View 218 Camelot Drive Chestertown, MD MLS# MDKE2005982
$499,999
5

Beds

3.1

Baths

3,932

Sq.Ft.

218 Camelot Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$450,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
$475,000
4

Beds

3.0

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Georgetown Road Chestertown, MD MLS# MDKE2005844
$90,000
Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
$635,000
Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
$275,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$429,999
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Clarissa Road Chestertown, MD MLS# MDKE2005786
$10,000
Studio

Beds

0.0

Baths

Clarissa Road

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 103 Landing Lane Chestertown, MD MLS# MDKE2005670
$499,999
2

Beds

2.1

Baths

2,100

Sq.Ft.

103 Landing Lane

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 23043 Bay Shore Spur Chestertown, MD MLS# MDKE2005584
$385,000
4

Beds

3.0

Baths

2,630

Sq.Ft.

23043 Bay Shore Spur

Chestertown, MD

Bright
Courtesy of ROCK HALL PROPERTIES REAL ESTATE
View Buck Neck Landing Road Chestertown, MD MLS# MDKE2005586
$10,000
Studio

Beds

0.0

Baths

Buck Neck Landing Road

Chestertown, MD

Bright
Courtesy of ROSENDALE REALTY
View Tonopah Rd. Chestertown, MD MLS# MDKE2005564
$40,000
Studio

Beds

0.0

Baths

Tonopah Rd.

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View Johnsontown Road Chestertown, MD MLS# MDKE2005550
$25,000
Studio

Beds

0.0

Baths

Johnsontown Road

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View Kinglet Road Chestertown, MD MLS# MDKE2005260
$9,000
Studio

Beds

0.0

Baths

Kinglet Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Buck Neck Road Chestertown, MD MLS# MDKE2005262
$9,000
Studio

Beds

0.0

Baths

Buck Neck Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Georgetown Rd Chestertown, MD MLS# MDKE2005218
$60,000
Studio

Beds

0.0

Baths

Georgetown Rd

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Caulks Field Road Chestertown, MD MLS# MDKE2005120
$150,000
Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

Bright
Courtesy of RE/MAX ALLEGIANCE
View Georgetown Road SE Chestertown, MD MLS# MDKE2005076
$150,000
Studio

Beds

0.0

Baths

Georgetown Road SE

Chestertown, MD

Bright
Courtesy of RE/MAX ALLEGIANCE
View Old Morgnec Road Chestertown, MD MLS# MDKE2004974
$59,000
Studio

Beds

0.0

Baths

Old Morgnec Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

About Chestertown

Home of George Washington College, Chestertown is the center of amenities and the hub of life in Kent County.  Located on the banks of the Chester River, Chestertown began as a prosperous shipbuilding, trade and government center during the colonial movement and still maintains the state’s oldest records.  The popular autumn Candlelight Walking Tour offers a glimpse into many of the spectacular homes built by wealthy merchants of the 18th and 19th centuries.  Quaint red-brick sidewalks and broad, shaded streets form an idyllic backdrop for specialty shops, galleries and eateries.  On cool summer evenings, residents can relax to the strains of concerts held around the antique fountain in the town square.  Lovely homes, a stimulating college-town atmosphere and community pride make Chestertown the ideal place to call home. 

Listings in Chestertown, MD

126

Estimated median home price

$357,500
Chestertown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

Homes for Sale by Price in Chestertown, MD

PriceCount
$0 - 100K32
$100K - 200K10
$200K - 300K14
$300K - 400K17
$400K - 500K13
$500K - 600K5
$600K - 700K4
$700K - 800K8
$800K - 900K6
$900K - 1M0
$1M - Max17

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family53
Townhouse7
Condo16
Commercial10
Rental14
Lots and Land40
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/19/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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