When first listed on the National Register of Historic Places in 1986, the district extended along Hammond Street, between Beacon Street and the MBTA Green Line right-of-way, and along Chestnut Hill Road between Hammond and Essex, including properties along a few adjacent streets.

[2] The district consists of a residential enclave of high-quality architect-designed residences on ample, landscaped lots, that exemplified the development of Newton as a fashionable upper-class suburb.

The area's colonial history begins with settlement in the 17th century by Thomas Hammond and others.

A station designed by H. H. Richardson was built at Chestnut Hill in 1883 and landscaped by Frederick Law Olmsted; it was demolished in 1960.

The 98-acre (40 ha) district includes 132 buildings, of which 109 contribute to its significance.