The Benjamin Flagg House is a historic house located at 136 Plantation Street in Worcester, Massachusetts . Built c. 1717, it is considered the oldest structure in the city. It was home to a number of generations of influential Flaggs, including American Revolutionary War Captain Benjamin Flagg (1724–1818). [ 2 ] The house was listed on the National Register of Historic Places in 1980. [ 1 ] Description and history The Flagg House occupies a triangular lot on Worcester's east side, bounded on the west by Plantation Street and on the east by Ingleside Avenue. The house is a 2 + 1 ⁄ 2 -story wood-frame structure, three bays wide, with a side-gable roof, large central chimney, and clapboard siding. Its center entrance (facing west toward Plantation Street) has modest trim, with a four-light transom window above. [ 2 ] The house is assumed to have been built about 1718, when Benjamin Flagg II purchased a large tract of land in the area; however, it is not known how much of the building is his original construction, and how much may have been later alteration. [ 2 ] According to Caleb Wall's Reminiscences, Flagg's son, also named Benjamin, "commanded the company of militia, who marched with Col. Timothy Bigelow 's company of minute men for Lexington , on the alarm, April 18, 1775 , afterwards Colonel in the revolutionary service, filled important town offices, and died in Worcester, October 8, 1818, aged 95... Col. Flagg's location was on Plantation Street, on a farm of 150 acres..." [ 3 ] The house was sold out of the Flagg family in 1850. [ 2 ] National Register of Historic Places listings in eastern Worcester, Massachusetts 1 2 "National Register Information System" . National Register of Historic Places . National Park Service . April 15, 2008. 1 2 3 4 "NRHP nomination for Benjamin Flagg House" . Commonwealth of Massachusetts . Retrieved April 14, 2014 . ↑ Wall, Caleb. Reminiscences of Worcester . 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