Catholic School CompassTrue north for Catholic families.
Aerial view of Chesterton Academy of Orlando
Aerial imagery: U.S. Geological Survey (public domain). USGS

Catholic high school

Chesterton Academy of Orlando

  • LocationWinter Park, FL
  • Type and sizeIndependent Catholic school · Grades 9–12 · 53 students
Official website

Chesterton Academy of Orlando is an independent, parent-led classical high school in Winter Park for grades 9 to 12. The school says it is grounded in the Catholic faith and is not associated with the Diocese of Orlando. It states that all students take four years of Catholic theology and that each day begins with prayer, and two priests are listed as its chaplains.

Catholic churches nearby

Map of Chesterton Academy of Orlando, its Catholic center and nearby Catholic churches1 mi2 mi3 miSaints Peter and Paul Catholic Church: 1.7 mi1Saint Margaret Mary Catholic Church: 2.5 mi2Chesterton Academy of Orlando campus chapel: 0.1 miChesterton Academy of Orlando (campus)N1 mi
CampusCatholic centerCatholic church (numbered below)Open a street map ›
  1. Saints Peter and Paul Catholic Church — 1.7 mi
  2. Saint Margaret Mary Catholic Church — 2.5 mi · 526 North Park Avenue, Winter Park

Within 3 miles, as mapped by OpenStreetMap contributors. The map may be incomplete. Confirm with the parish or diocese.

Faith scorecard

Each line is one thing we looked for. A check means yes, a half means partly, a dash means no. “Not enough information” means official sources did not say.

N/ASacramental life: Not enough information. Official sources do not cover enough of this to grade it yet.

Sacramental life

Not enough information: official sources cover less than 60% of this area.

  • Partly: the school meets some of this item and earns part of the points.
    All-school or class Masses during the school yearA few times a year (The FAQ says all students are required to take part in school events, including Mass.)
    Sources (1)
    1. Frequently Asked Questions - Chesterton Academy of Orlandochestertonorlando.com/faq · verified Oct. 13, 2026
      “We do require four years of Catholic theology, the curriculum is infused with Catholic thought, and all students are required to participate in school events, including Mass, retreats, and other prayer services.”
      The school requires four years of Catholic theology and requires students to attend school events including Mass.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Daily Mass available to students on campusNot enough information: not found in official sources.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Confession offered to students during the school yearNot enough information: not found in official sources.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Eucharistic adoration offeredNot enough information: not found in official sources.
  • Yes: the school meets this item and earns its full points.
    Priest chaplain serving the schoolYes (The current faculty page lists two priests as the school's chaplains.)
    Sources (1)
    1. Faculty and Staff - Chesterton Academy of Orlandochestertonorlando.com/faculty · verified Oct. 13, 2026
      “Fr. Josh Swallows Chaplain”
      Fr. Josh Swallows is listed as a chaplain of the school.
      “Fr. Kenneth Bolin CHAPLAIN”
      Fr. Kenneth Bolin is listed as a chaplain of the school.
ATheology and curriculum: Strong (grade A): 85 to 100 points out of 100 on what official sources document. Grades need sources for at least 60% of the checklist.

Theology and curriculum

100 of 100 points on what we could document.

  • Yes: the school meets this item and earns its full points.
    Years of theology or religion requiredFour years (The FAQ states the school requires four years of Catholic theology; it is taken in every grade.)
    Sources (1)
    1. Frequently Asked Questions - Chesterton Academy of Orlandochestertonorlando.com/faq · verified Oct. 13, 2026
      “We do require four years of Catholic theology, the curriculum is infused with Catholic thought, and all students are required to participate in school events, including Mass, retreats, and other prayer services.”
      The school requires four years of Catholic theology and requires students to attend school events including Mass.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Theology courses follow the USCCB Curriculum FrameworkNot enough information: not found in official sources.
  • Yes: the school meets this item and earns its full points.
    Philosophy, apologetics, or ethics course offeredYes (The curriculum page describes a philosophy strand studying Plato, Aristotle and Thomas Aquinas.)
    Sources (1)
    1. Curriculum - Chesterton Academy of Orlandochestertonorlando.com/curriculum · verified Oct. 13, 2026
      “We study the development of philosophy from its classical roots focusing on Plato and Aristotle, its dramatic encounter with the early Church, its christening by St. Thomas Aquinas, and its deterioration in the modern era.”
      The curriculum includes a philosophy strand.
  • Yes: the school meets this item and earns its full points.
    Faith integrated across the curriculum (stated in the program of studies or mission)Yes (The school's model page says the Incarnation is the central event explored in all classes and across the disciplines.)
    Sources (1)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “Catholicism is central to our mission. All classes point to the Incarnation as the central event in human history, so students won't just learn about their faith in one class, but across the disciplines.”
      The school says faith is taught across all classes, not only in theology.
ACampus culture: Strong (grade A): 85 to 100 points out of 100 on what official sources document. Grades need sources for at least 60% of the checklist.

Campus culture

85 of 100 points on what we could document.

  • Partly: the school meets some of this item and earns part of the points.
    RetreatsRetreats for some grades (The school says it offers regular retreats; this is recorded as retreats offered as an opportunity.)
    Sources (1)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “We begin each day with the Liturgy of the Hours and each class with prayer. We also offer regular retreats, annual pilgrimages, wholesome activities themed around the liturgical year, and sacred art and crucifixes adorning the classrooms.”
      The school begins each day with prayer and offers regular retreats.
  • Yes: the school meets this item and earns its full points.
    Campus ministry staffTwo or more (Two priests are listed as the school's chaplains on the current faculty page. Both are also parish pastors; the count rests on the chaplain listing alone.)
    Sources (1)
    1. Faculty and Staff - Chesterton Academy of Orlandochestertonorlando.com/faculty · verified Oct. 13, 2026
      “Fr. Josh Swallows Chaplain”
      Fr. Josh Swallows is listed as a chaplain of the school.
      “Fr. Kenneth Bolin CHAPLAIN”
      Fr. Kenneth Bolin is listed as a chaplain of the school.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Faith-based student groups or clubsNot enough information: not found in official sources.
  • Yes: the school meets this item and earns its full points.
    Daily prayer and liturgical life built into the school dayYes (The school says it begins each day with the Liturgy of the Hours and each class with prayer.)
    Sources (1)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “We begin each day with the Liturgy of the Hours and each class with prayer. We also offer regular retreats, annual pilgrimages, wholesome activities themed around the liturgical year, and sacred art and crucifixes adorning the classrooms.”
      The school begins each day with prayer and offers regular retreats.
N/AService and Catholic social teaching: Not enough information. Official sources do not cover enough of this to grade it yet.

Service and Catholic social teaching

Not enough information: official sources cover less than 60% of this area.

  • Yes: the school meets this item and earns its full points.
    Required service hours40 or more hours over four years (The school requires at least 10 volunteer hours per semester. Across eight semesters that is 80 hours.)
    Sources (1)
    1. Parent Information - Chesterton Academy of Orlandochestertonorlando.com/parents · verified Oct. 13, 2026
      “Chesterton Academy requires that all students volunteer at least 10 hours of their time per semester, to give back to the community.”
      Students must complete at least 10 volunteer hours per semester.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Catholic social teaching taught in theology coursesNot enough information: not found in official sources.
  • Yes: the school meets this item and earns its full points.
    Pro-life engagement (club, March for Life, or similar)Yes (The school lists a March for Life trip among its pilgrimages.)
    Sources (1)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “In addition to the March for Life and local pilgrimages, Chesterton Academy students travel to Rome and Assisi (Italy) as upperclassmen”
      The school takes students to the March for Life and local pilgrimages.
  • Not enough information: official sources do not document this, so it is left out of the grade rather than counted as a no.
    Justice and solidarity programs (immersions, service trips, justice clubs)Not enough information: not found in official sources.

Grades come from the documented indicators under the published rubric. “Not enough information” does not mean the school lacks it.

Strengths

  • The school requires four years of Catholic theology.
    Sources (1)
    1. Frequently Asked Questions - Chesterton Academy of Orlandochestertonorlando.com/faq · verified Oct. 13, 2026
      “We do require four years of Catholic theology, the curriculum is infused with Catholic thought, and all students are required to participate in school events, including Mass, retreats, and other prayer services.”
      The school requires four years of Catholic theology and requires students to attend school events including Mass.
  • The school says faith is integrated across all classes.
    Sources (1)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “Catholicism is central to our mission. All classes point to the Incarnation as the central event in human history, so students won't just learn about their faith in one class, but across the disciplines.”
      The school says faith is taught across all classes, not only in theology.
  • Each day begins with prayer, and students must complete 10 volunteer hours per semester.
    Sources (2)
    1. Our Model - Chesterton Academy of Orlandochestertonorlando.com/model · verified Oct. 13, 2026
      “We begin each day with the Liturgy of the Hours and each class with prayer. We also offer regular retreats, annual pilgrimages, wholesome activities themed around the liturgical year, and sacred art and crucifixes adorning the classrooms.”
      The school begins each day with prayer and offers regular retreats.
    2. Parent Information - Chesterton Academy of Orlandochestertonorlando.com/parents · verified Oct. 13, 2026
      “Chesterton Academy requires that all students volunteer at least 10 hours of their time per semester, to give back to the community.”
      Students must complete at least 10 volunteer hours per semester.

Concerns

  • The school is not associated with the Diocese of Orlando.
    Sources (1)
    1. Frequently Asked Questions - Chesterton Academy of Orlandochestertonorlando.com/faq · verified Oct. 13, 2026
      “No. This high school is not associated with the Diocese of Orlando. It is an independent, parent-led high school grounded in the Catholic faith.”
      The school describes itself as independent and not associated with the Diocese of Orlando.

Know something we missed? Suggest a correction.

Campus ministry home

Chesterton Academy of Orlando campus chapel

  • Address: 2025 State Road 436, Winter Park, FL 32792
  • Location: On campus
  • Facilities: chapel

View on map ↗

Source: chestertonorlando.com, verified Oct. 13, 2026, chestertonorlando.com, verified Oct. 13, 2026

Catholic clubs and student life

5 groups and regular activities · 1 on campus, 2 off campus, 2 location not published

Other 1

  • Senior pilgrimage to ItalyOff campus
    Each year during the Easter season (senior class)
    Seniors travel to Italy as a school pilgrimage, which the school says includes Papal events and sacred sites.
    chestertonorlando.com

Service 2

  • March for Life and local pilgrimagesOff campus
    The school lists the March for Life and local pilgrimages among its pilgrimage opportunities.
    chestertonorlando.com
  • Apostolic Hours (student volunteering)
    At least 10 hours per semester
    Required volunteer hours that students log and submit each semester.
    chestertonorlando.com

Clubs and groups 1

  • House systemOn campus
    Students are sorted into four Houses led by student prefects with faculty advisors. Houses build community through service projects, competitions, celebrations and prayer.
    chestertonorlando.com

Retreats 1

Everything listed is published by the school, its campus ministry, or the parish. Ask the campus minister what’s happening this semester.

Campus ministry

Sources (3)
  1. Faculty and Staff - Chesterton Academy of Orlandochestertonorlando.com/faculty · verified Oct. 13, 2026
    “Fr. Josh Swallows Chaplain”
    Fr. Josh Swallows is listed as a chaplain of the school.
    “Fr. Kenneth Bolin CHAPLAIN”
    Fr. Kenneth Bolin is listed as a chaplain of the school.
  2. Location - Chesterton Academy of Orlandochestertonorlando.com/location · verified Oct. 13, 2026
    “2025 State Road 436, Winter Park, FL 32792”
    The school's campus address is 2025 State Road 436, Winter Park, FL 32792.
  3. Frequently Asked Questions - Chesterton Academy of Orlandochestertonorlando.com/faq · verified Oct. 13, 2026
    “The campus includes several classrooms, a gymnasium, chapel, and dedicated spaces for science, art, and music.”
    The campus has a chapel.

Reach out

Contact details for Jo Guzman (Director of Mission) and the campus ministry are available to signed-in users.

Sign in Create a free account

We keep campus ministers’ emails behind sign-in to protect them from spam.

My rating and notes

Sign in or create a free account to rate this school privately, keep notes, and save it to your list.

Academic Excellence

N/AAcademic Excellence: Not enough information. Official sources do not cover enough of this to grade it yet.
Not enough information
Federal data covers too few of the measures to score this school.

Each measure counts for the share shown.

  • Graduates going to four-year colleges 75% of scoreThis measure counts for 75% of the Academic Excellence score.Not reported
  • Students per teacher 25% of scoreThis measure counts for 25% of the Academic Excellence score.11.5 to 1

Bars show points on each measure’s scale. How Academic Excellence is computed. Federal data on private high schools is limited to these two measures.

Source: NCES Private School Survey (2023–24 school year)

School facts

TypeIndependent Catholic school
DioceseDiocese of Orlando, FL
Grades9–12
Students (all grades)53
Students in grades 9–1253
Coed or single-sexCoed
Student–teacher ratio11.5 to 1
Graduates going to 4-year colleges—
SettingSuburb

Source: NCES Private School Survey 23-24 public-use file (school year 2023–24). The college-going rate and student–teacher ratio feed Academic Excellence; nothing here changes the faith grades.

Local Church

Diocese of Orlando

The Most Reverend John Noonan, Bishop of Orlando

Formal address: “Your Excellency”

Source: orlandodiocese.org, orlandodiocese.org, verified Oct. 7, 2026.

About this school’s data

Questions families ask

Is Chesterton Academy of Orlando a Catholic high school?
Yes. Chesterton Academy of Orlando is a Catholic high school in the Diocese of Orlando.

Reviews

Personal experiences from signed-in readers. Reviews are moderated automatically and never change a school’s grades.

No reviews yet.

Sign in to write a review.

More in Florida · Florida rankings