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The Chestnut Hill School was founded in 1860 through a bequest in the will of Thomas A. Lee. Designed in the style of the Old Ship Church in Hingham, Massachusetts, the original school building was a chapel built with wood from chestnut trees on Hammond Street and Chestnut Hill Road. In 1863 the original one-acre property was deeded to a self-perpetuating Board of Trustees for the religious and educational benefit of children in the immediate local area. In the early years the school served children in the primary grades only, eventually extending to grade 6 in 1968.

In recent decades The Chestnut Hill School has extended its reach far beyond the local community, consistently drawing families from 35 communities in the Greater Boston area. Diversity of all types is highly prized: cultural, ethnic, racial, religious, socio-economic, geographic, and sexual orientation. Boasting a richly diverse population of families and staff members, the school strives actively to integrate multicultural perspectives both into curricula and community life. Thanks to a strong culture of family involvement and a highly energized Family Association, volunteerism abounds.