21620 Single Family Homes For Sale

44 homes

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$395,000
5 Beds
3.5 Baths
2,534 sqft
107 Flying Cloud Dr,
Chestertown, MD 21620
CENTURY 21 New Millennium
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NEW - 2 DAYS AGO
$205,000
3 Beds
1 Bath
1,314 sqft
21363 Lynn Ln,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
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0.34 ACRES
$384,000
3 Beds
2 Baths
1,512 sqft
23416 Cloquet Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
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0.41 ACRES
$329,900
4 Beds
2 Baths
1,325 sqft
304 Hadaway Dr,
Chestertown, MD 21620
Redfin Corporation
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COMING SOON 5/28
$215,000
3 Beds
1 Bath
1,373 sqft
100 Prospect St,
Chestertown, MD 21620
Real Broker, LLC
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COMING SOON 5/20
2.16 ACRES
$425,000
3 Beds
2 Baths
1,440 sqft
8629 Airy Hill Rd,
Chestertown, MD 21620
Keller Williams Realty
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$350,000
4 Beds
2.5 Baths
1,972 sqft
214 Silver Heel Rd,
Chestertown, MD 21620
Cross Street Realtors LLC
COMING SOON 5/22
$525,000
3 Beds
1.5 Baths
1,785 sqft
110 S Queen St,
Chestertown, MD 21620
Cross Street Realtors LLC
$179,000
2 Beds
1.5 Baths
1,082 sqft
144 Prospect St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
COMING SOON 5/22
0.73 ACRES
$499,000
3 Beds
2 Baths
1,817 sqft
1014 Twin Ct,
Chestertown, MD 21620
Cross Street Realtors LLC
6.29 ACRES
$535,000
3 Beds
3 Baths
1,624 sqft
9816 Fairlee Rd,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
$828,000
3 Beds
4.5 Baths
3,047 sqft
407 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
AUCTION
Est. $281,800
3 Beds
2 Baths
1,080 sqft
8820 Cumberland St,
Chestertown, MD 21620
$419,900
3 Beds
2.5 Baths
1,944 sqft
103 Trafford Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
NEW CONSTRUCTION
1.01 ACRES
$899,500
4 Beds
2.5 Baths
2,877 sqft
205 River Rd,
Chestertown, MD 21620
Clark & Co Realty, LLC
0.33 ACRES
$320,000
3 Beds
2 Baths
1,232 sqft
8706 Elm Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.55 ACRES
$299,000
3 Beds
1 Bath
1,120 sqft
208 Central Dr,
Chestertown, MD 21620
Redfin Corp
COMING SOON 6/4
2 ACRES
$445,000
2 Beds
2.5 Baths
1,857 sqft
24295 Langford Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
COMING SOON 5/30
0.51 ACRES
$425,000
3 Beds
2 Baths
1,120 sqft
240 Merganser Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.37 ACRES
$244,500
2 Beds
1 Bath
912 sqft
21217 Texas Ave,
Chestertown, MD 21620
RE/MAX Leading Edge
$550,000
5 Beds
3.5 Baths
3,816 sqft
103 Sutton Way,
Chestertown, MD 21620
TTR Sotheby's International Realty
OPEN SAT, 11-2PM
$865,000
3 Beds
3.5 Baths
2,472 sqft
106 S Queen St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
$115,000
3 Beds
1 Bath
910 sqft
108 Pine St,
Chestertown, MD 21620
Real Broker, LLC
$394,900
5 Beds
3.5 Baths
2,535 sqft
104 Flying Cloud Dr,
Chestertown, MD 21620
Real Broker, LLC
1.1 ACRES
$524,900
3 Beds
2.5 Baths
2,268 sqft
101 Coleman Dr,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$225,000
3 Beds
1 Bath
1,200 sqft
139 Prospect St,
Chestertown, MD 21620
Redfin Corp
0.34 ACRES
$340,000
3 Beds
1.5 Baths
2,055 sqft
202 Waldo Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$419,900
3 Beds
2.5 Baths
1,216 sqft
109 S College Ave,
Chestertown, MD 21620
Taylor Properties
19.81 ACRES
$1,495,000
4 Beds
3.5 Baths
3,383 sqft
8276 Broad Neck Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
0.76 ACRES
$344,900
3 Beds
2 Baths
1,392 sqft
109 Wilton Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.79 ACRES
$1,150,000
5 Beds
3 Baths
2,956 sqft
231 Richard Dr,
Chestertown, MD 21620
TTR Sotheby's International Realty
0.87 ACRES
$598,000
3 Beds
2.5 Baths
2,927 sqft
204 Double Creek Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.68 ACRES
$384,000
5 Beds
2.5 Baths
3,371 sqft
6746 Quaker Neck Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.28 ACRES
$450,000
4 Beds
2.5 Baths
2,880 sqft
110 Trafford Dr,
Chestertown, MD 21620
RE/MAX Advantage Realty
$510,000
5 Beds
3.5 Baths
3,932 sqft
218 Camelot Dr,
Chestertown, MD 21620
Coldwell Banker Realty
0.28 ACRES
$499,000
4 Beds
3 Baths
3,504 sqft
311 Devon Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$275,000
2 Beds
1.5 Baths
920 sqft
611 Cannon St,
Chestertown, MD 21620
Select Land & Homes, LLC
$1,295,500
5 Beds
4.5 Baths
3,243 sqft
105 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$434,999
4 Beds
2 Baths
1,656 sqft
222 Mount Vernon Ave,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
1.37 ACRES
$499,900
4 Beds
2.5 Baths
2,524 sqft
8620 Park Dr,
Chestertown, MD 21620
Doug Ashley 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

21620 Single Family Homes For Sale

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