Dexter Southfield School

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The Dexter Southfield School is an independent co-educational day school located in Brookline, Massachusetts, educating students from pre-kindergarten through twelfth grade. Dexter Southfield was founded in 1926 as the Dexter School. In 2013 the Dexter School merged with the sister school Southfield School to form Dexter Southfield with which it had shared its campus since 1992.[2]

Dexter Southfield School
Dexter Southfield School Shield.jpg
20 Newton Street


United States
TypePrivate, Independent
MottoBest Today, Better Tomorrow
Religious affiliation(s)None
Founded1926 – Dexter School
1992 – Southfield School
Head of schoolTodd A. Vincent
Student to teacher ratio7:1[1]
Color(s)Crimson & Navy
NewspaperThe View
Annual tuition$50,175 (grades 9-12)[1]


The Dexter School was founded in 1926 in response to the closure of the Noble & Greenough Lower School and lack of educational opportunities for boys in the Brookline area. The Dexter School opened on Freeman Street in the affluent Cottage Farm neighborhood educating boys through ninth grade. The school developed a strong bond with many of Boston’s leading families with ties to the leading preparatory and Ivy League schools. In 1966, Dexter sold its campus on Freeman Street and moved to their present location on a hill on Newton Street on the South Brookline/Jamaica Plain line. The school bought the property from the Catholic Foreign Mission Society of America who had resided on the site since 1945. The property was the former estate of Richard and Anna Sears, who had built a Mediterranean Revival Style villa on the site in 1928. As Dexter expanded, the school continued the style of the white stucco façade and red terra-cotta roof of the Sears House. Today, the original house remains the central structure on campus and houses the Senior Lounge, Business Office and Admissions Office. In preparation for the school’s move in 1968, the A building, Fisk Hall, and pool and gymnasium were built to the west of the Sears House. The Thorndike Hockey rink was added to the campus in 1973. From its long tradition as a boy’s lower school, Dexter has undergone a vast transformation over the last 25 years. In the 1990s, further additions were made to the campus including the construction of the Mid-Rise and original lower school building. In 1992, the Southfield School was established on the same campus to expand Dexter’s educational philosophy to young girls. In 2002, the Upper School was established to enable both the Dexter and Southfield schools to continue the school’s mission into the competitive secondary school market. The Clay Center was also constructed to the east of the Sears House greatly altering the school campus. The new center included a new auditorium, dining hall and fifth floor observatory. In 2011 Mr. and Mrs. William Phinney, who had led the school since 1964, and oversaw its move and expansion, retired after 47 years at the school. In 2013, the school was rededicated as the Dexter Southfield School, after received formal accreditation from the New England Association of Schools and Colleges (NEASC) Today, Dexter Southfield students offers single-sex classrooms in Pre-K through 8 and co-education in grades 9 through 12.


The 36-acre campus on the Boston-Brookline border included buildings such as Fiske Hall and the Sears Building grace the campus. Of particular note is the Clay Center for Science and Technology which provided students with classroom opportunities as well as an astronomical observatory.


Dexter Southfield School's curriculum includes arts as painting, wood shop, choir, and much more. Beginning in Kindergarten 2, each homeroom does one public speaking event per year. Starting in sixth grade, every student takes Latin through eighth grade. When in seventh grade, each student takes Latin and a modern language. Every student in the 7th and 8th grades is required to take a language and all students take six classes in grade 8. In the high school, there are approximately fifteen AP courses offering anything from AP Physics to AP European History to AP Latin. There are also honors and normal level classes for most courses. There were many upper class electives in history, English, and science.

Dexter Southfield's Sears House


Dexter's Varsity Tennis in 2012 was in NEPSAC Class A and beat teams like Phillips Andover and Phillips Exeter and advanced to the semifinals of the Class A tournament. The Varsity Hockey team is year after year one of the strongest in New England competing against teams like Cushing, Nobles, Exeter, KUA, and St. Pauls. The Varsity Hockey, Lacrosse, Tennis, Football, and Baseball teams have all had many athletes continue their careers at the Division 1 level of NCAA sports.

Upper School Sport Offerings

  • Fall: Cross-Country, Football, Soccer, Volleyball
  • Winter: Hockey, Squash, Swimming, Basketball, Curling
  • Spring: Golf, Crew, Tennis, Lacrosse, Baseball, Track and Field

Athletic Facilities

  • Darlymple Gymnasium (Basketball Court, Lockers)
  • Athletic Arena and Fieldhouse (Ice Rink, Basketball Court, Weight Room, Athletic Training Facility, Indoor Turf, Gym, Locker Rooms)
  • Fuller Field (Soccer, Lacrosse)
  • Cornish Field (Football, Field Hockey)
  • Charles River Boathouse (Crew)
  • Southfield, Farm Field (Multipurpose)
  • Lincoln Pool (Swimming)
  • Baseball Field, Softball Field


Every year in the grades K–8, the New Boy Assembly was held during the second week of school in Fiske Hall to welcome all incoming Dexter students to the school. Also, Dexter Day is held during October is essentially the schools homecoming as both the varsity football and soccer teams have home games where many students, faculty, alumni, and fans come out on a Saturday to support the school. Field Day was held in May where students K–8 compete in track and field events such as cross country, sprints, long jump, high jump, relay races, and many more. Also, every boy in grades 3–6 are assigned to either the Massasoit or Mohawk team for intramural sports. Prize Day was the last day of the school year for students K–8. In the high school, traditions such as the Fall Pep Rally before Dexter Day and Senior Prank Day have brought much fun to the community. Every Wednesday morning, each student in grades 6–12 met in Fiske Hall for a chapel procedure. Grades 1–5 met on Friday mornings for the chapel procedure. There are Bible readings, an inspirational story was told by a student, and the school prayers. Each student would sings along with song cards.

Notable alumniEdit