32$304,000
3 bd · 2 ba · 1,232 sqft
7464 Shortall St, Chestertown, MD
Samantha A Grimes · Chesapeake Real Estate Associates, LLC
Homes for Sale in Chestertown, MD
Hide MapHomes for Sale in Chestertown, MD
24 of 59 Listings
32$304,000
3 bd · 2 ba · 1,232 sqft
7464 Shortall St, Chestertown, MD
Samantha A Grimes · Chesapeake Real Estate Associates, LLC
61$649,000
4 bd · 3 ba · 2,864 sqft
22400 Great Oak Landing Rd., Chestertown, MD
Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company
35$349,900
3 bd · 3 ba · 1,650 sqft
23208 Buck Neck Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
1$375,000
4 bd · 3 ba · 2,504 sqft
123 Trafford Dr, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
43$524,900
3 bd · 3 ba · 2,076 sqft
1003 Twin Ct, Chestertown, MD
Jody Baker · Cross Street Realtors LLC
18$295,000
1 bd · 1 ba · 0 sqft
117 N Water St #3B, Chestertown, MD
Michael ONeill · Coldwell Banker Chesapeake Real Estate Company
37$478,000
2 bd · 2 ba · 1,904 sqft
7982 Radcliffe Rd, Chestertown, MD
Abigail H Usilton · Doug Ashley Realtors, LLC
26$299,900
3 bd · 1 ba · 1,056 sqft
124 Wilton Rd, Chestertown, MD
Elizabeth Middleton Green · Doug Ashley Realtors, LLC
35$369,000
2 bd · 2 ba · 1,036 sqft
101 S College Ave, Chestertown, MD
Michele A Palmer · Doug Ashley Realtors, LLC
Price Reduced45$424,900
5 bd · 3 ba · 1,936 sqft
8630 Elm Rd, Chestertown, MD
Lawrence M. Lessin · Save 6, Incorporated
21$279,000
3 bd · 2 ba · 1,404 sqft
10540 Tonopah Rd, Chestertown, MD
Michele A Palmer · Doug Ashley Realtors, LLC
15$480,000
3 bd · 3 ba · 3,176 sqft
129 Trafford Dr, Chestertown, MD
Teresa A Queen · Elevated Real Estate Solutions
16$375,000
4 bd · 2 ba · 1,476 sqft
1010 Twin Ct, Chestertown, MD
Jason Dey · Kevin Dey Realty
17$1,195,000
2 bd · 1 ba · 806 sqft
302 S Mill St, Chestertown, MD
Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company
74$824,900
5 bd · 4 ba · 4,353 sqft
8999 Orchard Dr, Chestertown, MD
Terri L Kulp · Coldwell Banker Chesapeake Real Estate Company
10$259,900
3 bd · 2 ba · 1,280 sqft
115 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
34$325,000
4 bd · 2 ba · 2,198 sqft
200 Manor Ave, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
52$750,000
3 bd · 3 ba · 2,176 sqft
216 Birch Run Rd, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Price Reduced9$145,000
3 bd · 2 ba · 1,192 sqft
409 Calvert St, Chestertown, MD
Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC
43$885,000
5 bd · 4 ba · 2,639 sqft
7680 Country Club Ln, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
Price Reduced20$324,000
3 bd · 2 ba · 1,216 sqft
9126 Fairlee Rd, Chestertown, MD
Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC
Price Reduced21$179,900
2 bd · 1 ba · 1,232 sqft
21324 Persimmon Dr, Chestertown, MD
Taylor Leaverton · Benson & Mangold, LLC
34$325,000
3 bd · 1 ba · 1,000 sqft
896 Washington Ave, Chestertown, MD
Peter D Heller · Coldwell Banker Chesapeake Real Estate Company
68$799,000
3 bd · 3 ba · 2,857 sqft
7828 Country Club Ln, Chestertown, MD
Sarah E. King · Cross Street Realtors LLC
Bright MLSSource: HJN community data
August 2026 · This period is still settling
Selling at 100.0% of asking price
Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026