The house system is as old as Charlemont High School. In the early years Charlemont had four houses, namely Headley, Quarrie, Holding and Delanpenah. The houses were renamed Drummond, Grant, Whitehead and Stephenson, all named after persons who have served the school at some point with distinction. Much later Powell House, in honour of an outstanding athlete and past student Asafa Powell, was added to the list of houses.

Sporting competitions are held in the major sports and points are awarded to winning teams. The winning house champion boy and girl are selected in this format. All sporting activities are supervised. Permission to participate in these activities must be signed and returned to the school before a child is allowed to do so. Students who are not insured will not be allowed to participate in any extracurricular sporting activities.