4, Chestertown, MD Homes for Sale | The Joy of Home with CENTURY21

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Coming Soon
$249,500Coming Soon
3 beds 2 baths
112 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006090Listed by: ROSENDALE REALTY
New
$650,000Active
4 beds 2 baths2,064 sq. ft.
109 Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006064Listed by: CROSS STREET REALTORS LLC
$585,000Active
4 beds 4 baths2,008 sq. ft.
206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006058Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$165,000Active
4 beds 2 baths1,156 sq. ft.
141 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006036Listed by: TAYLOR PROPERTIES
$495,000Pending
4 beds 3 baths3,984 sq. ft.
201 Greenwood Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006030Listed by: DOUG ASHLEY REALTORS, LLC
$333,900Pending
3 beds 3 baths2,577 sq. ft.
303 Cedar St, CHESTERTOWN, MD 21620
MLS# MDKE2005970Listed by: SELECT LAND & HOMES, LLC
$525,000Active
5 beds 4 baths3,932 sq. ft.
218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$264,900Active
3 beds 2 baths1,280 sq. ft.
109 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005968Listed by: REAL BROKER, LLC
$475,000Active
4 beds 3 baths2,880 sq. ft.
110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$598,000Active
5 beds 4 baths3,504 sq. ft.
311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$364,900Pending
4 beds 3 baths1,936 sq. ft.
108 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005928Listed by: CROSS STREET REALTORS LLC
$299,000Active
2 beds 2 baths920 sq. ft.
611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$345,000Pending
3 beds 2 baths2,296 sq. ft.
204 Rolling Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005896Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$455,000Active
4 beds 2 baths1,656 sq. ft.
222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$350,000Active
4 beds 2 baths1,325 sq. ft.
304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005848Listed by: CUMMINGS & CO. REALTORS
$878,000Active
3 beds 4 baths2,310 sq. ft.
228 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2005812Listed by: GUNTHER-MCCLARY REAL ESTATE
$135,000Pending
3 beds 2 baths1,136 sq. ft.
423 Calvert St, CHESTERTOWN, MD 21620
MLS# MDKE2005718Listed by: REDFIN CORP
$259,900Active
3 beds 2 baths1,280 sq. ft.
103 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005688Listed by: REAL BROKER, LLC
$500,000Active
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
$695,000Pending
4 beds 4 baths2,917 sq. ft.
200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC
$595,000Active
3 beds 3 baths3,935 sq. ft.
251 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005536Listed by: DOUG ASHLEY REALTORS, LLC
$164,000Pending
2 beds 1 baths1,296 sq. ft.
234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$3,000,000Active
87.34 Acres
Cromwell Clark Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005156Listed by: THE LAND GROUP
$1,395,500Active
5 beds 5 baths3,243 sq. ft.
105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$225,000Pending
0.96 Acres
Haacke Drive Lot 3, CHESTERTOWN, MD 21620
MLS# MDKE2004648Listed by: SELECT LAND & HOMES, LLC
$250,000Pending
0.93 Acres
Scheeler Road Lot 2, CHESTERTOWN, MD 21620
MLS# MDKE2004650Listed by: SELECT LAND & HOMES, LLC
$395,000Pending
7 beds 4 baths3,664 sq. ft.
349 High St, CHESTERTOWN, MD 21620
MLS# MDKE2004076Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$185,000Pending
1.95 Acres
Lot 9 Prestwick Dr, CHESTERTOWN, MD 21620
MLS# MDKE2003918Listed by: GUNTHER-MCCLARY REAL ESTATE
$395,000Pending
6 beds -- baths3,664 sq. ft.
349 & 351 High St, CHESTERTOWN, MD 21620
MLS# MDKE2003720Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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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

©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.