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4, Chestertown, MD - homes for sale
30 of 30 results displayed
- Coming Soon
$249,500Coming Soon3 beds 2 baths112 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006090Listed by: ROSENDALE REALTY 
$650,000Pending4 beds 2 baths2,064 sq. ft.109 Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006064Listed by: CROSS STREET REALTORS LLC
$585,000Active4 beds 4 baths2,008 sq. ft.206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006058Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$165,000Active4 beds 2 baths1,156 sq. ft.141 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006036Listed by: TAYLOR PROPERTIES
$495,000Pending4 beds 3 baths3,984 sq. ft.201 Greenwood Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006030Listed by: DOUG ASHLEY REALTORS, LLC
$333,900Pending3 beds 3 baths2,577 sq. ft.303 Cedar St, CHESTERTOWN, MD 21620
MLS# MDKE2005970Listed by: SELECT LAND & HOMES, LLC
$525,000Active5 beds 4 baths3,932 sq. ft.218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$264,900Active3 beds 2 baths1,280 sq. ft.109 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005968Listed by: REAL BROKER, LLC
$475,000Active4 beds 3 baths2,880 sq. ft.110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$598,000Active5 beds 4 baths3,504 sq. ft.311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$364,900Pending4 beds 3 baths1,936 sq. ft.108 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005928Listed by: CROSS STREET REALTORS LLC
$299,000Active2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$345,000Pending3 beds 2 baths2,296 sq. ft.204 Rolling Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005896Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$455,000Active4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$350,000Active4 beds 2 baths1,325 sq. ft.304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005848Listed by: CUMMINGS & CO. REALTORS
$878,000Active3 beds 4 baths2,310 sq. ft.228 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2005812Listed by: GUNTHER-MCCLARY REAL ESTATE
$135,000Pending3 beds 2 baths1,136 sq. ft.423 Calvert St, CHESTERTOWN, MD 21620
MLS# MDKE2005718Listed by: REDFIN CORP
$259,900Active3 beds 2 baths1,280 sq. ft.103 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005688Listed by: REAL BROKER, LLC
$500,000Active4 beds 4 baths3,799 sq. ft.100 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005636Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$509,000Active5 beds 4 baths4,067 sq. ft.116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$695,000Pending4 beds 4 baths2,917 sq. ft.200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC
$595,000Active3 beds 3 baths3,935 sq. ft.251 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005536Listed by: DOUG ASHLEY REALTORS, LLC
$164,000Pending2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$3,000,000Active87.34 AcresCromwell Clark Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005156Listed by: THE LAND GROUP
$1,395,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$225,000Pending0.96 AcresHaacke Drive Lot 3, CHESTERTOWN, MD 21620
MLS# MDKE2004648Listed by: SELECT LAND & HOMES, LLC
$250,000Pending0.93 AcresScheeler Road Lot 2, CHESTERTOWN, MD 21620
MLS# MDKE2004650Listed by: SELECT LAND & HOMES, LLC
$395,000Pending7 beds 4 baths3,664 sq. ft.349 High St, CHESTERTOWN, MD 21620
MLS# MDKE2004076Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$185,000Pending1.95 AcresLot 9 Prestwick Dr, CHESTERTOWN, MD 21620
MLS# MDKE2003918Listed by: GUNTHER-MCCLARY REAL ESTATE
$395,000Pending6 beds -- baths3,664 sq. ft.349 & 351 High St, CHESTERTOWN, MD 21620
MLS# MDKE2003720Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
Local realty services provided by:Better Homes and Gardens Real Estate Reserve
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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.