Chestertown, MD - single-family homes for sale

45 of 45 results displayed

New
$329,900Active
4 beds 2 baths1,325 sq. ft.
304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006482Listed by: REDFIN CORPORATION
Coming Soon
$215,000Coming Soon
3 beds 1 baths
100 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006544Listed by: REAL BROKER, LLC
$325,000Pending
3 beds 1 baths1,427 sq. ft.
202 Valley Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006538Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
Coming Soon
$425,000Coming Soon
3 beds 2 baths
8629 Airy Hill Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006526Listed by: KELLER WILLIAMS REALTY
Coming Soon
$525,000Coming Soon
3 beds 2 baths
110 S Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006520Listed by: CROSS STREET REALTORS LLC
Coming Soon
$395,000Coming Soon
5 beds 4 baths
107 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006510Listed by: CENTURY 21 NEW MILLENNIUM
New
$350,000Active
4 beds 3 baths1,972 sq. ft.
214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
$828,000Active
3 beds 5 baths3,047 sq. ft.
407 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006496Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$179,000Active
2 beds 2 baths1,082 sq. ft.
144 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006494Listed by: DOUG ASHLEY REALTORS, LLC
$419,900Active
3 beds 3 baths1,944 sq. ft.
103 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006416Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$550,000Active
5 beds 4 baths3,816 sq. ft.
103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$115,000Active
3 beds 1 baths910 sq. ft.
108 Pine St, CHESTERTOWN, MD 21620
MLS# MDKE2006322Listed by: REAL BROKER, LLC
$435,000Pending
3 beds 2 baths1,588 sq. ft.
201 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006316Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$225,000Active
3 beds 1 baths1,200 sq. ft.
139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP
$340,000Active
3 beds 2 baths2,055 sq. ft.
202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$419,900Active
3 beds 3 baths1,216 sq. ft.
109 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006040Listed by: TAYLOR PROPERTIES
$865,000Active
3 beds 4 baths2,472 sq. ft.
106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$394,900Active
5 beds 4 baths2,535 sq. ft.
104 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006212Listed by: REAL BROKER, LLC
$269,900Pending
3 beds 1 baths1,356 sq. ft.
112 Elm St, CHESTERTOWN, MD 21620
MLS# MDKE2006192Listed by: COLDWELL BANKER WATERMAN REALTY
$299,900Pending
3 beds 2 baths1,152 sq. ft.
301 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006170Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$1,150,000Active
5 beds 3 baths2,956 sq. ft.
231 Richard Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005900Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$375,000Active
2 beds 1 baths787 sq. ft.
117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active
1 beds 1 baths850 sq. ft.
117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,600,000Active
7 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
$685,000Active
3 beds 3 baths3,000 sq. ft.
117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$200,000Active
1 beds 1 baths700 sq. ft.
117 Water St N #1b, CHESTERTOWN, MD 21620
MLS# MDKE2006164Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$750,000Active
-- beds -- baths2,045 sq. ft.
201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$157,400Pending
2 beds 1 baths910 sq. ft.
132 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006110Listed by: ANR REALTY, LLC
Open Sat, 10am to 12pm
$510,000Active
5 beds 4 baths3,932 sq. ft.
218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER REALTY
$450,000Active
4 beds 3 baths2,880 sq. ft.
110 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005964Listed by: RE/MAX ADVANTAGE REALTY
$753,500Active
3 beds 3 baths1,964 sq. ft.
#36 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005958Listed by: GUNTHER-MCCLARY REAL ESTATE
$765,900Active
3 beds 3 baths1,964 sq. ft.
#37 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005960Listed by: GUNTHER-MCCLARY REAL ESTATE
$786,900Active
3 beds 3 baths1,964 sq. ft.
#35 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005956Listed by: GUNTHER-MCCLARY REAL ESTATE
$839,500Active
3 beds 3 baths1,964 sq. ft.
102 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005950Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,099,900Active
4 beds 4 baths2,784 sq. ft.
#25 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005954Listed by: GUNTHER-MCCLARY REAL ESTATE
$499,000Active
4 beds 3 baths3,504 sq. ft.
311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Active
2 beds 2 baths920 sq. ft.
611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$1,459,000Active
3 beds 3 baths2,231 sq. ft.
Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2005768Listed by: GUNTHER-MCCLARY REAL ESTATE
$849,900Active
3 beds 3 baths1,980 sq. ft.
104 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005894Listed by: GUNTHER-MCCLARY REAL ESTATE
$434,999Active
4 beds 2 baths1,656 sq. ft.
222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
Open Sun, 11am to 1pm
$2,200,000Active
5 beds 5 baths4,305 sq. ft.
7989 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005590Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$509,000Active
5 beds 4 baths4,067 sq. ft.
116 Harlan Loop, CHESTERTOWN, MD 21620
MLS# MDKE2005610Listed by: SAMSON PROPERTIES
$130,000Active
2 beds 1 baths1,296 sq. ft.
234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005434Listed by: CUMMINGS & CO REALTORS
$1,800,000Active
4 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
$1,295,500Active
5 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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Company

About ERA real estate blog Franchise ERA global Contact us

Buy and sell

Buy information Sell information ERA Distinctive Properties All homes for sale All real estate agents All real estate offices

Resources

Find an agent Join ERA Offices

Terms of use Accessibility statement DMCA notice Fraud alert Privacy notice Fair housing Do not sell or share my personal information Submit agent or broker complaint

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.

© 2023 - 2026 ERA Franchise Systems LLC. All rights reserved. ERA Franchise Systems LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. ERA, ERA Real Estate powered, and their respective logos are registered service marks of ERA Franchise Systems LLC. Each office is independently owned and operated.