An old estate property was purchased and the school opened in the converted stables in September 1957.

[citation needed] Brookwood School had an initial enrollment of 65 students in 1957.

[3] Brookwood's Board of Trustees is the governing body, managing the school's financial and physical resources.

[6] The campus consists of 30 acres (12 ha) of playing fields and academic buildings, surrounded by natural woodlands, slightly in-land from the northern shore of Massachusetts Bay.

The upper school students are housed in the wing that was originally the stables.