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The Best Private Schools in Chester, Maryland

Discover 3 exceptional private schools in Chester. Find the perfect educational environment for your child with our comprehensive reviews and ratings.

3
Private Schools
4.7
Average Rating
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Total Students
3
School Types

School Overview

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Religious Schools
3
Secular Schools
3
Different Types

Top-Rated Private Schools

The Gunston School

Independent College Preparatory School

4.8

The Gunston School is a highly regarded independent college preparatory day school serving students in grades 9-12. Located just 15 minutes from Chester, Gunston offers a rigorous academic program with small class sizes and personalized attention. The school features a 35-acre waterfront campus on the Corsica River, providing exceptional environmental science and marine biology opportunities. Gunston's curriculum emphasizes critical thinking, ethical leadership, and global citizenship, with strong programs in STEM, humanities, and the arts. The school boasts a 100% college acceptance rate and offers numerous advanced placement courses and college counseling services.

911 Gunston Road, Centreville, MD 21617, Chester, Maryland MD 21617
Grades: K-12
Founded 1911

Programs:

College Preparatory CurriculumSTEM ProgramEnvironmental Science+1 more

The Key School

Independent School

4.7

The Key School is a prestigious independent school located approximately 30 minutes from Chester, serving students from pre-kindergarten through grade 12. As an International Baccalaureate World School, Key offers the IB Diploma Programme alongside a comprehensive college preparatory curriculum. The school features state-of-the-art facilities including science labs, performing arts centers, and athletic complexes. Key School emphasizes experiential learning, critical thinking, and community engagement, with strong programs in mathematics, sciences, humanities, and the arts. The school maintains small class sizes and has an excellent college placement record.

534 Hillsmere Drive, Annapolis, MD 21403, Chester, Maryland MD 21403
Grades: K-12
Founded 1958

Programs:

International BaccalaureateSTEMArts+1 more

Saints Peter and Paul Catholic School

Catholic Diocese of Wilmington

4.6

Saints Peter and Paul Catholic School serves students from pre-kindergarten through 8th grade and is located approximately 25 minutes from Chester. The school provides a faith-based education integrated with a rigorous academic curriculum. SSPP features modern classrooms, science labs, technology centers, and athletic facilities. The school offers a comprehensive STEM program, foreign language instruction, fine arts, and competitive athletics. With small class sizes and dedicated faculty, the school emphasizes character development, academic excellence, and service to the community. The school prepares students for success in high school and beyond through its challenging curriculum and supportive environment.

9059 Ocean Gateway, Easton, MD 21601, Chester, Maryland MD 21601
Grades: K-12
Founded 1970

Programs:

Catholic EducationSTEMFine Arts+1 more

Frequently Asked Questions

Common questions about private schools in Chester, Maryland

What are the primary private school options available for families in Chester, MD, and what educational philosophies do they represent?

Chester, MD, and the broader Kent Island/Annapolis region offer a few distinct private school options. The Gunston School, located in Centreville just a short drive from Chester, is a prestigious, co-educational, college-preparatory day school for grades 9-12 with a strong emphasis on environmental stewardship due to its waterfront campus. The Key School in Annapolis offers a progressive, independent education from pre-K through 12th grade, known for its interdisciplinary curriculum. For families seeking a faith-based education, Saints Peter and Paul Catholic School in Easton provides a PK-8 program rooted in Catholic values. These schools represent the core independent and parochial options accessible to Chester residents.

How does tuition for private schools near Chester, MD, compare to the state average, and what financial aid options are typically available?

Tuition for private schools in the Chester area is generally at or above the Maryland state average for private education, reflecting the region's cost of living and the schools' reputations. For the 2024-2025 academic year, expect ranges of approximately $25,000-$35,000+ for upper schools like Gunston and Key, while Saints Peter and Paul Catholic School is typically lower, often in the $8,000-$12,000 range. All these schools offer need-based financial aid, and Maryland residents should also explore the Broadening Options and Opportunities for Students Today (BOOST) Scholarship Program, a state-funded initiative that provides K-12 scholarships for eligible students to attend nonpublic schools.

What unique academic or extracurricular programs are offered by private schools accessible from Chester, MD, that leverage the local Chesapeake Bay environment?

Private schools in this region uniquely integrate the Chesapeake Bay into their curricula. The Gunston School's signature "Chesapeake Bay Studies" program is a prime example, where students engage in hands-on marine biology, environmental science, and sustainability projects directly on the Corsica River. The Key School also emphasizes experiential learning with its waterfront location and outdoor education. This localized focus provides students with unparalleled opportunities in environmental science, sailing, and ecological stewardship that are distinctive to schools in the Chester and greater Eastern Shore area.

What is the typical enrollment timeline and process for private schools like The Gunston School for a Chester, MD, family, and are there specific considerations for upper school entry?

The enrollment process for competitive schools like The Gunston School begins early, often in the fall prior to the desired enrollment year (e.g., September/October for entry the following August). The process typically includes submitting an application, student transcripts, teacher recommendations, standardized test scores (like the SSAT or ISEE), and a mandatory campus interview/visit. For Chester families, it's crucial to plan for potential travel to Centreville for visits and interviews. Admissions decisions for upper schools are usually released in March. Given the limited seats, especially for incoming 9th graders, starting the process 12-18 months in advance is highly advised.

For a Chester, MD resident, what are the key factors in choosing between the local public schools (Queen Anne's County) and the available private school options?

The decision often hinges on several location-specific factors. Queen Anne's County Public Schools are well-regarded, so families may consider private options for more specialized college-prep rigor (Gunston, Key), a specific religious education (Saints Peter and Paul), or smaller class sizes and individualized attention. The private schools offer distinct educational philosophies (progressive at Key, traditional college-prep with an environmental focus at Gunston) that may align better with a child's learning style. Practical considerations include the daily commute to schools outside Chester (Annapolis or Centreville), the significant financial investment, and the desire for a particular community or network. Many Chester families value the private schools' ability to deeply connect academic learning with the unique cultural and environmental context of the Eastern Shore.

Private Education Insights

Discover Top-Rated Private Schools in Chester, MD: A Parent's Guide

When you begin searching for "private schools near me" in Chester, Maryland, you are embarking on a journey to find an educational environment that aligns with your family's values and your child's unique potential. Chester, nestled on Maryland's scenic Eastern Shore, offers a distinctive blend of close-knit community and access to exceptional private education, each with its own character and approach. This search is about more than proximity; it's about finding the right fit within the fabric of our local area, where the Chesapeake Bay influences both lifestyle and learning.

For families in Chester, the concept of "private schools near me" often translates to institutions that leverage our unique setting while providing rigorous academics. The Gunston School, for instance, is a premier independent day and boarding school right here in our community, known for its waterfront campus that integrates environmental science and leadership directly into its curriculum. This is a school where the local ecosystem becomes a living classroom, offering an educational experience deeply connected to the Chester River and the Bay. Meanwhile, a short drive over the bridge brings you to The Key School in Annapolis, which emphasizes experiential learning and intellectual curiosity, appealing to Chester families seeking a progressive, student-centered approach within a reasonable commute.

For those prioritizing a faith-based education intertwined with strong academics, Saints Peter and Paul Catholic School in Easton provides a structured, values-oriented environment. It represents a cornerstone for many local Catholic families, fostering a sense of moral development and community service. The search for "private schools near me" in our area must also consider practical logistics. Chester’s location means families often look at schools in a radius that includes not just Queen Anne’s County, but also Talbot County and Anne Arundel County. This requires thoughtful consideration of daily commutes across the Kent Narrows or the Chesapeake Bay Bridge, factoring in not just distance but also seasonal traffic patterns that are part of life on the Shore.

As you evaluate options, we encourage you to look beyond the brochures and websites. The true measure of a school’s fit often reveals itself during a campus visit. Attend an open house, observe classroom interactions, and speak with current parents. Ask specific questions about how the school engages with the local Chester and Eastern Shore community through partnerships, field trips, and service projects. Does the school’s philosophy resonate with how you are raising your child? Does it offer the academic challenges and supportive environment they need to thrive? Your search for "private schools near me" is a significant decision, but Chester is fortunate to be surrounded by several outstanding choices, each capable of providing a transformative education. Taking the time to explore these local gems will help you find a school where your child will not only learn but truly belong.

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