Top 10 most Expensive Private High Schools in America: tuition fess will shock youBy DreBoam / July 2, 2018 5. Middlesex School, Concord, Mass. Day student tuition: $38,710 Boarding student tuition: $48,390 Enrollment: 375 Endowment: $137 million Fact: Alumni include Gov. Bill Richardson and The Office‘s Steve Carell. Pages: 1 2 3 4 5 6 7 8 9 10