Chestnut Hill covers adjacent architecturally distinctive neighborhoods in both Brookline and Newton. The principal early-nineteenth-century landowner, Francis Lee, first developed the land in Newton in 1851. Brookline's portion of the Lee family landholdings was not sold off until the 1880s, at which time the first houses were built. Chapman and Frazer designed thirty-one of the early upper-middle-class homes built for Boston businessmen in variations of the Shingle and Tudor Revival styles. John Chapman died in 1895, so the majority was the work of Horace Frazer, whose own 1890 house is at 471 Heath Street (NRD). In close proximity to Frazer's house are seven other houses built by the firm in the 1890s: 1083 Boylston Street, 1106 Boylston Street, 1140 Boylston Street, 83 Dunster Road, 464 Heath Street, 476 Heath Street, and 63 Norfolk Road (all NRD). The largest Chapman and Frazer commission in this section of Chestnut Hill was the Wright Estate, with its surviving carriage barn (NRD), now used by the Brookline Recreation Department, at 652 Hammond Street.
Similarly, Putnam and Cox designed seven houses in Chestnut Hill, including William Putnam's residence at 91 Spooner Road (NRD). Andrews, Jaques and Rantoul designed five houses, including Herbert Jaques's own house at 50 Dunster Road (NRD), now gone. The carriage barn survives as part of the new Longyear Museum, a two-story hipped-roof building with deep eaves and arcaded entrance porch designed by Stopfel Architects in 1996–1999.