Sterling Bradley was a well-known citizen in nineteenth-century Hamden, who served as a selectman in 1832, 1833 and 1834. In 1829, he inherited the second of two houses built by his father, Amasa Bradley, on Whitney Avenue in the Mount Carmel section of town. As described in The Connecticut Quarterly, Vol. IV, No. 4 (1898):
Sterling Bradley, a life-long resident of Hamden, became the sole proprietor of the Cheshire turnpike during the latter part of the time when toll was collected. His stalwart form was a familiar figure, usually accompanied by a team of unusually fine oxen. At one period his home became the country tavern that furnished refreshment to the throngs of people that traveled over his road.
As described by John H. Dickerman in the Colonial History of the Parish of Mount Carmel (1904):
Sterling Bradley, whose houses and barns still stand as he built them on the old colonial highway, afterward the turnpike, was an early promoter of choice cattle. His Durham stock long held precedence in the town, and his name became proverbial as associated with fine oxen. It was the custom at the County fair to award a liberal premium to the most numerous and best team of oxen exhibited by any town within the county. The team started at or near the home of Sterling Bradley and continued to augment as it proceeded through the town until one hundred and twenty-five yoke of oxen were gathered in the “round up” on New Haven Green. Mount Carmel always carried home the banner of victory when an effort was made to get out its full quota.
While continuing to operate the tavern in the house built by his father, Sterling Bradley built a new house, around 1835, across the street, at 3997 Whitney Avenue.