View Melitota Road Chestertown, MD MLS# MDKE2004834
$29,000
Studio

Beds

0.0

Baths

Melitota Road

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View Caulks Field Road Chestertown, MD MLS# MDKE2002846
$28,000
Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 23710 L Road Chestertown, MD MLS# MDKE2002838
$24,000
Studio

Beds

0.0

Baths

23710 L Road

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View Elm Road Chestertown, MD MLS# MDKE2003590
$20,000
Studio

Beds

0.0

Baths

Elm Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Sheldrake Drive Chestertown, MD MLS# MDKE2001692
$15,000
Studio

Beds

0.0

Baths

Sheldrake Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 22681 Wood Yard Lane Chestertown, MD MLS# MDKE2004720
$15,000
Studio

Beds

0.0

Baths

22681 Wood Yard Lane

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Parcel Buck Neck Ldg Road Chestertown, MD MLS# MDKE2003874
$10,000
Studio

Beds

0.0

Baths

Parcel Buck Neck Ldg Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Fish Hatchery Road Chestertown, MD MLS# MDKE2004754
$10,000
Studio

Beds

0.0

Baths

Fish Hatchery Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Beltram Rd Chestertown, MD MLS# MDKE2004756
$10,000
Studio

Beds

0.0

Baths

Beltram Rd

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Bunting Road Chestertown, MD MLS# MDKE2004758
$10,000
Studio

Beds

0.0

Baths

Bunting Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Towhee Road Chestertown, MD MLS# MDKE2004882
$10,000
Studio

Beds

0.0

Baths

Towhee Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
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 Clarissa Road Chestertown, MD MLS# MDKE2005786
$10,000
Studio

Beds

0.0

Baths

Clarissa Road

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View LOTS 253-254 Carimon Road Chestertown, MD MLS# MDKE2003110
$9,500
Studio

Beds

0.0

Baths

LOTS 253-254 Carimon Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Buck Neck Landing Road Chestertown, MD MLS# MDKE2004072
$9,500
Studio

Beds

0.0

Baths

Buck Neck Landing Road

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
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 Sandpiper Road Chestertown, MD MLS# MDKE2005542
$9,000
Studio

Beds

0.0

Baths

Sandpiper Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Lot 24 & 25 Buck Neck Road Chestertown, MD MLS# MDKE2004828
$8,000
Studio

Beds

0.0

Baths

Lot 24 & 25 Buck Neck Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Lenapah Rd Chestertown, MD MLS# MDKE2005184
$8,000
Studio

Beds

0.0

Baths

Lenapah Rd

Chestertown, MD

Bright
Courtesy of COMPASS

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

120

Estimated median home price

$320,000
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 - 100K37
$100K - 200K10
$200K - 300K11
$300K - 400K14
$400K - 500K11
$500K - 600K5
$600K - 700K8
$700K - 800K4
$800K - 900K6
$900K - 1M0
$1M - Max14

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family49
Townhouse9
Condo9
Commercial6
Rental4
Lots and Land44
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms1

(Data as of 11/11/2025)

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.

© 2025 BrightMLS. All Rights Reserved.