Henry Burton Sterling was born in Halifax, Nova Scotia on 10 October 1871. He was the son of architect David Stirling and Clara Dean Richmond Lea. [There is some inconsistency in the spelling of the family name but Sterling has been chosen as this was the name that both Clara and H.B. Sterling appear to have adopted following David's death in 1887.] David Stirling was born in Galashields, Scotland in 1822. He practiced his profession in Halifax and branched to Prince Edward Island where he and his apprentice, W. C. Harris operated a firm known as Sterling and Harris. It was in Prince Edward Island that he met and married, on 1 December 1869, Clara Lea, widow of John Lea. Their son, known as Harry, was born two years later. Clara Dean Richmond was born in Winterport, Maine in 1826 and was married first to John Lea with whom she had a daughter, Ella May Lea (!860-1958) who married Edward Sherbourne Blanchard, M.D. (1849-1917), Superintendant of Falconwood Hospital. Ella and Edward had two sons, Edward Sterling (Bone) Blanchard and Aubrey A. Blanchard. Aubrey drowned at the age of 23 in 1905 but E.S. Blanchard became a well-known architect in Charlottetown from the 1920s to 1950s.

Presumably Clara and "Harry" moved to Prince Edward Island some time following David's death as they appear in the 1891 census of Charlottetown. Harry Sterling became an electrician and is said to have worked for the P.E.I. Electric Light Company on Water Street close to his home. He was an avid amateur photographer with a keen eye for composition and concentrated produced primarily on the buildings and streetscapes of Charlottetown but also took some photographs of Summerside and other smaller communities across the Island. Some of his work appears to have been used commercially, for sale and in postcards and tourist brochures.

He disappears from Island records about the turn of the century. He appears to have moved to Ontario where he married Edna Mae Slaght and had at least one child David who was born circa 1907 and was still living at the age of 91 in 1992.