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21620, MD - single-family homes for sale
76 of 76 results displayed
- New
$335,000Active3 beds 2 baths1,412 sq. ft.10720 Foreston Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006800Listed by: COMPASS - Coming Soon
$325,000Coming Soon3 beds 3 baths109 Cedar St, CHESTERTOWN, MD 21620
MLS# MDKE2006792Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY 
$385,000Pending3 beds 2 baths1,934 sq. ft.521 N Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2006784Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY- Open Sun, 11am to 1pmNew
$885,000Active5 beds 4 baths2,639 sq. ft.7680 Country Club Ln, CHESTERTOWN, MD 21620
MLS# MDKE2006758Listed by: GUNTHER-MCCLARY REAL ESTATE - Open Sat, 11am to 1pmNew
$344,000Active3 beds 2 baths1,216 sq. ft.9126 Fairlee Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006764Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC 
$325,000Active3 beds 1 baths1,000 sq. ft.896 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006750Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY- Coming Soon
$735,000Coming Soon4 beds 3 baths210 N Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006744Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$279,900Active3 beds 2 baths1,296 sq. ft.22481 Goose Hollow Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006682Listed by: KELLER WILLIAMS LEGACY
$299,900Active3 beds 1 baths1,248 sq. ft.517 Round Top Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017680Listed by: KELLER WILLIAMS FLAGSHIP
$629,900Pending3 beds 2 baths2,430 sq. ft.201 River Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017684Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$228,000Pending3 beds 2 baths2,260 sq. ft.221 Dutchess Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017670Listed by: DOUG ASHLEY REALTORS, LLC
$615,000Pending4 beds 3 baths4,536 sq. ft.103 Maple Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006676Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$365,000Pending3 beds 2 baths1,248 sq. ft.23264 Clarissa Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006096Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$515,000Active2 beds 3 baths1,476 sq. ft.101 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2006674Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$100,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006670Listed by: CUMMINGS & CO REALTORS
$468,000Active3 beds 2 baths3,262 sq. ft.25750 Collins Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006546Listed by: DOUG ASHLEY REALTORS, LLC
$79,900Active3 beds 2 baths2,210 sq. ft.110 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006626Listed by: ANR REALTY, LLC
$200,000Active4 beds 1 baths2,920 sq. ft.21172 Wyoming Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006642Listed by: BLUE STAR REAL ESTATE, LLC
$325,000Pending3 beds 2 baths1,404 sq. ft.10572 Watonga Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006644Listed by: SERHANT
$429,900Active4 beds 3 baths2,160 sq. ft.10781 Fermoy Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006640Listed by: REAL BROKER, LLC - CHESTER
$380,000Active4 beds 2 baths1,277 sq. ft.213 Byford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006026Listed by: DOUG ASHLEY REALTORS, LLC
$1,200,000Pending4 beds 3 baths2,292 sq. ft.202 Royston Shores Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017462Listed by: CROSS STREET REALTORS LLC
$265,000Active3 beds 1 baths1,967 sq. ft.1904 Pondtown Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017480Listed by: KELLER WILLIAMS FLAGSHIP
$399,900Active2 beds 3 baths1,518 sq. ft.522 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006614Listed by: BENSON & MANGOLD, LLC
$1,650,000Active9 beds 7 baths4,776 sq. ft.8796 Maryland Pkwy, CHESTERTOWN, MD 21620
MLS# MDKE2006596Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$3,000,000Pending3 beds 4 baths3,142 sq. ft.25440 Learman Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006468Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$329,900Active3 beds 3 baths1,896 sq. ft.102 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006586Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,450,000Active4 beds 5 baths4,257 sq. ft.22470 Fairgale Farm Ln, CHESTERTOWN, MD 21620
MLS# MDKE2006502Listed by: GUNTHER-MCCLARY REAL ESTATE
$309,900Pending4 beds 2 baths1,325 sq. ft.304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006482Listed by: REDFIN CORPORATION
$215,000Pending3 beds 1 baths1,373 sq. ft.100 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006544Listed by: REAL BROKER, LLC - CHESTER
$525,000Pending3 beds 2 baths1,785 sq. ft.110 S Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006520Listed by: CROSS STREET REALTORS LLC
$375,000Active5 beds 4 baths2,534 sq. ft.107 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006510Listed by: CENTURY 21 NEW MILLENNIUM
$340,000Active4 beds 3 baths1,972 sq. ft.214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
$798,000Pending3 beds 5 baths3,047 sq. ft.407 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$535,000Pending3 beds 3 baths1,624 sq. ft.9816 Fairlee Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006488Listed by: LONG & FOSTER REAL ESTATE, INC.
$425,000Pending3 beds 3 baths1,784 sq. ft.215 Fairview Dr, CHESTERTOWN, MD 21620
MLS# MDQA2017090Listed by: LONG & FOSTER REAL ESTATE, INC.
$320,000Active3 beds 2 baths1,232 sq. ft.8706 Elm Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006390Listed by: DOUG ASHLEY REALTORS, LLC
$299,000Active3 beds 1 baths1,120 sq. ft.208 Central Dr, CHESTERTOWN, MD 21620
MLS# MDQA2016836Listed by: REDFIN CORP
$430,000Pending2 beds 3 baths1,857 sq. ft.24295 Langford Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006320Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$365,000Active3 beds 2 baths1,120 sq. ft.240 Merganser Dr, CHESTERTOWN, MD 21620
MLS# MDQA2016900Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$244,500Pending2 beds 1 baths912 sq. ft.21217 Texas Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006364Listed by: RE/MAX LEADING EDGE
$550,000Active5 beds 4 baths3,816 sq. ft.103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$440,000Pending3 beds 3 baths2,060 sq. ft.704 Truslow Rd, CHESTERTOWN, MD 21620
MLS# MDQA2016632Listed by: RE/MAX EXECUTIVE
$198,000Pending3 beds 1 baths1,200 sq. ft.139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP
$519,900Active3 beds 3 baths2,268 sq. ft.101 Coleman Dr, CHESTERTOWN, MD 21620
MLS# MDQA2016624Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$340,000Pending3 beds 2 baths2,055 sq. ft.202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$865,000Active3 beds 4 baths2,472 sq. ft.106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$1,395,000Active4 beds 4 baths3,383 sq. ft.8276 Broad Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006216Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$375,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active1 beds 1 baths850 sq. ft.117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,600,000Active7 beds 5 baths5,400 sq. ft.117 Water St N #1a, 1b, 2a, & 2b, CHESTERTOWN, MD 21620
MLS# MDKE2006158Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$685,000Active3 beds 3 baths3,000 sq. ft.117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$200,000Active1 beds 1 baths700 sq. ft.117 Water St N #1b, CHESTERTOWN, MD 21620
MLS# MDKE2006164Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$750,000Active-- beds 2 baths2,045 sq. ft.201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$565,000Active3 beds 3 baths2,927 sq. ft.204 Double Creek Rd, CHESTERTOWN, MD 21620
MLS# MDQA2015996Listed by: DOUG ASHLEY REALTORS, LLC
$384,000Active5 beds 3 baths3,371 sq. ft.6746 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006014Listed by: DOUG ASHLEY REALTORS, LLC
$319,900Pending3 beds 1 baths1,008 sq. ft.24775 Langford Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005992Listed by: RE/MAX ADVANTAGE REALTY
$499,999Active5 beds 4 baths3,932 sq. ft.218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$753,500Active3 beds 3 baths1,964 sq. ft.#36 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005958Listed by: GUNTHER-MCCLARY REAL ESTATE
$765,900Active3 beds 3 baths1,964 sq. ft.#37 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005960Listed by: GUNTHER-MCCLARY REAL ESTATE
$786,900Active3 beds 3 baths1,964 sq. ft.#35 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005956Listed by: GUNTHER-MCCLARY REAL ESTATE
$839,500Active3 beds 3 baths1,964 sq. ft.102 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005950Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,099,900Active4 beds 4 baths2,784 sq. ft.#25 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005954Listed by: GUNTHER-MCCLARY REAL ESTATE
$475,000Pending4 beds 3 baths3,504 sq. ft.311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Pending2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$1,459,000Active3 beds 3 baths2,231 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2005768Listed by: GUNTHER-MCCLARY REAL ESTATE
$849,900Active3 beds 3 baths1,980 sq. ft.104 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005894Listed by: GUNTHER-MCCLARY REAL ESTATE- Open Sat, 12 to 2pm
$419,999Active4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC. 
$499,900Active4 beds 3 baths2,524 sq. ft.8620 Park Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005850Listed by: DOUG ASHLEY REALTORS, LLC
$670,000Pending4 beds 3 baths3,248 sq. ft.7844 Chester Ct, CHESTERTOWN, MD 21620
MLS# MDKE2005796Listed by: DOUG ASHLEY REALTORS, LLC
$320,000Active3 beds 2 baths1,096 sq. ft.222 Dutchess Rd, CHESTERTOWN, MD 21620
MLS# MDQA2014830Listed by: GUNTHER-MCCLARY REAL ESTATE
$385,000Active4 beds 3 baths2,630 sq. ft.23043 Bay Shore Spur, CHESTERTOWN, MD 21620
MLS# MDKE2005584Listed by: ROCK HALL PROPERTIES REAL ESTATE- Open Sat, 11am to 1pm
$2,200,000Active5 beds 5 baths4,305 sq. ft.7989 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005590Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$1,800,000Active4 beds 4 baths3,540 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2004992Listed by: GUNTHER-MCCLARY REAL ESTATE- Open Sat, 10am to 12pm
$1,245,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$425,000Pending3 beds 2 baths3,280 sq. ft.24543 Chestertown Rd, CHESTERTOWN, MD 21620
MLS# MDKE2004580Listed by: RE/MAX EXECUTIVE
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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.