The John Chesley Residence is notable for its presence in the Douglas Avenue Preservation Area. This Saint John streetscape is recognized and protected for its integration of the lower, middle, and upper classes. Built in the mid-1850's, Douglas Avenue was designed to connect the new suspension bridge at Reversing Falls to Saint John's Main Street. Thanks to its richly interconnected community, due in part to the spacious front lawns on the numerous properties, this avenue and some of the surrounding residential streets were highly popular during the late 1800s. Additionally, when streetcar transportation became accessible to Douglas Avenue in 1902, more and more members of the working class were drawn to the area.

The first block of Clarendon Street, which was established in 1909 and on which this house sits, is considered a part of the Douglas Avenue Preservation Area. Clarendon Street is recognized for its numerous Craftsman, Arts and Crafts, and other post-Victorian houses, and the John Chesley Residence, with its Craftsman-style design, two-storey square form, and front veranda, fits in perfectly with the surrounding buildings.

This residence was built for Agnes Collins, who is notable for her role as a devout member of St. Peter's Catholic Parish. Much of Clarendon Street once belonged to the parish, and many of its residents were active churchgoers. Outside of worship, she was also a member of a number of church-related organizations, including the Married Women's Holy Family and the Catholic Women's League.

Collins only lived in part of the building and rented out half the residence to John Carey Chesley, who served as an agent for the Federal Department of Marine and Fisheries for 24 years. In this role, Chesley maintained and gave recommendations on the navigational aids in Bay of Fundy, ensuring that the region's ports were accessible. Outside of work, he was a member of the Acadia University baseball team and helped to promote the sport in Saint John. Additionally, he spent many years on the Saint John Boxing Commission and had a six-year term as its chairman.