This thesis examines the life and work of Hiram Halle (1867-1944), a self-made businessman who remodeled over thirty historic houses in Pound Ridge, New York, during the 1930s. Halle adapted the Colonial Revival style to suit his own aesthetic ends, incorporating salvaged material to create distinctive houses with broad appeal. Despite their historic veneers, Halle's houses reflect a progressive approach to design, with an emphasis on functionality and versatility. Halle also shaped the town's social environment by renting his houses to people he felt would make positive contributions to the community. At a time when anti-Semitism prevailed, Pound Ridge became known as an inclusive place under his influence. Halle's life and his material legacy in Pound Ridge have received little attention. This thesis investigates Halle's houses as material culture, artifacts which reflect the cultural conditions that shaped their creation. In combining progress and preservation, high style and homespun vernacular, colonial conservatism and immigrant flair, Halle's houses represent many of the cherished ideals and salient contradictions of America, and Americans.