Cheap Homes For Sale in Chestertown, MD

66 homes

Use arrow keys to navigate
$85,000
2 Beds
1 Bath
1,296 sqft
234 N College Ave,
Chestertown, MD 21620
Cummings & Co. Realtors
Use arrow keys to navigate
$145,000
3 Beds
1.5 Baths
1,192 sqft
409 Calvert St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
Use arrow keys to navigate
3D VIEW
$179,900
2 Beds
1 Bath
1,232 sqft
21324 Persimmon Dr,
Chestertown, MD 21620
Benson & Mangold, LLC
Use arrow keys to navigate
3D VIEW
$200,000
1 Bed
1 Bath
700 sqft
117 N Water St #1B,
Chestertown, MD 21620
TTR Sotheby's International Realty
Use arrow keys to navigate
COMING SOON 9/1
0.55 ACRES
$225,000
4 Beds
1.5 Baths
1,800 sqft
533 Round Top Rd,
Chestertown, MD 21620
EXP Realty, LLC
Use arrow keys to navigate
$239,900
3 Beds
1.5 Baths
1,280 sqft
104 Conley Dr,
Chestertown, MD 21620
Cummings & Co. Realtors
Use arrow keys to navigate
NEW CONSTRUCTION
$259,900
3 Beds
1.5 Baths
1,280 sqft
115 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
COMING SOON 9/4
$263,000
3 Beds
2 Baths
1,140 sqft
115 Chester Arms Dr,
Chestertown, MD 21620
Samson Properties
NEW CONSTRUCTION
$264,900
3 Beds
1.5 Baths
121 Metcalf Rd,
Chestertown, MD 21620
Real Broker, 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
0.34 ACRES
$279,000
3 Beds
2 Baths
1,404 sqft
10540 Tonopah Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$295,000
1 Bed
1 Bath
117 N Water St #3B,
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
3D VIEW
0.34 ACRES
$304,000
3 Beds
2 Baths
1,232 sqft
7464 Shortall St,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
OPEN SAT, 10-12PM
COMING SOON 9/2
0.34 ACRES
$315,000
3 Beds
2 Baths
1,288 sqft
109 Parma Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
0.33 ACRES
$320,000
3 Beds
2 Baths
1,232 sqft
8706 Elm Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.67 ACRES
$320,000
3 Beds
1.5 Baths
1,096 sqft
222 Dutchess Rd,
Chestertown, MD 21620
Gunther-McClary Real Estate
1.66 ACRES
$324,000
3 Beds
1.5 Baths
1,216 sqft
9126 Fairlee Rd,
Chestertown, MD 21620
Chesapeake Real Estate Associates, 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
0.34 ACRES
$325,000
3 Beds
1 Bath
1,000 sqft
896 Washington Ave,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
COMING SOON 9/2
0.34 ACRES
$345,000
3 Beds
1.5 Baths
1,398 sqft
217 Edmore Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.68 ACRES
$349,000
5 Beds
2.5 Baths
3,371 sqft
6746 Quaker Neck 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
3D VIEW
$350,000
1 Bed
1 Bath
850 sqft
117 N Water St #2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
$369,000
2 Beds
1.5 Baths
1,036 sqft
101 S College Ave,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
3D VIEW
0.34 ACRES
$372,000
4 Beds
2 Baths
1,277 sqft
213 Byford Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.74 ACRES
$375,000
4 Beds
2 Baths
1,476 sqft
1010 Twin Ct,
Chestertown, MD 21620
Kevin Dey Realty
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
0.38 ACRES
$424,900
5 Beds
2.5 Baths
1,936 sqft
8630 Elm Rd,
Chestertown, MD 21620
Save 6, Incorporated
FOR SALE BY OWNER
3 ACRES
$425,000
4 Beds
2.5 Baths
3,165 sqft
106 Harlan Loop,
Chestertown, MD 21620
0.39 ACRES
$429,900
4 Beds
2.5 Baths
2,160 sqft
10781 Fermoy Rd,
Chestertown, MD 21620
Real Broker, LLC
FOR SALE BY OWNER
0.47 ACRES
$435,000
3 Beds
2 Baths
2,081 sqft
233 Duke Of Kent St,
Chestertown, MD 21620
AUCTION
0.28 ACRES
Est. $444,900
4 Beds
3 Baths
1,944 sqft
110 Trafford Dr,
Chestertown, MD 21620
3D VIEW
0.8 ACRES
$478,000
2 Beds
2 Baths
1,904 sqft
7982 Radcliffe Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
0.25 ACRES
$480,000
3 Beds
2.5 Baths
3,176 sqft
129 Trafford Dr,
Chestertown, MD 21620
Elevated Real Estate Solutions
3D VIEW
1.37 ACRES
$489,900
4 Beds
2.5 Baths
2,524 sqft
8620 Park Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
$499,999
2 Beds
2.5 Baths
2,100 sqft
103 Landing Ln,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
Save Search in Chestertown, MD
Chestertown
1+ Beds
House
Condo
Townhome
Multi-Family
Mobile/Manufactured
Get emails when new homes match this search

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 Chestertown, MD

66 homes

Save Search in Chestertown, MD

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Maryland

Chestertown Neighborhoods

Chestertown Property Types

Real Estate Guides