Grades PreK-12 200 students 11.4 students per teacher Baptist
Private schools in Chestertown, MD
7 schools within 12 miles. BOOST pays $1,200 to $4,750 in 2025-26, plus $3,000 for high school students.
Schools near Chestertown
Schools on the official BOOST list are first, then it goes by distance. No school pays to appear here or to move up.
Grades 1-8 54 students 3.8 students per teacher Nonsectarian Special education
Kent School
3 mi Grades PreK-8 120 students 4.6 students per teacher Nonsectarian
Grades PreK-K 4 students 2 students per teacher Nonsectarian Montessori
Grades PreK-12 149 students 10.3 students per teacher Christian (nondenominational)
The Gunston School
9 mi Grades 9-12 242 students 9.1 students per teacher Nonsectarian
Wye River Upper School
11 mi Grades 8-12 53 students 5.1 students per teacher Nonsectarian
On the state’s official list Other private schools
What Maryland pays, and what that leaves you
Maryland BOOST Scholarship Scholarship
$1,200 to $4,750 in 2025-26, plus $3,000 for high school students These are 2025-26 amounts. The advisory board sets new amounts each summer and had not posted 2026-27 figures in writing when we checked. The larger awards go to students coming from public school on free meals. Students receiving special education services got an extra award equal to their base award.
Figures read from each program’s official pages, 2026-09-21. Sources and how to apply
What would you pay?
Tuition and fees BOOST pays You pay per year Spread over 10 months
BOOST pays between $1,200 and $7,750 depending on your household. We start with the lower figure. Change it if you know yours. An award can never be more than the school actually charges. This is arithmetic, not a quote.
Keep looking
- All schools in Kent County
- All schools in Queen Anne's County
- Private schools in Kingsville (25 mi)
- Private schools in Bel Air (26 mi)
- Private schools in Annapolis (28 mi)
- Private schools in Severna Park (28 mi)
- Private schools in Glen Burnie (30 mi)
- Private schools in Easton (30 mi)
- Private schools in Elkton (31 mi)
- Private schools in Millersville (31 mi)
- Private schools in Baltimore (32 mi)
- Private schools in Towson (32 mi)
- How BOOST works
Get one email when applications open
Most programs open once a year, and several ran out of money or seats in 2026. Pick your state (you are looking at Chestertown) and we will email you the day the next window opens, with the official link. That is the only email you get.
One email per application window. No calls, no sharing your details.
Questions parents ask
How many private schools are there near Chestertown?
We count 7 within 12 miles of downtown Chestertown. Together they enrolled about 822 students in the last federal survey (2023-24). The largest is The Gunston School with 242 students.
Which Chestertown private schools take BOOST?
0 of the 7 schools on this page are on the state’s official BOOST list. They are marked with a green check and listed first. Schools marked “BOOST school” appear on the Maryland State Department of Education list of participating nonpublic schools for 2026-27, updated April 2026.
Will BOOST cover the whole tuition bill?
Sometimes, but do not count on it. BOOST pays $1,200 to $4,750 in 2025-26, plus $3,000 for high school students, and schools set their own prices. Ask each school for tuition plus fees, then use the calculator on this page to see what is left for you to pay.