Located on Sewall Avenue in Brookline, Massachusetts, the Charles P. Flagg House exemplifies upper-class single-family housing built in the late 19th century that has been added onto and converted into multi-family housing to serve a growing city. Charles Partridge Flagg (1851-1911) was a real estate developer and head of the D. F. Flagg & Co., a wholesale liquor company his father started in Boston. He purchased the former Dexter property, subdivided the estate, and hired architect Julius A. Schweinfurth to design a home for his family. “Jule” Schweinfurth was long-associated with the firm of Peabody & Stearns of Boston, which in the late 19th century, was one of the premier architectural offices in the United States, but when he was not offered a partnership offer by his bosses, he established a new firm under his name. For the Flagg House, Schweinfurth blended the Shingle, Queen Anne, and Arts and Crafts architectural styles with a unique asymmetrical roofline, wide overhanging eaves with cross brackets and exposed rafter tails, consistent shingle siding, and a two-story polygonal oriel with domed roof at the corner. The Flagg House was moved forward on the lot to facilitate a rear addition and completely renovated in 2011, transforming it into a seven-unit condominium building with garage and elevator. This example of “gentle density” is exactly what communities should allow for, to preserve the character at the streetscape but provide additional housing.