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4, Chestertown, MD - single-family homes for sale
35 of 35 results displayed
- Coming Soon
$615,000Coming Soon4 beds 3 baths103 Maple Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006676Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - Open Sat, 11am to 1pmNew
$515,000Active2 beds 3 baths1,476 sq. ft.101 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2006674Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$100,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006670Listed by: CUMMINGS & CO REALTORS - New
$119,895Active3 beds 2 baths2,210 sq. ft.110 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006626Listed by: ANR REALTY, LLC 
$380,000Active4 beds 2 baths1,277 sq. ft.213 Byford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006026Listed by: DOUG ASHLEY REALTORS, LLC
$425,000Active2 beds 3 baths1,518 sq. ft.522 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006614Listed by: BENSON & MANGOLD, LLC
$339,900Active3 beds 3 baths1,896 sq. ft.102 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006586Listed by: LONG & FOSTER REAL ESTATE, INC.
$314,900Active4 beds 2 baths1,325 sq. ft.304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006482Listed by: REDFIN CORPORATION
$215,000Pending3 beds 1 baths1,373 sq. ft.100 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006544Listed by: REAL BROKER, LLC - CHESTER
$525,000Pending3 beds 2 baths1,785 sq. ft.110 S Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006520Listed by: CROSS STREET REALTORS LLC
$385,000Active5 beds 4 baths2,534 sq. ft.107 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006510Listed by: CENTURY 21 NEW MILLENNIUM
$340,000Active4 beds 3 baths1,972 sq. ft.214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
$798,000Active3 beds 5 baths3,047 sq. ft.407 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$159,000Pending2 beds 2 baths1,082 sq. ft.144 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006494Listed by: DOUG ASHLEY REALTORS, LLC- Open Sat, 11am to 1pm
$399,900Active3 beds 3 baths1,944 sq. ft.103 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006416Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$550,000Active5 beds 4 baths3,816 sq. ft.103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$115,000Pending3 beds 1 baths910 sq. ft.108 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006322Listed by: REAL BROKER, LLC - CHESTER
$225,000Active3 beds 1 baths1,200 sq. ft.139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP
$340,000Pending3 beds 2 baths2,055 sq. ft.202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$419,900Pending3 beds 3 baths1,216 sq. ft.109 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006040Listed by: TAYLOR PROPERTIES
$865,000Active3 beds 4 baths2,472 sq. ft.106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$394,900Active5 beds 4 baths2,535 sq. ft.104 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006212Listed by: REAL BROKER, LLC - CHESTER
$1,150,000Pending5 beds 3 baths2,956 sq. ft.231 Richard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005900Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$375,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active1 beds 1 baths850 sq. ft.117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,600,000Active7 beds 5 baths5,400 sq. ft.117 Water St N #1a, 1b, 2a, & 2b, CHESTERTOWN, MD 21620
MLS# MDKE2006158Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$685,000Active3 beds 3 baths3,000 sq. ft.117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$200,000Active1 beds 1 baths700 sq. ft.117 Water St N #1b, CHESTERTOWN, MD 21620
MLS# MDKE2006164Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$750,000Active-- beds 2 baths2,045 sq. ft.201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$499,999Active5 beds 4 baths3,932 sq. ft.218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$450,000Active4 beds 3 baths2,880 sq. ft.110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$475,000Active4 beds 3 baths3,504 sq. ft.311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Active2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$429,999Active4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,295,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
Local realty services provided by:Better Homes and Gardens Real Estate Premier
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© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.