Chestertown, MD - single-family homes for sale

40 of 40 results displayed

$325,000Active
4 beds 2 baths2,198 sq. ft.
200 Manor Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006808Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$325,000Pending
3 beds 3 baths1,397 sq. ft.
109 Cedar St, CHESTERTOWN, MD 21620
MLS# MDKE2006792Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$325,000Active
3 beds 1 baths1,000 sq. ft.
896 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006750Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$735,000Pending
4 beds 3 baths2,730 sq. ft.
210 N Queen St, CHESTERTOWN, MD 21620
MLS# MDKE2006744Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$629,900Pending
3 beds 2 baths2,430 sq. ft.
201 River Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017684Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$615,000Pending
4 beds 3 baths4,536 sq. ft.
103 Maple Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006676Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$515,000Pending
2 beds 3 baths1,476 sq. ft.
101 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2006674Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$85,000Active
2 beds 1 baths1,296 sq. ft.
234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006670Listed by: CUMMINGS & CO REALTORS
$69,900Active
3 beds 2 baths2,210 sq. ft.
110 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006626Listed by: ANR REALTY, LLC
$380,000Active
4 beds 2 baths1,277 sq. ft.
213 Byford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006026Listed by: DOUG ASHLEY REALTORS, LLC
$350,000Active
2 beds 3 baths1,518 sq. ft.
522 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006614Listed by: BENSON & MANGOLD, LLC
$329,900Pending
3 beds 3 baths1,896 sq. ft.
102 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006586Listed by: LONG & FOSTER REAL ESTATE, INC.
$309,900Pending
4 beds 2 baths1,325 sq. ft.
304 Hadaway Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006482Listed by: REDFIN CORPORATION
$375,000Pending
5 beds 4 baths2,534 sq. ft.
107 Flying Cloud Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006510Listed by: CENTURY 21 NEW MILLENNIUM
$340,000Pending
4 beds 3 baths1,972 sq. ft.
214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
$798,000Pending
3 beds 5 baths3,047 sq. ft.
407 High St, CHESTERTOWN, MD 21620
MLS# MDKE2006496Listed 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
$198,000Pending
3 beds 1 baths1,200 sq. ft.
139 Prospect St, CHESTERTOWN, MD 21620
MLS# MDKE2006250Listed by: REDFIN CORP
$340,000Pending
3 beds 2 baths2,055 sq. ft.
202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$829,000Active
3 beds 4 baths2,472 sq. ft.
106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$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 2 baths2,045 sq. ft.
201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$499,999Active
5 beds 4 baths3,932 sq. ft.
218 Camelot Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005982Listed by: COLDWELL BANKER 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
$475,000Pending
4 beds 3 baths3,504 sq. ft.
311 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2005930Listed by: DOUG ASHLEY REALTORS, LLC
$275,000Pending
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
$419,999Active
4 beds 2 baths1,656 sq. ft.
222 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2005876Listed by: LONG & FOSTER REAL ESTATE, INC.
$2,200,000Pending
5 beds 5 baths4,305 sq. ft.
7989 Quaker Neck Rd, CHESTERTOWN, MD 21620
MLS# MDKE2005590Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$1,800,000Active
4 beds 4 baths3,540 sq. ft.
Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2004992Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,245,500Active
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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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation 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.

©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.