The Chestnut Hill section of Newton predates its adjacent Brookline counterpart and consequently has more varied architecture. The original settlers were the Hammonds, who built farmhouses that still stand at either end of the street that bears their name. At 26 Hammond Street is the Judge John Lowell House, erected by either John or Nathaniel Hammond in 1735. After Boston merchant Francis Lee built the first country house nearby in 1854 (demolished), John Lowell acquired this Hammond Street house. Lowell, like several other wealthy Boston families, acquired tracts of land large enough for other family members to build houses. In 1884 Lowell erected a house and carriage barn for his son John on this property (517 Hammond Street, NRD) to designs by William Ralph Emerson, his wife's first cousin. Although the house is set back from the road and difficult to see, the carriage barn is directly adjacent to Hammond Street.
At the north end of Hammond Street adjacent to the corner of Beacon Street lies the other Hammond family house (9 Orchard Road, NR/NRD). William Coburn acquired the house in 1919 and hired renowned authority on colonial architecture Joseph Everett Chandler to undertake extensive renovations. Chandler's work was further embellished with additions made in 1930 by Harold Field Kellogg. On the other side of Hammond Street, Appleton and Stephenson designed the Dr. Daniel Slade House (1879), a symmetrical interpretation of brick eighteenth-century architecture and terra-cotta ornamentation having English Queen Anne motifs (538 Hammond Street, NRD). A noted naturalist, Dr. Slade helped found the Appalachian Mountain Club and the Hammond Pond Preserve in Chestnut Hill.
Just beyond the Slade house heading toward Newton looms the large stone house that Peabody and Stearns designed for William R. Dupee in 1880 (400 Beacon Street, NR). Constructed of local stone with brick lintels, Dupee's house features a large veranda looking south toward Hammond Pond. Mary Baker Eddy, founder of the First Church of Christ, Scientist, purchased the house in 1907. Mrs. Eddy, who lived the last two years of her life here, hired Chicago architect S. S. Beman to build a large stone carriage house with servants' quarters and make alterations to the mansion. Now open as a house museum, Mary Baker Eddy's residence contains much of the original Peabody and Stearns woodwork, although the furnishings reflect her brief occupancy.
Hammond Street connects Beacon Street with Boylston Street, forming the spine of the Chestnut Hill neighborhood. The neighborhood did not begin to be intensively developed until the early 1880s, at which time a commuter railroad was established with a stop at Chestnut Hill. The widening of Beacon and Boylston streets within the next ten years further augmented the growth of Chestnut Hill. On both sides of Hammond Street, and on the side streets to the east and west, large turn-of-the-century houses rose, designed by prominent Boston architects. Chapman and Frazer designed the major remodeling to the Edwin S. Webster House (307 Hammond Street, NRD) in 1905. This 1896 house by Wales and Holt was enlarged with a gambrel roof, porte-cochere, and other Colonial Revival–style improvements. The same firm planned the massive Spanish Mission–style house for Clement S. Houghton in 1900 (152 Suffolk Street). Houghton maintained one of the largest estates in Chestnut Hill and was responsible for the wildflower garden that is now part of the Webster Conservation Area.
Other large houses by prominent