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Chestertown, MD - single-family homes for sale
28 of 28 results displayed
- Coming Soon
$525,000Coming Soon4 beds 4 baths206 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006124Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC - New
$199,885Active2 beds 1 baths910 sq. ft.132 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006110Listed by: ANR REALTY, LLC - New
$344,900Active4 beds 2 baths1,325 sq. ft.304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006116Listed by: CUMMINGS & CO. REALTORS 
$549,000Active4 beds 4 baths2,008 sq. ft.206 S Water St, CHESTERTOWN, MD 21620
MLS# MDKE2006058Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$165,000Pending4 beds 2 baths1,156 sq. ft.141 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006036Listed by: TAYLOR PROPERTIES
$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
$475,000Active4 beds 3 baths2,880 sq. ft.110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE 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
$580,000Active5 beds 4 baths3,504 sq. ft.311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$364,900Pending4 beds 3 baths1,936 sq. ft.108 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005928Listed by: CROSS STREET REALTORS LLC
$299,000Active2 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
$345,000Pending3 beds 2 baths2,296 sq. ft.204 Rolling Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005896Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$449,999Active4 beds 2 baths1,656 sq. ft.222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$500,000Active4 beds 4 baths3,799 sq. ft.100 Adela Way, CHESTERTOWN, MD 21620
MLS# MDKE2005636Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
$2,500,000Active5 beds 5 baths4,305 sq. ft.7989 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005590Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$509,000Active5 beds 4 baths4,067 sq. ft.116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$695,000Pending4 beds 4 baths2,917 sq. ft.200 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005538Listed by: CROSS STREET REALTORS LLC
$595,000Active3 beds 3 baths3,935 sq. ft.251 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005536Listed by: DOUG ASHLEY REALTORS, LLC
$164,000Pending2 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
Local realty services provided by:Better Homes and Gardens Real Estate Valley Partners
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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.