High atop Mount Walley stands Dexter Southfield School a place steeped in history. Its grounds were once home to a Mediterranean Revival style villa built in 1924 for Anna Sears. The Catholic Foreign Mission Society of America resided there from 1945 until Dexter School acquired the property in 1966. This wasn’t just any move. It marked a significant expansion for Dexter. The school had originally opened in 1926 to address a lack of educational opportunities for boys in Brookline. Its early years saw notable students including John F Kennedy and his brother Joseph P Kennedy Jr.
The move to Mount Walley wasn’t simply a relocation. It was the beginning of a transformation. The school meticulously preserved the Sears House integrating it into its campus. The original structure now houses the Senior Lounge Business Office and Admissions Office. Expansions continued throughout the years. New buildings like Fiske Hall a gymnasium a pool and later the Clay Center with its observatory were added. The addition of the Southfield School in 1992 marked another milestone. It expanded the school’s reach to young girls.
Dexter Southfield’s story isn’t just about buildings. It’s about people. Mr and Mrs William Phinney dedicated 47 years to the school overseeing its dramatic growth. They even witnessed the school’s rededication in 2013 after it officially merged with Southfield School and received accreditation from the New England Association of Schools and Colleges. The school continues to thrive on Mount Walley. It boasts impressive athletic programs particularly its hockey team. A walk through its grounds provides a journey through time. You see the evolution of a school and the impact it has had on generations of students and the community. Each building at Dexter Southfield School speaks of its history. Mount Walley is more than a hill it is the foundation of a legacy.