In 1915, George and Ellen Booth opened a portion of their property to the general public with the construction of a small Greek Theatre. In 1918, the Booths built the Meeting House, which became the Bloomfield Hills School, opening for local children in 1922 (grades 1–12).
 
Subsequently the Booths decided to build a middle school and a college preparatory school. Cranbrook School for Boys, which began operations in 1927, was designed by world-renowned Finnish architect Eliel Saarinen. Completed in 1928, it was Saarinen's first executed architectural work in the United States.[5] The name "Cranbrook" was chosen since Cranbrook, England was the birthplace of George Booth's father. Kingswood School Cranbrook (for girls), also designed by Saarinen, opened in 1931. Cranbrook and Kingswood enrolled students from grades 7–12. The Bloomfield Hills School became an elementary school and was renamed Brookside School Cranbrook in 1930.
 
Unlike the Cranbrook School for Boys, which has several buildings, the Kingswood School has only one building, which includes supporting facilities. It houses dormitories, a dining hall, an auditorium, classrooms, lounge/common areas, a bowling alley, and a ballroom. The education at Kingswood School Cranbrook was initially primarily viewed as a "finishing school".
 
For the Booths and Saarinen, the conception and design of the Cranbrook and Kingswood schools, were greatly influenced by the Arts and Crafts Movement, which began in 19th-century England.[6]
 
In 1923, Booth founded an Episcopal church to serve the nascent Cranbrook community, as well as surrounding communities. He chose the firm of Goodhue Associates to design the church. Groundbreaking took place in 1925, and Christ Church Cranbrook was consecrated on September 29, 1928.[7] Originally Cranbrook and Kingswood schools were affiliated with the Episcopal Church, but they have since secularized. However, special occasions are still celebrated at Christ Church Cranbrook.
 
Cranbrook School, Kingswood School, and Brookside School operated separately until 1970, when it was decided to govern them together. This was followed by the creation of the Cranbrook Educational Community. In 1985, Cranbrook and Kingswood schools were merged to create a co-educational upper school institution.
 
The middle school did not become co-educational; it was divided into gender-specific campuses in 1984. The Community acquired Vaughan School to house the boys' middle school. The basement of Kingswood was at one point the girls' middle school. A new Middle School building opened in 2010. For boys and girls of grades 6–8, all classes are separate. The exceptions are those for the performing arts (Symphonic Band, Orchestra, and Choir). English, religion, and history classes are taught separately to boys and girls through the 10th grade.
 
Architecture critic Paul Goldberger of the New York Times called the Cranbrook campus "one of the greatest campuses ever created anywhere".