Price Reduced45$370,000
4 bd · 3 ba · 2,504 sqft
123 Trafford Dr, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
Homes for Sale in Chestertown, MD
Hide MapHomes for Sale in Chestertown, MD
24 of 63 Listings
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 Reduced34$259,000
3 bd · 2 ba · 1,140 sqft
115 Chester Arms Dr, Chestertown, MD
Jarnell Preston Foster · Samson Properties
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 Reduced47$419,900
5 bd · 3 ba · 1,936 sqft
8630 Elm Rd, Chestertown, MD
Lawrence M. Lessin · Save 6, Incorporated
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
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
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 Reduced43$825,000
5 bd · 4 ba · 2,639 sqft
7680 Country Club Ln, Chestertown, MD
John J Burke · Gunther-McClary Real Estate
Price Reduced22$299,500
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 Reduced3$79,000
2 bd · 1 ba · 1,296 sqft
234 N College Ave, Chestertown, MD
Anastasia Marie Zivkovic Palmer · Cummings & Co Realtors
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 Reduced60$1,495,000
9 bd · 7 ba · 4,776 sqft
8796 Maryland Pkwy, Chestertown, MD
Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company
Price Reduced29$275,000
3 bd · 1 ba · 1,248 sqft
956 Washington Ave, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
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
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$799,900
3 bd · 4 ba · 2,472 sqft
106 Queen St S, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
Price Reduced73$1,500,000
7 bd · 5 ba · 5,400 sqft
117 Water St N #1a, 1B, 2a, & 2B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
23$350,000
1 bd · 1 ba · 850 sqft
117 Water St N #2B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
20$200,000
1 bd · 1 ba · 700 sqft
117 Water St N #1B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
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October 2026 · This period is still settling