Edward Hopper first visited Gloucester, Massachusetts, in 1912 while painting with fellow artist and friend Leon Kroll. He returned to Gloucester several times in the 1920s, following in the footsteps of earlier generations of American artists such as Sanford Gifford, Winslow Homer, Childe Hassam, and Maurice Prendergast. Like his predecessors, Hopper appreciated the intense sunlight and natural coastal beauty of the region and was particularly drawn to its local New England architecture. This is evident in the present drawing, House in Gloucester, which depicts a clapboard house from a low vantage point on the road.

Hopper often used sketches—or a compilation of sketches—to explore subjects, compositions, and lighting effects that would later become his watercolors or oil paintings. He frequently portrayed the everyday architecture of New England, and scholars have noted the portrait-like quality he brought to these depictions. House in Gloucester showcases Hopper's skill as a draftsman and his fascination with Gloucester's architecture. Working from observation, Hopper typically sketched in quick, improvisational strokes, creating varied effects in line and texture that captured the essence of the scene. In this drawing, Hopper contrasts the manufactured structures of the fence and clapboards—rendered with straight, thin lines—with the shaded, vertiginous areas of trees and plants. Hopper created hundreds of informal sketches throughout his career, using materials such as pencil, chalk, charcoal, and crayon. While a large collection of his drawings was bequeathed to the Whitney Museum of American Art, New York, additional examples of his charcoal drawings of houses in Gloucester are held in the collections of the National Gallery of Art in Washington, D.C., and the Amon Carter Museum of Art in Fort Worth, Texas.