High School with a Higher Purpose

Chesterton Academy of Annapolis is raising up joyful leaders and saints, educated in the classical tradition and the truths of the Catholic faith. Our rigorous, integrated curriculum unlocks student’s potential and prepares them to succeed in college and professional life, and to excel in service of family, of country, and of Christ our Lord.

Convenient Location

• The school is located in a prominent Annapolis location near Navy Stadium

• We are 1.4 miles from St. John Neumann Church off of Bestgate Road

By the Numbers

• 9th year of operation

• 19 faculty and staff members

• 77 students

• 33 families spanning 22 zip codes and 8 parishes

• Affordable tuition of $12,000 per student for the 2026-27 academic year; sibling discounts and tuition assistance available

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