivision, the Mrs. L. A. Dennis subdivision, and subdivided portions of the Town of Winter Park. The neighborhood generally extends from the western border of Rollins College on French Avenue to Pennsylvania Avenue, and from Lake Virginia and the (WPHS) Ninth Grade Center to Holt Avenue.