By the mid-1800s, Pawlet had 10 one-room schoolhouses, and the Braintree School was built in 1852 to replace an earlier wooden structure that had burned. It stands in the small settlement of Braintree, named for New Braintree, Massachusetts, where its original settlers came from. The school served 8 grades for 87 years, with 9 to 14 students each year. It is a one-story, gable-front Federal Style school with double wythe rose brick walls laid in five-course American Bond, along with a gable-front woodshed and a two-bay outhouse behind the building. In 1930, town- and state-funded improvements probably included the bank of four windows on the west side and the addition of the side door. The school retains its original wide-board blackboards, typical of early period schoolhouses, and heat was provided by an Ajax wood stove that remains in the building. The property was placed on the National Register of Historic Places on May 3, 2010.