Daniel Heald, one of the earliest settlers in the town of New Flamstead (Chester), established his farm on the west side of the upper Williams River. He served as town clerk from 1779 to 1799 and as town representative from 1783 to 1797. Around 1785, he built the first wood-frame house in North Chester, a two-story, central-chimney house. Between Heald's house and the bridge across the river, Heald's son Amos built one of the earlier brick dwellings in eastern Vermont. This 1803 building has a Georgian plan and end-wall chimneys. It may be the work of Captain William Dana, who lived in nearby Springfield and was responsible for most early brick houses in the area. Dana's brick house with similar flat arches was built in 1809 on South Street Extension in Springfield. To the 1803 building here, Amos Heald added the long attached wood-frame ell and barn with its row of segmental-arched wagon bays, a good early example of the connected-architectural arrangement that became popular throughout eastern Vermont. He, too, served as town clerk, from 1826 to 1848. After his death, his son Prescott took over the property and probably built the small one-room wing on the north gable end of the house, which became the town clerk's office during his tenure, as well as the office for his insurance business.