The Chestnut Hill Historic District encompasses the historic portion of the village of Chestnut Hill that lies in Brookline, Massachusetts, with only slight overlap into adjacent Newton.

A small portion of the district extends south of Route 9, including a few houses and the Baldwin School on Heath Street.

[1] The oldest portion of Chestnut Hill, including its colonial roots, lies just over the line in Newton, and was also the part of the village that was the first to be developed as a suburban residential area.

The area was developed between then and about 1920, with large, high-quality houses on well-proportioned lots.

[2] Several prominent area architectural firms were engaged in the development of properties in the district.