Five-Nine on Roosevelt occupies a building constructed in 1957 as a junior/senior high school for children on the American Fort Pepperrell Air Force base. It was one of the last buildings to be constructed on the 1940’s era base. It is a brick-clad steel and concrete structure, reputedly built to provide shelter from a nuclear attack if necessary.

By 1960 the building was vacated by the Americans and granted to the provincial government. In 1968 it was re-purposed as the Children’s Rehabilitation Centre, providing hospital and outpatient therapy for victims of polio and other disabilities. When this function was transferred to the newly built Janeway Hospital in 2001, the building again became vacant. In 2006 the Gilbraltar Development Corporation acquired the property, and re-developed it as a complex of varied and stylish condominium units. These have been occupied since late 2007. The owner governed condominium corporation assumed control in mid-2008.