The Levy-Gresham House was built in 1912 by Henry H. Levy (1874-1959), a local Jewish merchant who worked at I.C. Levy’s with his father, I. C. Levy, who lived across the street in his Queen Anne Victorian Levy House. Some reports suggest that I. C. Levy himself built this home. While its possible the elder Levy financed the house, the only name on the original deed is his son Henry Levy.
Henry Levy died in 1959, and his widow continued to live here until 1965, when she sold the house to H. S. Nichols. After less than one year, Nichols sold the house to Steven B. Gresham and his wife Frances, who have lived in this house since then, for over 50 years.
The Levy-Gresham House is likely one of the earliest Craftsman houses built in Holly Springs, and might be the archetype of the Craftsman style in Holly Springs. In fact, the house contains several architectural elements from the earlier Colonial Revival style, including two Tuscan colonettes (rather than the more standard square posts found on other local Craftsman houses).
The Levy-Gresham House is a one-and-a-half-story flanking-gable brick Craftsman Bungalow, with a prominent four-bay gable-front porch with exposed purlins and struts supported by brick corner piers on top of an enclosed balustrade. An eyebrow dormer is located in the middle of the roofline.