Giles, an Amelia native and the son of Virginia governor William Branch Giles, was a lawyer with a keen interest in architecture and some skill in its practice. With the help of architect and civil engineer Percival of Richmond, Giles produced the design of Winterham for his cousin John Garland Jefferson and his wife, Otelia Howlett. The house was once part of the Jeffersons' twelve-hundred-acre plantation. The two-story frame house has elements often featured in the work of Samuel Sloan—Italianate with boxy, symmetrical massing, a deck-on-hip roof with deep eaves supported by brackets, eared architraves around the openings, and slender, paired porch columns on the small entrance portico. Winterham is now a bed-and-breakfast. Across the road on land that was once part of the Winterham property is a large twentieth-century gambrel-roofed frame barn with silos set at each end.