Edmund Wheelwright served as Boston city architect from 1891 to 1895, designing fire stations, police stations, park buildings, and schoolhouses of distinction. The Bowdoin School represents the issues he espoused in his 1901 book, School Architecture, such as using the Federal Revival here to relate to the surrounding environment and to reinforce the importance of native Boston traditions for the immigrant children attending this school. The brick with limestone–trimmed school commanded a steeply sloping site, allowing two classrooms at the basement rear of the building, a library on the second floor, and an assembly room at the top level, which complemented the generously scaled classrooms. Like many redundant institutional buildings, the grammar school became the Bowdoin School Apartments in 1977.