William Hyslop Sumner House // 1852

One of the oldest extant homes in the Sumner Hill neighborhood of Jamaica Plain is this stunning 1852 country mansion, built for William Hyslop Sumner. General William H. Sumner (1780-1861) was born in Roxbury, not far from where he built this house in his later years of life. He attended Harvard College, and after graduating, Sumner entered the law office of district attorney John Davis, gaining admittance to the bar in 1802. He practiced law from 1802 until 1818 when he left the field in order to concentrate on his military duties at the outbreak of the War of 1812. Sumner was involved in the state’s defenses. In September 1814 Massachusetts Governor Caleb Strong sent Sumner, then a lieutenant colonel in the state militia, to coordinate the defense of Portland in the District of Maine (which was then still a part of Massachusetts). His task was to maintain 1,900 militia and create a better relationship between the Massachusetts militia and the U.S. Army forces posted there. After the war, he developed what we know today as East Boston. His maternal grandmother, Mehitable (Stoddard) Hyslop, owned Noddle’s Island. Sumner’s Beginning in 1833, in partnership with Stephen White and Francis J. Oliver, The East Boston Company was created to conduct the development of East Boston. They laid out the first planned neighborhood in the City of Boston, laying out grids and house lots. He would go on to write histories on the neighborhood which are referenced to this day. His country estate in Jamaica Plain is a blending of Greek Revival and Italianate styles. The home is undergoing a renovation currently.

Webster-Jenkins Mansion // 1875

One of my favorite homes in Jamaica Plain is this gorgeous old Victorian-era home, perched high on Sumner Hill. The house was built in 1875 seemingly for John L Webster and his wife Henrietta with John as the architect/builder. John built other homes in the neighborhood, and clearly did well for himself as he acquired one of the most prominent sites in the area for his own home. After his death in 1890, the home was willed to his daughter and her husband, Augustus T. Jenkins, who worked as a Clerk in Downtown Boston. The house blends many mid-to-late 19th century styles including Second Empire, Stick, and Victorian Gothic, and is among one of the most architecturally pleasing I have seen. The central tower, obscured in my photos by trees, probably provides some amazing views of the growing city in the distance.

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.