New23$312,500
3 bd · 2 ba · 1,080 sqft
8820 Cumberland St, Chestertown, MD
Frederick Golding · RE/MAX Advantage Realty
3 Bedroom Homes in Chestertown, MD
Show Map3 Bedroom Homes in Chestertown, MD
24 of 32 Listings
New23$312,500
3 bd · 2 ba · 1,080 sqft
8820 Cumberland St, Chestertown, MD
Frederick Golding · RE/MAX Advantage Realty
24$289,000
3 bd · 2 ba · 1,056 sqft
8732 Elm Rd, Chestertown, MD
Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company
16$259,900
3 bd · 3 ba · 1,280 sqft
103 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
23$229,000
3 bd · 1 ba · 936 sqft
7415 Wilkins Ln, Chestertown, MD
Retha J Arrabal · Doug Ashley Realtors, LLC
Price Reduced30$285,000
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 Reduced48$499,900
3 bd · 3 ba · 2,076 sqft
1003 Twin Ct, Chestertown, MD
Jody Baker · Cross Street Realtors LLC
Price Reduced34$259,000
3 bd · 2 ba · 1,140 sqft
115 Chester Arms Dr, Chestertown, MD
Jarnell Preston Foster · Samson Properties
23$299,900
3 bd · 1 ba · 1,056 sqft
124 Wilton Rd, Chestertown, MD
Elizabeth Middleton Green · Doug Ashley Realtors, LLC
Price Reduced21$269,000
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
10$259,900
3 bd · 2 ba · 1,280 sqft
115 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
52$750,000
3 bd · 3 ba · 2,176 sqft
216 Birch Run Rd, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Price Reduced20$314,000
3 bd · 2 ba · 1,216 sqft
9126 Fairlee Rd, Chestertown, MD
Mikeshia D Lindsey · Chesapeake Real Estate Associates, 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
10$264,900
3 bd · 2 ba · 0 sqft
121 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced26$239,900
3 bd · 2 ba · 1,280 sqft
104 Conley Dr, Chestertown, MD
Heather Kooser · Cummings & Co. Realtors
Price Reduced26$275,000
3 bd · 3 ba · 1,900 sqft
104 Acorn Dr, Chestertown, MD
Sarah E. King · Cross Street Realtors LLC
Price Reduced29$275,000
3 bd · 1 ba · 1,248 sqft
956 Washington Ave, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
Price Reduced10$315,000
3 bd · 2 ba · 1,232 sqft
8706 Elm Rd, Chestertown, MD
Andrew Hanson Meikle · Doug Ashley Realtors, LLC
31$898,000
3 bd · 4 ba · 2,172 sqft
226 S Water St, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
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
46$685,000
3 bd · 3 ba · 3,000 sqft
117 Water St N #1a, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Bright MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 100.0% of asking price
Sales here are closing essentially at asking. MLS · 16 sales · as of Sep 29, 2026