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Chestertown, MD - single-family homes for sale
42 of 42 results displayed
- Coming Soon
$524,900Coming Soon3 beds 3 baths2,076 sq. ft.1003 Twin Ct, CHESTERTOWN, MD 21620
MLS# MDKE2006974Listed by: CROSS STREET REALTORS LLC - Coming Soon
$263,000Coming Soon3 beds 2 baths1,140 sq. ft.115 Chester Arms Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006958Listed by: SAMSON PROPERTIES - Coming Soon
$369,000Coming Soon2 beds 2 baths1,036 sq. ft.101 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006918Listed by: DOUG ASHLEY REALTORS, LLC - New
$478,000Active2 beds 2 baths1,904 sq. ft.7982 Radcliffe Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006950Listed by: DOUG ASHLEY REALTORS, LLC - New
$375,000Active4 beds 3 baths2,504 sq. ft.123 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006970Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC - New
$750,000Active3 beds 3 baths2,176 sq. ft.216 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006896Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY 
$440,000Active2 beds 2 baths1,058 sq. ft.104 Church Aly, CHESTERTOWN, MD 21620
MLS# MDKE2006900Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$480,000Active3 beds 3 baths3,176 sq. ft.129 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006878Listed by: ELEVATED REAL ESTATE SOLUTIONS
$135,000Pending4 beds 2 baths1,152 sq. ft.207 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006894Listed by: MONUMENT SOTHEBY'S INTERNATIONAL REALTY
$205,000Pending3 beds 1 baths1,341 sq. ft.202 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006888Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$325,000Active4 beds 2 baths2,198 sq. ft.200 Manor Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006808Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$325,000Active3 beds 1 baths1,000 sq. ft.896 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006750Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$735,000Pending4 beds 3 baths2,730 sq. ft.210 N Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006744Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$629,900Pending3 beds 2 baths2,430 sq. ft.201 River Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017684Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$615,000Pending4 beds 3 baths4,536 sq. ft.103 Maple Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006676Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$515,000Pending2 beds 3 baths1,476 sq. ft.101 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2006674Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$85,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006670Listed by: CUMMINGS & CO REALTORS
$54,900Pending3 beds 2 baths2,210 sq. ft.110 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006626Listed by: ANR REALTY, LLC
$380,000Active4 beds 2 baths1,277 sq. ft.213 Byford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006026Listed by: DOUG ASHLEY REALTORS, LLC
$289,900Pending2 beds 3 baths1,518 sq. ft.522 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006614Listed by: BENSON & MANGOLD, LLC
$340,000Pending4 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
$550,000Active5 beds 4 baths3,816 sq. ft.103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$340,000Pending3 beds 2 baths2,055 sq. ft.202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$829,000Active3 beds 4 baths2,472 sq. ft.106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$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
$1,500,000Active7 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
$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
$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
$419,999Pending4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$1,245,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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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.