Homes For Sale in Chestertown, MD Under $400k

77 homes

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$200,000
4 Beds
1 Bath
1,816 sqft
223 Mount Vernon Ave,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
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3D VIEW
0.5 ACRES
$329,900
2 Beds
2 Baths
1,440 sqft
22974 Bay Shore Rd,
Chestertown, MD 21620
Benson & Mangold, LLC
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1.22 ACRES
$315,000
3 Beds
1 Bath
1,008 sqft
24775 Langford Rd,
Chestertown, MD 21620
RE/MAX Chesapeake
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0.33 ACRES
$289,000
3 Beds
2 Baths
1,056 sqft
8732 Elm Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
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NEW CONSTRUCTION
BUILDABLE PLAN
Studio
Homes Available Soon Plan in Radcliffe Meadows Single Family Homes,
Chestertown, MD 21620
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NEW CONSTRUCTION
BUILDABLE PLAN
Studio
Homes Available Soon Plan in Radcliffe Meadows Villas,
Chestertown, MD 21620
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3D VIEW
0.5 ACRES
$295,000
3 Beds
1 Bath
960 sqft
104 Lincoln Dr,
Chestertown, MD 21620
RE/MAX Executive
0.45 ACRES
$275,000
3 Beds
1 Bath
975 sqft
7482 Poplar Ave,
Chestertown, MD 21620
Taylor Properties
0.55 ACRES
$50,000
Towhee Rd,
Chestertown, MD 21620
The Parker Group
0.34 ACRES
$335,000
3 Beds
1.5 Baths
1,398 sqft
217 Edmore Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$263,000
3 Beds
2 Baths
1,140 sqft
115 Chester Arms Dr,
Chestertown, MD 21620
Samson Properties
5.17 ACRES
$89,000
27942 Old Morgnec Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
3D VIEW
0.34 ACRES
$229,000
3 Beds
1 Bath
936 sqft
7415 Wilkins Ln,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$359,000
2 Beds
1.5 Baths
1,036 sqft
101 S College Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
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 CONSTRUCTION
0.34 ACRES
$349,900
3 Beds
2.5 Baths
1,650 sqft
23208 Buck Neck Rd,
Chestertown, MD 21620
Real Broker, LLC
FORECLOSURE
NOTICE OF DEFAULT
4 Beds
2.5 Baths
2,504 sqft
123 Trafford Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.34 ACRES
$269,000
3 Beds
2 Baths
1,404 sqft
10540 Tonopah Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$196,000
Cannon St,
Chestertown, MD 21620
Taylor Properties
$85,000
620 Cannon St,
Chestertown, MD 21620
Taylor Properties
0.74 ACRES
$369,900
4 Beds
2 Baths
1,476 sqft
1010 Twin Ct,
Chestertown, MD 21620
Kevin Dey Realty
$300,000
201 N Lynchburg St #&-7,
Chestertown, MD 21620
RE/MAX Associates-Hockessin
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
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
0.5 ACRES
$60,000
233 Merganser Dr,
Chestertown, MD 21620
Long & Foster Real Estate, Inc.
NEW CONSTRUCTION
$264,900
3 Beds
1.5 Baths
121 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
0.61 ACRES
$45,000
305 Roosevelt Dr,
Chestertown, MD 21620
Taylor Properties
OPEN SUN, 11-12:30PM
1.66 ACRES
$314,000
3 Beds
1.5 Baths
1,216 sqft
9126 Fairlee Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
0.34 ACRES
$325,000
3 Beds
1 Bath
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
$239,900
3 Beds
1.5 Baths
1,280 sqft
104 Conley Dr,
Chestertown, MD 21620
Cummings & Co. Realtors
$85,000
2 Beds
1 Bath
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
$275,000
3 Beds
2.5 Baths
1,900 sqft
104 Acorn Dr,
Chestertown, MD 21620
Cross Street Realtors LLC
2.2 ACRES
$75,000
Fairlee Rd,
Chestertown, MD 21620
RE/MAX Chesapeake
3D VIEW
0.34 ACRES
$372,000
4 Beds
2 Baths
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
4.03 ACRES
$69,900
8886 Georgetown Rd,
Chestertown, MD 21620
Samson Properties
1 ACRE
$15,000
23741 L Rd,
Chestertown, MD 21620
Benson & Mangold, 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
0.7 ACRES
$55,000
Map 36 Watertower Rd #80,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
1.95 ACRES
$49,000
Sandy Bottom Rd,
Chestertown, MD 21620
Village Real Estate Company LLC
1.8 ACRES
$135,000
109 2nd St,
Chestertown, MD 21620
Cross Street Realtors LLC
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Chestertown
$0 - $400k
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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

Homes For Sale in Chestertown, MD Under $400k

77 homes

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