Thomas Sherwin House // 1883

Tucked behind the St. John Episcopal Church in Sumner Hill, Boston, the Thomas Sherwin House sits atop the peak of the hill, and likely has views of downtown Boston from its upper floor. The house was built in 1883 for Thomas Sherwin, an auditor, and possibly the man of the same name who was a Brigadier General in the American Civil War. The home was designed by the powerhouse architectural firm of Ware & Van Brunt and spans two major architectural styles of the period; Stick style and Queen Anne. The home is one of the best examples in the neighborhood and is very well preserved!

Greenough-Fitzgerald House // 1893

David Stoddard Greenough IV (1844-1924), was a descendant of David Stoddard Greenough and Anne Doane, who acquired the Loring-Greenough House after it was taken from loyalist Joshua Loring. David Greenough IV became a businessman and real estate developer, following his father’s footsteps, after the development of much of the family land near the old homestead. It was David who sold the old homestead out of the family, likely for development, as Jamaica Plain had become a streetcar suburb, with many older estate lots subdivided and homes demolished for commercial buildings or smaller homes. Luckily, the old estate was purchased and saved by the Jamaica Plain Tuesday Club. This home built for David Greenough IV was constructed in 1893, possibly as a high-end rental property. The home is a blending of Queen Anne and Colonial Revival styles, which serves as a transition house from the Georgian style Loring-Greenough House to the intricate Queen Anne homes in the Sumner Hill neighborhood behind. The home was purchased by Susan W. Fitzgerald in the 1910s. Ms. Fitzgerald (1871-1943) is best known for her commitment to the women’s suffrage movement and her involvement in progressive political organizations, including sitting on the Massachusetts House of Representatives from 1923-1925.