The Dillaway School is located in Boston's Roxbury neighborhood, a short way west of Nubian Square (formerly Dudley Square) on the south side of Kenilworth Street near its junction with Dudley Street.

The entrance is in the center bay, recessed under an elaborate stone arch, above which is a complex multipart round-arch window assembly.

[3] This school was built in 1882 to a design by George Clough, who was the first Boston city architect.

He entered this role in 1875, by which time the city had grown by annexation nearly to its present size.

Clough designed many public buildings for the city as a result of this growth and his position.