34$325,000
4 bd · 2 ba · 2,198 sqft
200 Manor Ave, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Homes for Sale in Chestertown, MD
Hide MapHomes for Sale in Chestertown, MD
24 of 61 Listings
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
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$85,000
2 bd · 1 ba · 1,296 sqft
234 N College Ave, Chestertown, MD
Anastasia Marie Zivkovic Palmer · Cummings & Co Realtors
Price Reduced54$429,500
4 bd · 3 ba · 2,160 sqft
10781 Fermoy 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 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
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
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
20$200,000
1 bd · 1 ba · 700 sqft
117 Water St N #1B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
24$375,000
2 bd · 1 ba · 787 sqft
117 Water St N #2a, 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
46$685,000
3 bd · 3 ba · 3,000 sqft
117 Water St N #1a, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Price Reduced50$339,000
5 bd · 3 ba · 3,371 sqft
6746 Quaker Neck Rd, Chestertown, MD
Michele A Palmer · Doug Ashley Realtors, LLC
Price Reduced13$750,000
0 bd · 2 ba · 2,045 sqft
201 N Lynchburg St, Chestertown, MD
John W. Ford · RE/MAX Associates-Hockessin
26$786,900
3 bd · 3 ba · 1,964 sqft
#35 Landing Ln, Chestertown, MD
Julia Hilfiker · Gunther-McClary Real Estate
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