New23$312,500
3 bd · 2 ba · 1,080 sqft
8820 Cumberland St, Chestertown, MD
Frederick Golding · RE/MAX Advantage Realty
Homes Under $600K in Chestertown, MD
Hide MapHomes Under $600K in Chestertown, MD
24 of 38 Listings
New23$312,500
3 bd · 2 ba · 1,080 sqft
8820 Cumberland St, Chestertown, MD
Frederick Golding · RE/MAX Advantage Realty
22$329,900
2 bd · 2 ba · 1,440 sqft
22974 Bay Shore Rd, Chestertown, MD
Mae Nordhoff · Benson & Mangold, LLC
51$489,000
2 bd · 2 ba · 1,098 sqft
105 N Water St #3, Chestertown, MD
Lisa P Raffetto · Coldwell Banker Chesapeake Real Estate Company
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 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 Reduced34$259,000
3 bd · 2 ba · 1,140 sqft
115 Chester Arms Dr, Chestertown, MD
Jarnell Preston Foster · Samson Properties
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 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
Price Reduced25$349,900
4 bd · 2 ba · 1,476 sqft
1010 Twin Ct, Chestertown, MD
Jason Dey · Kevin Dey Realty
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
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
Homes Under $600K in Chestertown, MD: 38 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Single Family Residence | 21 | 55.3% |
| Townhouse | 5 | 13.2% |
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