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4, Chestertown, MD - homes for sale
38 of 38 results displayed
- New
$259,900Active3 beds 2 baths1,280 sq. ft.103 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005688Listed by: REAL BROKER, LLC 
$515,000Active4 beds 4 baths3,799 sq. ft.100 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005636Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$255,000Active3 beds 2 baths1,140 sq. ft.100 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005634Listed by: BAYSIDE REALTY
$509,900Active4 beds 2 baths2,220 sq. ft.515 N Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2005592Listed by: CROSS STREET REALTORS LLC
$529,000Active5 beds 4 baths4,067 sq. ft.116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$675,000Pending4 beds 3 baths3,820 sq. ft.8978 Orchard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005500Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$745,000Pending3 beds 4 baths2,492 sq. ft.110 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2005558Listed by: GUNTHER-MCCLARY REAL ESTATE
$595,000Active4 beds 4 baths5,576 sq. ft.103 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005594Listed by: DOUGLAS REALTY LLC
$745,000Active4 beds 4 baths2,917 sq. ft.200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC
$450,000Pending3 beds 2 baths1,886 sq. ft.224 Valley Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005546Listed by: CROSS STREET REALTORS LLC
$440,000Active3 beds 3 baths1,842 sq. ft.907 N Meadowview Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005540Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$595,000Active3 beds 3 baths3,935 sq. ft.251 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005536Listed by: DOUG ASHLEY REALTORS, LLC
$167,000Active4 beds 2 baths1,156 sq. ft.141 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2005504Listed by: CROSS STREET REALTORS LLC
$265,000Active3 beds 2 baths1,280 sq. ft.112 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005498Listed by: ENGEL & VOLKERS ANNAPOLIS
$315,000Active1 beds 2 baths936 sq. ft.108 S Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2005496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$325,000Pending3 beds 2 baths2,212 sq. ft.205 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2005492Listed by: DAVIS REAL ESTATE, INC.
$209,900Pending3 beds 3 baths1,199 sq. ft.304 Hilltop Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005440Listed by: DOUG ASHLEY REALTORS, LLC
$164,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$625,000Active3 beds 3 baths1,600 sq. ft.26933 Mallard Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005422Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$470,000Active3 beds 2 baths1,588 sq. ft.201 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005380Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$648,750Active4 beds 4 baths2,008 sq. ft.206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2005362Listed by: DOUG ASHLEY REALTORS, LLC
$480,000Pending3 beds 2 baths1,820 sq. ft.206 Barroll Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005094Listed by: CROSS STREET REALTORS LLC
$240,000Active2 beds 1 baths1,290 sq. ft.624 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005274Listed by: TESLA REALTY GROUP, LLC
$3,000,000Pending87.34 AcresCromwell Clark Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005156Listed by: THE LAND GROUP
$220,000Pending3 beds 3 baths1,200 sq. ft.300 Hilltop Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005004Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$1,395,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005002Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$998,000Active3 beds 4 baths226 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2004940Listed by: GUNTHER-MCCLARY REAL ESTATE
$334,900Active3 beds 3 baths1,856 sq. ft.110 Flying Cloud Court, CHESTERTOWN, MD 21620
MLS# MDKE2004850Listed by: BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
$330,000Active3 beds 2 baths1,224 sq. ft.866 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005480Listed by: BRENTON REALTY GROUP
$330,000Active3 beds -- baths1,224 sq. ft.866 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005460Listed by: BRENTON REALTY GROUP
$225,000Active0.96 AcresHaacke Drive Lot 3, CHESTERTOWN, MD 21620
MLS# MDKE2004648Listed by: SELECT LAND & HOMES, LLC
$250,000Active0.93 AcresScheeler Road Lot 2, CHESTERTOWN, MD 21620
MLS# MDKE2004650Listed by: SELECT LAND & HOMES, LLC
$1,150,000Active1.56 Acres206 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2003620Listed by: BENSON & MANGOLD, LLC
$725,000Active3 beds 3 baths117 N Water St #1a, CHESTERTOWN, MD 21620
MLS# MDKE2004206Listed by: GUNTHER-MCCLARY REAL ESTATE
$395,000Pending7 beds 4 baths3,664 sq. ft.349 High St, CHESTERTOWN, MD 21620
MLS# MDKE2004076Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$185,000Active1.95 AcresLot 9 Prestwick Dr, CHESTERTOWN, MD 21620
MLS# MDKE2003918Listed by: GUNTHER-MCCLARY REAL ESTATE
$399,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2003742Listed 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
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Protect your home and budget with an American Home Shield© home warranty. Learn more© 2025 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.