Teach in a Joyfully Catholic, Classical Environment

Overview

Chesterton Academy of Orlando is a classical high school, rooted in the Catholic faith. We are seeking dynamic, mission-driven full-time teachers for the 2026–2027 academic year. Part-time opportunities may also be available.

We invite you to join a vibrant Catholic community where your faith is an asset and your love of learning helps shape young minds in truth, beauty, and goodness.

We are especially looking for a full time Latin/Literature teacher (with Latin or Literature as their primary specialty) or a full time Literature/Philosophy teacher (with Literature or Philosophy as their primary speciality). Above all, we seek a candidate who is a bona fide liberal artist, who can explain the difference between liberal and illiberal education in terms of Josef Pieper's Leisure the Basis of Culture and is familiar with the great books.

Prior teaching experience is a potential plus but not required for a successful candidate, so long as the applicant has been liberally educated themselves and is open to training in the pedagogy of St. John Bosco.

Faculty life

Beyond classroom teaching, faculty are integral to our school’s rich culture and spiritual life.

Teachers serve as advisors, mentors, and club leaders; participate actively in our House system; and attend important school events, concerts, plays, and sports activities.

Faculty also participate in retreats, prayer times, and other spiritual activities to foster a vibrant Catholic community.

Requirements

- Bachelor’s degree in History, Literature, Philosophy, Math, or a related Humanities field

- A passion for Catholic classical education

- Strong organizational, written, and verbal communication skills

- A practicing Catholic willing to take the Oath of Fidelity to the Magisterium.

- Commitment to the mission and values of Chesterton Academy of Orlando.

Preferred Qualifications

- Master’s degree in History, Literature, Philosophy, Math, or a related Humanities field

- 3-5 years of teaching experience (though not required)

- Ability and willingness to teach across multiple disciplines (considered a plus)

About Chesterton Academy

Chesterton Academy of Orlando is a classical high school, grounded in the Catholic faith, and one of the fastest growing private schools in Central Florida. We have an incredible campus located in Winter Park, FL. The school boasts a supportive community of families, business owners, donors, and other faithful Catholics in the area.

Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. As part of the Chesterton Schools Network, the school develops complete thinkers who learn to draw on faith and reason for the purpose of building a culture of life. Learn more at ChestertonOrlando.com.