Chamberlain-Flagg House

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The Chamberlain-Flagg House is a historic home at 2 Brookshire Road in Worcester, Massachusetts, near Flagg Street. It’s one of the city’s oldest houses and is among the best-preserved 18th‑century homes. The exact construction date isn’t certain, but it’s believed to have been built in the mid-1700s on land once owned by the Chamberlain family, with later ties to the Flagg family. By 1800, the house belonged to Elisha Flagg, whose wife came from the Chamberlain family. The house was added to the National Register of Historic Places in 1980.

Architecturally, it’s a timber-frame, 2½-story structure with a gabled roof and clapboard siding. There are two chimneys—one through the center of the front roof face and another on the right end. The main facade is three bays wide, with windows placed slightly off-center around the center entrance. The doorway is a 20th-century Colonial Revival style with sidelights and a large gabled hood. A two-story ell extends to the left, and a screen porch is on the right. The house’s design echoes the area’s earliest settlers, with some features indicating 18th-century alterations.