22$329,900
2 bd · 2 ba · 1,440 sqft
22974 Bay Shore Rd, Chestertown, MD
Mae Nordhoff · Benson & Mangold, LLC
Single-Family Homes in Chestertown, MD
Hide MapSingle-Family Homes in Chestertown, MD
24 of 27 Listings
22$329,900
2 bd · 2 ba · 1,440 sqft
22974 Bay Shore Rd, Chestertown, MD
Mae Nordhoff · Benson & Mangold, LLC
56$2,895,000
5 bd · 4 ba · 5,938 sqft
6324 Quaker Neck Rd, Chestertown, MD
John Boniface · Cross Street Realtors LLC
82$1,295,000
4 bd · 4 ba · 3,383 sqft
8276 Broad Neck Rd, Chestertown, MD
Hayley A Norris · Select Land & Homes, LLC
24$289,000
3 bd · 2 ba · 1,056 sqft
8732 Elm Rd, Chestertown, MD
Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company
23$229,000
3 bd · 1 ba · 936 sqft
7415 Wilkins Ln, Chestertown, MD
Retha J Arrabal · Doug Ashley Realtors, LLC
Price Reduced30$295,000
3 bd · 1 ba · 960 sqft
104 Lincoln Dr, Chestertown, MD
Crystal M Smith · RE/MAX Executive
Price Reduced36$335,000
3 bd · 2 ba · 1,398 sqft
217 Edmore Rd, Chestertown, MD
Michele A Palmer · Doug Ashley Realtors, LLC
35$349,900
3 bd · 3 ba · 1,650 sqft
23208 Buck Neck Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced45$370,000
4 bd · 3 ba · 2,504 sqft
123 Trafford Dr, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
Price Reduced48$499,900
3 bd · 3 ba · 2,076 sqft
1003 Twin Ct, Chestertown, MD
Jody Baker · Cross Street Realtors LLC
Price Reduced37$399,000
2 bd · 2 ba · 1,904 sqft
7982 Radcliffe Rd, Chestertown, MD
Abigail H Usilton · Doug Ashley Realtors, LLC
23$299,900
3 bd · 1 ba · 1,056 sqft
124 Wilton Rd, Chestertown, MD
Elizabeth Middleton Green · Doug Ashley Realtors, LLC
Price Reduced35$359,000
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
Price Reduced25$365,000
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
300 And 302 S Mill St, Chestertown, MD
Joseph S. Ciganek · Coldwell Banker Chesapeake Real Estate Company
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 Reduced43$825,000
5 bd · 4 ba · 2,639 sqft
7680 Country Club Ln, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
Price Reduced20$314,000
3 bd · 2 ba · 1,216 sqft
9126 Fairlee Rd, Chestertown, MD
Mikeshia D Lindsey · Chesapeake Real Estate Associates, LLC
Price Reduced54$429,500
4 bd · 3 ba · 2,160 sqft
10781 Fermoy Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced50$1,375,000
4 bd · 5 ba · 4,257 sqft
22470 Fairgale Farm Ln, Chestertown, MD
Ashton M Kelley · Gunther-McClary Real Estate
Price Reduced10$315,000
3 bd · 2 ba · 1,232 sqft
8706 Elm Rd, Chestertown, MD
Andrew Hanson Meikle · Doug Ashley Realtors, LLC
Price Reduced92$829,000
3 bd · 4 ba · 2,472 sqft
106 Queen St S, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, 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