4, Chestertown, MD - single-family homes for sale

32 of 32 results displayed

Coming Soon

$395,000Coming Soon
5 beds 4 baths
107 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006510Listed by: CENTURY 21 NEW MILLENNIUM
Coming Soon
$350,000Coming Soon
4 beds 3 baths
214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
Open Sat, 10am to 1pmNew
$828,000Active
3 beds 5 baths3,047 sq. ft.
407 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
Coming Soon
$179,000Coming Soon
2 beds 2 baths
144 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006494Listed by: DOUG ASHLEY REALTORS, LLC
Open Sat, 10am to 12pm
$419,900Active
3 beds 3 baths1,944 sq. ft.
103 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006416Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$550,000Active
5 beds 4 baths3,816 sq. ft.
103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$115,000Active
3 beds 1 baths910 sq. ft.
108 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006322Listed by: REAL BROKER, LLC
$435,000Pending
3 beds 2 baths1,588 sq. ft.
201 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006316Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$225,000Active
3 beds 1 baths1,200 sq. ft.
139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP
$340,000Pending
3 beds 2 baths2,055 sq. ft.
202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$419,900Active
3 beds 3 baths1,216 sq. ft.
109 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006040Listed by: TAYLOR PROPERTIES
$865,000Active
3 beds 4 baths2,472 sq. ft.
106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$399,900Active
5 beds 4 baths2,535 sq. ft.
104 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006212Listed by: REAL BROKER, LLC
$269,900Pending
3 beds 1 baths1,356 sq. ft.
112 Elm St, CHESTERTOWN, MD 21620
MLS# MDKE2006192Listed by: COLDWELL BANKER WATERMAN REALTY
$299,900Pending
3 beds 2 baths1,152 sq. ft.
301 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006170Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$1,150,000Active
5 beds 3 baths2,956 sq. ft.
231 Richard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005900Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$375,000Active
2 beds 1 baths787 sq. ft.
117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active
1 beds 1 baths850 sq. ft.
117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,600,000Active
7 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
$685,000Active
3 beds 3 baths3,000 sq. ft.
117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$200,000Active
1 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
$157,400Pending
2 beds 1 baths910 sq. ft.
132 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006110Listed by: ANR REALTY, LLC
$510,000Active
5 beds 4 baths3,932 sq. ft.
218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$450,000Active
4 beds 3 baths2,880 sq. ft.
110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$499,000Active
4 beds 3 baths3,504 sq. ft.
311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Active
2 beds 2 baths920 sq. ft.
611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$434,999Active
4 beds 2 baths1,656 sq. ft.
222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$498,500Pending
4 beds 4 baths3,799 sq. ft.
100 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005636Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$509,000Active
5 beds 4 baths4,067 sq. ft.
116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$130,000Active
2 beds 1 baths1,296 sq. ft.
234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$1,295,500Active
5 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:CENTURY 21 Harbor Realty

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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.