18$175,000
3 bd · 1 ba · 1,360 sqft
7545 Quaker Neck Rd, Chestertown, MD
Byron K. Brooks · Thurston Wyatt Real Estate, LLC
3 Bedroom Homes in Chestertown, MD
Hide Map3 Bedroom Homes in Chestertown, MD
24 of 34 Listings
18$175,000
3 bd · 1 ba · 1,360 sqft
7545 Quaker Neck Rd, Chestertown, MD
Byron K. Brooks · Thurston Wyatt Real Estate, LLC
28$365,000
3 bd · 3 ba · 2,294 sqft
24607 Chestertown Rd, Chestertown, MD
William Sutton · Coldwell Banker Chesapeake Real Estate Company
50$519,900
3 bd · 3 ba · 2,475 sqft
7655 James Ln, Chestertown, MD
Ryan Michael Fitzwater · RE/MAX Advantage Realty
51$525,000
3 bd · 3 ba · 1,833 sqft
8901 S Bayview Dr, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
Price Reduced24$281,500
3 bd · 2 ba · 1,080 sqft
8820 Cumberland St, Chestertown, MD
Frederick A Golding · RE/MAX Advantage Realty
39$495,000
3 bd · 3 ba · 1,656 sqft
10 Cedar Chase Ct, Chestertown, MD
Sarah E. King · Cross Street Realtors LLC
53$679,900
3 bd · 4 ba · 3,228 sqft
8986 Orchard Dr, Chestertown, MD
Taylor Leaverton · Benson & Mangold, 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
16$259,900
3 bd · 3 ba · 1,280 sqft
103 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced23$222,000
3 bd · 1 ba · 936 sqft
7415 Wilkins Ln, Chestertown, MD
Retha J Arrabal · Doug Ashley Realtors, LLC
Price Reduced25$305,000
3 bd · 1 ba · 1,008 sqft
24775 Langford Rd, Chestertown, MD
Joseph A Zang III · RE/MAX Chesapeake
Price Reduced30$275,000
3 bd · 1 ba · 960 sqft
104 Lincoln Dr, Chestertown, MD
Crystal M Smith · RE/MAX Executive
Price Reduced34$259,000
3 bd · 2 ba · 1,140 sqft
115 Chester Arms Dr, Chestertown, MD
Jarnell Preston Foster · Samson Properties
Price Reduced21$267,000
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
Price Reduced52$730,000
3 bd · 3 ba · 2,176 sqft
216 Birch Run Rd, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Price Reduced20$313,500
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
31$898,000
3 bd · 4 ba · 2,172 sqft
226 S Water St, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
3 Bedroom Homes in Chestertown, MD: 34 active listings as of .
| Property type | Listings | Share |
|---|---|---|
| Single Family Residence | 15 | 44.1% |
| Townhouse | 6 | 17.6% |
Bright MLSSource: HJN community data
October 2026 · This period is still settling