Rollinsford Grade School is eligible for the National Register of Historic Places with statewide significance under Criterion C as an early and well-preserved commission of the New Hampshire architectural firm of Huddleston & Hersey. Rollinsford Grade School was the prototype of the firm's Colonial Revival design school that was used on at least 14 other schools in New Hampshire and Maine and modified for a town hall in Berwick, Maine. Rollinsford Grade School is also eligible with local significance under Criterion A for its associations with education and with politics & government. Constructed in 1936 to consolidate the town's two surviving one room schoolhouses and a four room village school, Rollinsford Grade School continues to serve as the town's only active school building. The school was constructed with funding from the Public Works Administration or PWA. Rollinsford Grade School, one of only two substantial structures built in Rollinsford using PWA money, is the only extant example in the town of a building that utilized "New Deal" programs in its construction.

The gravestone is for the Cocker Spaniel Obo II who was imported from England in 1882 by James P. Willey. Obo II is credited as the father of the American Cocker Spaniel. Although the grave marker predates the construction of Rollinsford Grade School the stone, which sits on the southwestern edge of the playground, has been and continues to serve as a traditional gathering spot for school children during recess and after school, even when this practice was discouraged by the school faculty.