385 Beacon was designed by architect and builder Frederick B. Pope and built ca. 1869, probably for speculative sale, one of ten contiguous houses built as five symmetrical pairs (377-379-381-383-385-387-389-391-393-395). In his Houses of Boston’s Back Bay, Bainbridge Bunting indicates that the eight houses at 381-395 Beacon were built for “Jordan, Pope, Bealls, Cotting, et al.”
By 1871, 385 Beacon was the home of hardware and metal dealer Samuel May and his wife Helen (McClees) May. They had been married in January of 1871 and 385 Beacon probably was their first home together. He had lived in Dorchester before their marriage. Helen McClees (by her unmarried name) is shown as the owner of 385 Beacon on the 1874 Hopkins map. By 1875, they had moved to Dorchester.
By 1876, it was the home of banker Charles Emerson Fuller and his wife, Josephine (Wheildon) Fuller. They had lived at the Hotel Vendôme in 1875. They continued to live at 385 Beacon in 1878, but by 1879 had acquired and moved to 304 Beacon.
By 1880, it was the home of Mrs. Elizabeth Greenough (Lewis) Gay, widow of Dr. George Henry Gay, who had died in August of 1878. They had lived at 321 Marlborough prior to his death. She is shown as the owner of 385 Beacon on the 1883, 1888, 1898, and 1908 Bromley maps.
During the 1884-1885 and 1885-1886 winter seasons, she was traveling in Europe.
During the 1884-1885 season, 385 Beacon was the home of Catherine (Jarvis) Hunt, the wife of Leavitt Hunt, and their son, Jarvis Hunt, an architect. Their primary residence was in Weathersfield, Vermont.
385 Beacon was not listed in the 1886 Blue Book.
Elizabeth Gay had resumed living at 385 Beacon by the 1886-1887 winter season and continued to live there until her death in December of 1907. Her unmarried son, Ernest Lewis Gay, lived with her. He was an antiquarian and book collector.
After her death, 385 Beacon became the home of her son, Dr. Warren Fisher Gay, a surgeon, and his wife Ellen Freeman (Stickney) Gay. They previously had lived and he had maintained his medical office at 416 Marlborough (where he continued to maintain his office after they moved to 385 Beacon). Ernest Gay moved to 317 Marlborough. Warren and Ernest Gay are shown as the owners of 385 Beacon on the 1912 Bromley map.
Warren Gay died in August of 1916 and Ellen Gay moved to an apartment at 409 Marlborough. 385 Beacon once again became the home of his brother, Ernest. He died in November of 1916 on the special Harvard Train returning from the Harvard-Yale football game in New Haven. Ernest Gay is shown as the owner on the 1917 Bromley map.
385 Beacon was not listed in the 1918-1921 Blue Books.
By the 1921-1922 winter season, Warren Gay’s widow, Ellen Gay, was again living at 385 Beacon. In 1920, she had lived at 9 Massachusetts Avenue. Her son, George Henry Gay, is shown as the owner on the 1928 and 1938 Bromley maps.
Ellen Gay continued to live at 385 Beacon until about 1938, when she moved to Southborough to live with her son, George (she died there in January of 1939). She also maintained a home in Marblehead.
In April of 1938, 385 Beacon was acquired from George H. Gay by Agnes Mary (Amerault) Simons, wife of Dr. Sigmund Simons, a physician.
Sigmund and Agnes Simons lived in Westford and he initially used 385 Beacon as his Boston office. In the late 1940s, however, they moved to 385 Beacon and it became their home as well. They subsequently maintained residences in both Westford and at 385 Beacon.
Agnes Simons died in February of 1965, and Sigmund Simons died in July of 1995.
In June of 1996, Ann M. Geupel purchased 385 Beacon from the estate of Sigmund Simons.
385 Beacon remained assessed as a single-family dwelling in 2014.