Teacher (Latin, Literature, Or Philosophy)

Chesterton Academy of Orlando

Winter Park, FL

Job ID#:
12778174189
Posted:
March 13, 2026
Expires:
May 12, 2026
Category:
Secondary Education
Terms:
Full-Time Employee
Experience:
0-2 Years
Education:
Undergraduate Degree
Base Pay:
Salary
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Job Description

Given the explosive growth of our school, we are looking to hire multiple high school teachers.

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.

Each candidate must be a practicing Catholic and willing to take the Oath of Fidelity to the Magisterium. Candidates must demonstrate excellent organizational, written, and verbal communication skills, and possess a track record of contributing to the vision and mission of an apostolic and educational enterprise.

Interested candidates should apply below.

https://chestertonorlando.com/careers-teachers/
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About the Employer

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, with dozens of classrooms, a chapel, music room, and full gymnasium. The school boasts a supportive community of families, business owners, donors, and others faithful Catholics in the area.

Chesterton Academy offers a rigorous, integrated high school curriculum centered on the Incarnation of Jesus Christ. A member 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.