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Chestertown, Chestertown, MD - single-family homes for sale
35 of 35 results displayed
- New
$325,000Active3 beds 2 baths1,404 sq. ft.217 Philosophers Ter, CHESTERTOWN, MD 21620
MLS# MDKE2006332Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$115,000Active3 beds 1 baths910 sq. ft.108 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006322Listed by: REAL BROKER, LLC - New
$435,000Active3 beds 2 baths1,588 sq. ft.201 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006316Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$339,900Pending3 beds 3 baths1,724 sq. ft.103 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006154Listed by: AMERICAN PREMIER REALTY, LLC- Open Sat, 11am to 1pmNew
$225,000Active3 beds 1 baths1,200 sq. ft.139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP - New
$389,000Active3 beds 2 baths2,055 sq. ft.202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC 
$419,900Active3 beds 3 baths1,216 sq. ft.109 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006040Listed by: TAYLOR PROPERTIES- Open Fri, 5 to 7pm
$865,000Active3 beds 4 baths2,472 sq. ft.106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC 
$399,900Active5 beds 4 baths2,535 sq. ft.104 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006212Listed by: REAL BROKER, LLC
$495,000Pending4 beds 3 baths2,220 sq. ft.515 N Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2006204Listed by: CROSS STREET REALTORS LLC
$269,900Active3 beds 1 baths1,356 sq. ft.112 Elm St, CHESTERTOWN, MD 21620
MLS# MDKE2006192Listed by: COLDWELL BANKER WATERMAN REALTY
$309,900Active3 beds 2 baths1,152 sq. ft.301 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006170Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$1,279,000Active5 beds 3 baths2,956 sq. ft.231 Richard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005900Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$375,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active7 beds 6 baths850 sq. ft.117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,600,000Active7 beds 6 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
$795,000Active-- beds 2 baths2,045 sq. ft.201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$499,000Pending4 beds 4 baths2,186 sq. ft.206 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006124Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$159,900Active2 beds 1 baths910 sq. ft.132 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006110Listed by: ANR REALTY, LLC
$549,000Pending4 beds 4 baths2,008 sq. ft.206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006058Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$495,000Pending4 beds 3 baths3,984 sq. ft.201 Greenwood Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006030Listed by: DOUG ASHLEY REALTORS, LLC
$525,000Active5 beds 4 baths3,932 sq. ft.218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$465,000Active4 beds 3 baths2,880 sq. ft.110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$839,500Active3 beds 3 baths1,964 sq. ft.102 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005950Listed by: GUNTHER-MCCLARY REAL ESTATE
$525,000Active5 beds 4 baths3,504 sq. ft.311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Active2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$849,900Active3 beds 3 baths1,980 sq. ft.104 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005894Listed by: GUNTHER-MCCLARY REAL ESTATE
$444,999Active4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$498,500Pending4 beds 4 baths3,799 sq. ft.100 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005636Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$509,000Active5 beds 4 baths4,067 sq. ft.116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$130,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$1,800,000Active4 beds 4 baths3,540 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2004992Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,395,500Active5 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.