From its inception, South Kent School was intended to offer a service-oriented education "at minimum cost for boys of ability and character, who presumably on graduation must be self-supporting.

The Straight farm was purchased from members of the Judd family, and additions to the farmhouse were made to house a chapel, twenty-four students, and faculty.

[12] South Kent is a college-preparatory school; the course of study is designed with the intent that every student will continue his education at a higher-level institution.

[13] Accelerated courses, including advanced placement, are offered in more than a dozen subjects (several in conjunction with Syracuse University[14]).

[15] Due in part to its rural setting, the school has established a learning track focused on environmental management and entrepreneurship.

Brown gymnasium, the Alumni Boathouse on Hatch Pond for rowing, the Anne H. Funnell cross-country trail, the hard court tennis courts, a weight-training facility, numerous athletics fields, and the adjacent Tom Fazio-designed Bulls Bridge Golf Club.

In the early 2000s, Headmaster Vadnais and the Board recognized that young athletes with professional aspirations not only fit the description in Father Sill's proposal,[36] but that many of them were likely to see high school as the final step in their education, as well.

[39] They include: Several notable athletes attended South Kent but graduated elsewhere; among them Nik Stauskas, Dion Waiters, Tremont Waters,[57] and Andrew Peeke.