Construction of the High School started in 1894 and was complete in 1896. Due to Medford's growth as a suburb of Boston, the original brick building was nearly doubled in size in 1914 by the addition of a rear wing which contained many classrooms, a gymnasium and an auditorium holding 1,200 pupils (the rear addition was destroyed by fire in 1965).
Population growth required construction of a north wing in 1929 and, ten years later, a south wing. Along with classrooms and a gymnasium, the south wing also possessed an auditorium which was the largest of its kind in the Commonwealth of Massachusetts at the time of its completion.
Characteristic of their period, these wings are built of red brick trimmed with cast stone details that combine elements of the Renaissance Revival and Colonial Revival styles. Together with the Medford City Hall, the wings of the high school are the finest local examples of their style.
After the fire in 1965, only the north and south wings remained in use until 1971, when the new high school on Winthrop Street was completed. The Old Medford High School was only lightly used for municipal offices after that, and was largely abandoned by the late 1970's.
In October 1983, the property, then still owned by the City of Medford, became listed with the National Register of Historic Places. About a year later, Medford sold the property to a developer for conversion to condominiums.
In January 1995, the unit owners assumed majority ownership and control of the Association.