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4, Chestertown, MD - homes for sale
44 of 44 results displayed
- Open Sat, 11am to 1pmNew
$449,900Active3 beds 3 baths1,216 sq. ft.109 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005818Listed by: CROSS STREET REALTORS LLC - Coming SoonOpen Sat, 11am to 1pm
$363,000Coming Soon3 beds 2 baths303 E Campus Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005756Listed by: DOUG ASHLEY REALTORS, LLC - New
$619,000Active4 beds 4 baths2,008 sq. ft.206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2005840Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$695,000Active4 beds 4 baths3,735 sq. ft.8951 Orchard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005836Listed by: ROCK HALL PROPERTIES REAL ESTATE 
$269,000Active3 beds 2 baths960 sq. ft.318 Lincoln, CHESTERTOWN, MD 21620
MLS# MDKE2005842Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY- Coming SoonOpen Sat, 11am to 1pm
$419,000Coming Soon3 beds 3 baths411 Greenwood Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005824Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - Open Sat, 9:30am to 12pm
$878,000Active3 beds 4 baths2,310 sq. ft.228 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2005812Listed by: GUNTHER-MCCLARY REAL ESTATE 
$499,999Active3 beds 2 baths1,961 sq. ft.101 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005810Listed by: REMAX VISION
$290,000Active3 beds 1 baths1,200 sq. ft.107 Malone Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005764Listed by: DOUGLAS REALTY LLC
$639,900Active4 beds 2 baths2,869 sq. ft.206 Valley, CHESTERTOWN, MD 21620
MLS# MDKE2005762Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$1,250,000Pending5 beds 5 baths4,409 sq. ft.119 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005728Listed by: CROSS STREET REALTORS LLC
$165,000Active3 beds 2 baths1,136 sq. ft.423 Calvert St, CHESTERTOWN, MD 21620
MLS# MDKE2005718Listed by: REDFIN CORP
$795,000Pending4 beds 3 baths2,736 sq. ft.201 Radcliffe Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005732Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$389,900Active3 beds -- baths1,728 sq. ft.517 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005736Listed by: L. C. PARKER REAL ESTATE
$230,000Pending3 beds 2 baths1,140 sq. ft.126 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005734Listed by: TAYLOR PROPERTIES
$374,900Active5 beds 4 baths2,615 sq. ft.112 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005706Listed by: EXP REALTY, LLC
$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
$250,000Active3 beds 2 baths1,140 sq. ft.100 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005634Listed by: BAYSIDE REALTY
$499,900Active4 beds 2 baths2,220 sq. ft.515 N Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2005592Listed by: CROSS STREET REALTORS LLC
$519,000Active5 beds 4 baths4,067 sq. ft.116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$745,000Pending3 beds 4 baths2,492 sq. ft.110 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2005558Listed by: GUNTHER-MCCLARY REAL ESTATE
$595,000Pending4 beds 4 baths5,576 sq. ft.103 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005594Listed by: DOUGLAS REALTY LLC
$695,000Active4 beds 4 baths2,917 sq. ft.200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC
$410,000Pending3 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
$249,950Active3 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
$62,400Active2 beds 1 baths910 sq. ft.132 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2005444Listed by: ANR REALTY, LLC
$164,000Pending2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$625,000Pending3 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
$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- Open Sun, 11am to 1pm
$1,395,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005002Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$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
Local realty services provided by:Better Homes and Gardens Real Estate GSA Realty
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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 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.