For the 2025-26 school year, there are 4 private schools serving 391 students in Chestertown, MD (there are 2 public schools, serving 711 public students). 35% of all K-12 students in Chestertown, MD are educated in private schools (compared to the MD state average of 14%).
The average acceptance rate is 73%, which is lower than the Maryland private school average acceptance rate of 78%.
50% of private schools in Chestertown, MD are religiously affiliated (most commonly Baptist and Seventh Day Adventist).
Private Schools in Chestertown, MD (2025-26)
School
Location
Quick Facts
Chester River Adventist School![Chester River Adventist School Photo Chester River Adventist School Photo]()

(Seventh Day Adventist)
305 N Kent St
Chestertown, MD 21620
(410) 778-2193
Chestertown, MD 21620
(410) 778-2193
Gr: 1-8 | 5 students Extracurrculars: 3 Tuition listed
401 Morgnec Rd
Chestertown, MD 21620
(410) 778-5855
Chestertown, MD 21620
(410) 778-5855
Gr: PK-12 | 170 students Avg. class size: 14 students Sports: 4 Tuition listed
6788 Wilkins Ln
Chestertown, MD 21620
(410) 778-4100
Chestertown, MD 21620
(410) 778-4100
Gr: PK-8 | 159 students Avg. class size: 15 students Sports: 4 | Extracurrculars: 6 Tuition listed
201 Talbot Blvd
Chestertown, MD 21620
(410) 778-8150
Chestertown, MD 21620
(410) 778-8150
Gr: K-8 | 57 students Avg. class size: 5 students Sports: 6 Tuition & acceptance rate listed
Frequently Asked Questions
How many private schools are located in Chestertown, MD?
4 private schools are located in Chestertown, MD.
What percentage of students in Chestertown go to private school?
35% of all K-12 students in Chestertown are educated in private schools (compared to the MD state average of 14%).
What percentage of private schools are religiously affiliated in Chestertown?
50% of private schools in Chestertown are religiously affiliated (most commonly Baptist and Seventh Day Adventist).
Which private schools in Chestertown are often viewed compared to one another?
Popular comparisons of private schools in Chestertown include: Radcliffe Creek School vs. Chestertown Christian Academy, Chestertown Christian Academy vs. Radcliffe Creek School
Recent Articles

Transferring from Public to Private School Mid-Year: What to Expect
Considering a mid-year transfer from public to private school? Learn what to expect with admissions, academic placement, social adjustment, and financial aid to ensure a smooth transition.

A Guide to Day vs. Boarding School: Which Is Right for Your Family
Discover the key differences between day and boarding schools to determine the best fit for your child. Explore benefits, costs, lifestyle factors, and questions to help guide your family’s decision.

The A to Z of Private Schools 2025
Explore the A to Z of private schools in 2025—from admissions to tuition—offering parents and educators clear insights into today’s options.