Oak Hill Middle School has a rich and long history dating back to the 1900s. The school is located in the Oak Hill village in Newton, Massachusetts. Until 1920, the Oak Hill area was largely rural. With the population increasing and development taking place throughout the 1920s and 1930s, there was a need to build a new school. As early as 1929, Mayor Edwin O. Childs suggested that there was a need for a new school to serve the development at Oak Hill; however, land for a new school was only acquired by the city in 1935. The plan for the construction of the school also included space for a library. Construction was paid for in part by a grant from the federal government. The Oak Hill School and the library were constructed in 1936 and were designed by the firm of Densmore, Le Clear, & Robbins, a prominent local firm with many buildings in Boston and Cambridge. The original school was built on Wheeler Road based on a rectangular plan. The building had two stories and a basement, and it included a library wing (used today as an art room) on the east side connected to the school main building.
Like many of the school buildings of this time period, Oak Hill was built in the Georgian Revival style with distinctive architectural features and beautiful exterior details. It is constructed of red brick and trimmed with a cornice as well as a cast stone door and window surrounds. The main building includes a hipped roof, and the library wing has a gable roof. The main building has symmetrically placed doors at each side of the street. The entrance doors and the windows above the doors are set within cast stone surrounds, and the windows have cast stone sills.