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Chestertown, MD - condos for sale
46 of 46 results displayed
- New
$10,000Active0.55 AcresBuck Neck Landing Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005586Listed by: ROSENDALE REALTY - New
$40,000Active0.34 AcresTonopah Rd., CHESTERTOWN, MD 21620
MLS# MDKE2005564Listed by: THE HOGANS AGENCY - Coming Soon
$795,000Coming Soon4 beds 4 baths200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC - Coming Soon
$450,000Coming Soon3 beds 2 baths224 Valley Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005546Listed by: CROSS STREET REALTORS LLC - Open Sat, 11am to 1pm
$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
$12,675Pending0.22 AcresElm Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005532Listed by: CROSS STREET REALTORS LLC
$175,000Active4 beds 2 baths1,156 sq. ft.141 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2005504Listed by: CROSS STREET REALTORS LLC
$280,000Active3 beds 2 baths1,280 sq. ft.112 Metcalf Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005498Listed by: ENGEL & VOLKERS ANNAPOLIS
$325,000Active1 beds 2 baths936 sq. ft.108 S Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2005496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$325,000Active3 beds 2 baths2,212 sq. ft.205 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2005492Listed by: DAVIS REAL ESTATE, INC.
$15,000Active0.34 AcresCogar Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005472Listed by: COMPASS
$209,900Active3 beds 3 baths1,199 sq. ft.304 Hilltop Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005440Listed by: DOUG ASHLEY REALTORS, LLC
$184,900Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$815,000Active2 beds 2 baths1,401 sq. ft.209 Rivershore Rd, CHESTERTOWN, MD 21620
MLS# MDQA2013938Listed by: DOUGLAS REALTY LLC
$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
$103,000Active0.48 AcresEast St, CHESTERTOWN, MD 21620
MLS# MDQA2013494Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$575,000Active3.01 Acres136 Truslow Farm Ln, CHESTERTOWN, MD 21620
MLS# MDQA2013478Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$3,000,000Pending87.34 AcresCromwell Clark Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005156Listed by: THE LAND GROUP
$1,550,000Active5 beds 4 baths4,167 sq. ft.7961 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005090Listed by: COMPASS
$549,000Active3 beds 2 baths1,961 sq. ft.101 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005088Listed by: CROSS STREET REALTORS LLC
$1,459,000Active3 beds 3 baths2,315 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2004992Listed by: GUNTHER-MCCLARY REAL ESTATE
$220,000Active3 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
$49,900Active1.51 AcresCloquet Rd, CHESTERTOWN, MD 21620
MLS# MDKE2004960Listed by: BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
$998,000Active3 beds 4 baths226 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2004940Listed by: GUNTHER-MCCLARY REAL ESTATE
$5,000Active0.34 AcresTowhee Rd, CHESTERTOWN, MD 21620
MLS# MDKE2004882Listed by: ASHLAND AUCTION GROUP LLC
$349,900Pending3 beds 3 baths1,856 sq. ft.110 Flying Cloud Court, CHESTERTOWN, MD 21620
MLS# MDKE2004850Listed by: BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
$299,000Active3 beds 2 baths1,224 sq. ft.866 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005480Listed by: BRENTON REALTY GROUP
$299,000Active3 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
$759,000Active3 beds 4 baths212 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2004782Listed by: GUNTHER-MCCLARY REAL ESTATE
$495,000Active3 beds 2 baths2,767 sq. ft.116 Pine Chip Rd, CHESTERTOWN, MD 21620
MLS# MDQA2010882Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$569,000Active2 beds 3 baths2,100 sq. ft.103 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2004972Listed by: GUNTHER-MCCLARY REAL ESTATE
$725,000Active3 beds 3 baths117 N Water St #1a, CHESTERTOWN, MD 21620
MLS# MDKE2004206Listed by: GUNTHER-MCCLARY REAL ESTATE
$395,000Active7 beds 4 baths3,664 sq. ft.349 High St, CHESTERTOWN, MD 21620
MLS# MDKE2004076Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$212,000Active1.95 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
$395,000Active6 beds -- baths3,664 sq. ft.349 & 351 High St, CHESTERTOWN, MD 21620
MLS# MDKE2003720Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$55,000Active0.7 AcresMap 36 Parcel 80 Watertower Rd, CHESTERTOWN, MD 21620
MLS# MDKE2003624Listed by: DOUG ASHLEY REALTORS, LLC
$8,000Active0.42 AcresLot 24 & 25 Buck Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2004828Listed by: DOUG ASHLEY REALTORS, LLC
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.