Cheap Homes For Sale in 21620

66 homes

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$85,000
2 Beds
1 Bath
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
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3D VIEW
$200,000
1 Bed
1 Bath
700 sqft
117 N Water St #1B,
Chestertown, MD 21620
TTR Sotheby's International Realty
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3D VIEW
0.34 ACRES
$229,000
3 Beds
1 Bath
936 sqft
7415 Wilkins Ln,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
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$239,900
3 Beds
1.5 Baths
1,280 sqft
104 Conley Dr,
Chestertown, MD 21620
Cummings & Co. Realtors
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$259,000
3 Beds
2 Baths
1,140 sqft
115 Chester Arms Dr,
Chestertown, MD 21620
Samson Properties
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OPEN TUE, 6-7PM
NEW CONSTRUCTION
$259,900
3 Beds
1.5 Baths
1,280 sqft
115 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
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NEW - 2 DAYS AGO
NEW CONSTRUCTION
$259,900
3 Beds
2.5 Baths
1,280 sqft
103 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
NEW CONSTRUCTION
$264,900
3 Beds
1.5 Baths
121 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
0.34 ACRES
$269,000
3 Beds
2 Baths
1,404 sqft
10540 Tonopah Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$275,000
3 Beds
2.5 Baths
1,900 sqft
104 Acorn Dr,
Chestertown, MD 21620
Cross Street Realtors LLC
3D VIEW
0.69 ACRES
$275,000
3 Beds
1 Bath
1,248 sqft
956 Washington Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OPEN SAT, 10-12PM
3D VIEW
0.5 ACRES
$285,000
3 Beds
1 Bath
960 sqft
104 Lincoln Dr,
Chestertown, MD 21620
RE/MAX Executive
OPEN SAT, 2-3:30PM
0.33 ACRES
$289,000
3 Beds
2 Baths
1,056 sqft
8732 Elm Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
3D VIEW
0.34 ACRES
$299,900
3 Beds
1 Bath
1,056 sqft
124 Wilton Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
NEW - 1 DAY AGO
FORECLOSURE
BANK OWNED
$312,500
3 Beds
2 Baths
1,080 sqft
8820 Cumberland St,
Chestertown, MD 21620
RE/MAX Advantage Realty
1.66 ACRES
$314,000
3 Beds
1.5 Baths
1,216 sqft
9126 Fairlee Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.33 ACRES
$315,000
3 Beds
2 Baths
1,232 sqft
8706 Elm Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
1.22 ACRES
$315,000
3 Beds
1 Bath
1,008 sqft
24775 Langford Rd,
Chestertown, MD 21620
RE/MAX Chesapeake
0.67 ACRES
$320,000
3 Beds
1.5 Baths
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
3D VIEW
0.47 ACRES
$325,000
4 Beds
2 Baths
2,198 sqft
200 Manor Ave,
Chestertown, MD 21620
TTR Sotheby's International Realty
0.34 ACRES
$325,000
3 Beds
1 Bath
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
3D VIEW
0.5 ACRES
$329,900
2 Beds
2 Baths
1,440 sqft
22974 Bay Shore Rd,
Chestertown, MD 21620
Benson & Mangold, LLC
0.34 ACRES
$335,000
3 Beds
1.5 Baths
1,398 sqft
217 Edmore Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.68 ACRES
$339,000
5 Beds
2.5 Baths
3,371 sqft
6746 Quaker Neck Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.74 ACRES
$349,900
4 Beds
2 Baths
1,476 sqft
1010 Twin Ct,
Chestertown, MD 21620
Kevin Dey Realty
NEW CONSTRUCTION
0.34 ACRES
$349,900
3 Beds
2.5 Baths
1,650 sqft
23208 Buck Neck Rd,
Chestertown, MD 21620
Real Broker, LLC
3D VIEW
$350,000
1 Bed
1 Bath
850 sqft
117 N Water St #2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
$359,000
2 Beds
1.5 Baths
1,036 sqft
101 S College Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
FORECLOSURE
NOTICE OF DEFAULT
4 Beds
2.5 Baths
2,504 sqft
123 Trafford Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
3D VIEW
$375,000
2 Beds
1 Bath
787 sqft
117 N Water St #2A,
Chestertown, MD 21620
TTR Sotheby's International Realty
1.65 ACRES
$385,000
4 Beds
3 Baths
2,630 sqft
23043 Bay Shore Spur,
Chestertown, MD 21620
Rock Hall Properties Real Estate
FOR SALE BY OWNER
3 ACRES
$395,000
4 Beds
2.5 Baths
3,165 sqft
106 Harlan Loop,
Chestertown, MD 21620
3D VIEW
0.8 ACRES
$399,000
2 Beds
2 Baths
1,904 sqft
7982 Radcliffe Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
FOR SALE BY OWNER
0.47 ACRES
$420,000
3 Beds
2 Baths
2,081 sqft
233 Duke Of Kent St,
Chestertown, MD 21620
OPEN SAT, 12-3PM
0.38 ACRES
$424,900
5 Beds
2.5 Baths
1,936 sqft
8630 Elm Rd,
Chestertown, MD 21620
Save 6, Incorporated
0.39 ACRES
$429,500
4 Beds
2.5 Baths
2,160 sqft
10781 Fermoy Rd,
Chestertown, MD 21620
Real Broker, LLC
AUCTION
0.28 ACRES
Est. $443,400
4 Beds
3 Baths
1,944 sqft
110 Trafford Dr,
Chestertown, MD 21620
0.25 ACRES
$480,000
3 Beds
2.5 Baths
3,176 sqft
129 Trafford Dr,
Chestertown, MD 21620
Elevated Real Estate Solutions
OPEN SAT, 11-1PM
$489,000
2 Beds
2 Baths
1,098 sqft
105 N Water St #3,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
COMING SOON 10/16
0.53 ACRES
$495,000
3 Beds
2.5 Baths
1,656 sqft
10 Cedar Chase Ct,
Chestertown, MD 21620
Cross Street Realtors LLC
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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Cheap Homes For Sale in 21620

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