Website Chesterton Academy of Orlando Winter Park, FL, Florida

We are currently looking for a LITERATURE teacher (9th-12th grades). An ability to also teach introductory LATIN would be strongly valued.

We prefer someone with a bachelor’s or master’s degree in Literature, History, or a related Humanities field.

Three to five years of teaching experience is also preferred, though we will consider candidates without extensive experience.

The 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.

In addition to their teaching responsibilities, faculty at Chesterton Academy participate in the House system, which is designed to promote character and virtue, and to help students grow in holiness. Faculty members are required to assist in the House system and participate in spiritual activities in the school, including retreats and times of prayer.

Interested candidates should apply here:

Chesterton Academy of Orlando is a classical high school, grounded in the Catholic faith. We have an incredible campus located in Winter Park, FL, with 27 classrooms, dedicated spaces for Art, Music, Science, and Reading, and a 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

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