The Jackson Homestead provides an excellent example of an upper-middle-class Federal house typical of rural communities near Boston. After serving in the Revolutionary War, Timothy Jackson inherited the family farm that included a 1670 house. Built five years before his death in 1814, the new dwelling personified his prosperous life as one of the town's leading citizens. In addition to serving two terms in the U.S. Congress, Timothy was an active abolitionist whose house provided a stop on the Underground Railroad. The five-bay facade, low-pitched hipped roof, and main entrance framed by a segmental arch and sidelights are very typical of the period. The end walls of the house are brick with a round arched doorway on both sides. The one-story portico in front of the main entrance is an original feature documented in an early daguerreotype of the property. The rear section of the 1670 house was retained and remodeled for the carriage house wing of the present building.
Timothy's eldest son, William, acquired the house in 1820. According to William Jackson's diaries, he added more elaborate interior woodwork. Several generations of Jacksons lived here until the 1930s when it was rented for a dental office. In 1949, descendants donated the house and many family furnishings to the City of Newton, and the property is now a house museum owned by the City of Newton and administered by the Newton Historical Society. Elements of the interior woodwork, such as fireplace mantels, had to be reinstalled or replicated when the house became a museum.