Designed by Minneapolis architect A. R. Van Dyke and built in 1937, the house of Leal and Harriet Marston Headley at 815 East Second Street was patterned after Mrs. Headley's childhood home in San Diego, California. Mrs. Headley’s family had owned the popular and elegant Marston Department Store, a neo-Renaissance landmark in downtown San Diego.
Leal Headley, Carleton Class of 1907, had earned his MA and PhD at Harvard University and had come back to teach at his alma mater in 1911. He headed the college's education and psychology department until his retirement in 1952. During his long career, Leal Headley served as the college’s de facto admissions department, its appointment and placement bureau, and its public relations office. He also chaired the Northfield Hospital Board for twenty-five years and served as president of the Northfield Improvement Society.
Built on a sloping site overlooking Bell Field, which was created by D. Blake Stewart (Stewsie) in the 1920s with three teams of work horses, Headley House was constructed in the Arts and Crafts style, popular in California. With its orange tile roof and brick and stucco exterior, it appears smaller from the street than from Bell Field. During the 1930s, a Carleton student who lived on the lowest level traded shoveling coal into the furnace for free room and board.
In 1988, the Headleys gave the house to Carleton. Later, when the house served as a residence for the dean of the college, an addition was added to its east side.