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15 Weybridge Road was one of two houses on this street built by Daniel Heffernan and based on a design attributed to the Dix Lumber Company. The first residents listed in the Street List were Mary Gaffney, previously in Milton, and her daughter Katherine, a teacher, previously in New York. They were listed here in 1931 and 1932.

The Gaffneys may have been renting from Bartholomew Grady who was listed as the owner of the house on the building permit but was not listed as living at the house until 1933. Grady had been listed at the other Heffernan/Dix Lumber house, 35 Weybridge Road, in 1928, but was shown as living on Commonwealth Avenue on the 1930 permit.

Bart Grady, the son of Irish immigrants, was born c1873. He was a musician, listed in a 1903 Somerville directory as a pianist at Keith's Theater, and later became a theater manager. He and his wife Honora, or Nora (born c1882 in Vermont to Irish immigrants) had several children. Nora may have died before the family moved here. She was listed at 35 Weybridge Road in 1928, but only Bart and the two youngest children, Lawrence and Ann, were listed at this address.

Lawrence Grady (1908-1985) was an executive in private industry for many years before joing the Small Business Administration in the 1960s. He was one of the founders, at the SBA, of the Service Core of Retired Executives. Ann L. Grady (1910-2005), later Ann Fleming, graduated from Emmanuel College in 1931. She worked at the Salada Tea Company and taught at Cardinal Cushing Central High School. She was also active in the Emmanuel College Alumni Association. (Her older sister Mary (1906?-2001), who entered the Sisters of Notre Dame in 1928 and became Sister Ann Bartholomew Grady , was president of Emmanuel from 1960 to 1969.)

The Grady family was listed at this address from 1933 to 1937.

The next residents were Anna J. Connor and her three grown children, Howard, Sadie Eleanor, and Harold, who moved here from Boston. The Connors were all born in England and came to the U.S. in 1905. Anna Connor (born c1868) and her late husband also had three older children.

Howard C. Connor (1895-1963) was listed as an accountant in the 1920 and the 1930 U.S. Census. He was shown as an attorney in the Brookline Street List. Sadie Eleanor Connor (1900-1966) was listed as a stenographer. Harold E. Connor (1916-1992) was listed as a salesman until 1943 when he entered the U.S. Navy.

Members of the Connor family were listed at this address from 1939 until the late 1960s.