Moving from Ocala to Jacksonville in 1902, Roy A. Benjamin is credited with the design of many notable buildings, particularly theaters, in Jacksonville and throughout the southeast. In Jacksonville, Benjamin was the architect for the Imperial Theatre (demolished), the Palace Theatre (demolished), the Riverside Theatre, the San Marco Theatre, the Arcade Theater, as well as serving as associate architect for the Florida Theatre.

Being one of Jacksonville’s most prolific and talented architects, Benjamin designed many other significant buildings in Jacksonville. These landmarks include the Elks Club Building, Otis Elevator Building, Fire Station #4, Leon Cheek Residence at 2263 River Boulevard, San Juline Apartments at 1617 – 1637 Riverside Avenue, Memorial Park in association with the Olmsted Brothers, Fenimore Apartments at 2200 Riverside Avenue, Hartimore Apartments at 2970 Riverside Avenue, the Park Lane Apartments at 1846 Margaret Street, the Lauderdale and Avondale Apartments in Springfield, Scottish Rite Masonic Temple, and the Elephant House at the Jacksonville Zoo (demolished). Several of these buildings and Memorial Park were designed in association with other architects, particularly Mellen C. Greeley who was Benjamin’s partner from 1919 to 1924.

When he retired after World War II, Benjamin sold his practice to William D. Kemp, Franklin S. Bunch, and William K. Jackson. The firm continues today as KBJ Architects, Inc. Benjamin constructed his own home in the neighborhood at 2332 Riverside Avenue. Constructed in 1921, this house has since been demolished. Benjamin died in 1963.