View 331 Devon Drive Chestertown, MD MLS# MDKE2007134
$499,999
4

Beds

3.1

Baths

3,506

Sq.Ft.

331 Devon Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 896 Washington Avenue Chestertown, MD MLS# MDKE2007140
$325,000
1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 10 Cedar Chase Court Chestertown, MD MLS# MDKE2007124
$495,000
3

Beds

2.1

Baths

1,656

Sq.Ft.

10 Cedar Chase Court

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 6324 Quaker Neck Road Chestertown, MD MLS# MDKE2007098
$2,895,000
5

Beds

3.1

Baths

5,938

Sq.Ft.

6324 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 22974 Bay Shore Road Chestertown, MD MLS# MDKE2007106
  • Recently Listed with Virtual Tour
1 of 22
$329,900
2

Beds

2.0

Baths

1,440

Sq.Ft.

22974 Bay Shore Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 7712 Waterview Lane Chestertown, MD MLS# MDKE2007104
$659,999
3

Beds

2.2

Baths

2,716

Sq.Ft.

7712 Waterview Lane

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 104 Maple Avenue Chestertown, MD MLS# MDKE2007096
  • Recently Listed
1 of 21
$1,050,000
7,296

Sq.Ft.

104 Maple Avenue

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - ANNAPOLIS
View 8732 Elm Road Chestertown, MD MLS# MDKE2007082
  • Recently Listed
1 of 26
OPEN HOUSE: Saturday 10/3 2:00 PM - 3:30 PM
$289,000
3

Beds

2.0

Baths

1,056

Sq.Ft.

8732 Elm Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8276 Broad Neck Road Chestertown, MD MLS# MDKE2007092
$1,295,000
4

Beds

3.1

Baths

3,383

Sq.Ft.

8276 Broad Neck Road

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 223 Mount Vernon Avenue Chestertown, MD MLS# MDKE2007080
$200,000
4

Beds

1.0

Baths

1,816

Sq.Ft.

223 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Address not provided Chestertown, MD MLS# MDKE2007054
$695,000
0.0

Baths

Address not provided

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Towhee Road Chestertown, MD MLS# MDKE2007066
$50,000
0.0

Baths

Towhee Road

Chestertown, MD

Bright
Courtesy of THE PARKER GROUP
View 27942 Old Morgnec Road Chestertown, MD MLS# MDKE2007044
$89,000
0.0

Baths

27942 Old Morgnec Road

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 7415 Wilkins Lane Chestertown, MD MLS# MDKE2007030
$229,000
3

Beds

1.0

Baths

936

Sq.Ft.

7415 Wilkins Lane

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 24775 Langford Road Chestertown, MD MLS# MDKE2007012
$315,000
3

Beds

1.0

Baths

1,008

Sq.Ft.

24775 Langford Road

Chestertown, MD

Bright
Courtesy of RE/MAX CHESAPEAKE
View 104 Lincoln Drive Chestertown, MD MLS# MDKE2007032
$295,000
3

Beds

1.0

Baths

960

Sq.Ft.

104 Lincoln Drive

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 7482 Poplar Avenue Chestertown, MD MLS# MDKE2007042
$275,000
3

Beds

1.0

Baths

975

Sq.Ft.

7482 Poplar Avenue

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 300 and 302 S Mill Street Chestertown, MD MLS# MDKE2007020
$1,195,000
0.0

Baths

300 and 302 S Mill Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 212 Washington Avenue Chestertown, MD MLS# MDKE2007016
    1 of 39
    OPEN HOUSE: Saturday 10/3 10:00 AM - 1:00 PM
    $675,000
    5

    Beds

    3.0

    Baths

    2,838

    Sq.Ft.

    212 Washington Avenue

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 300 and 302 S Mill Street Chestertown, MD MLS# MDKE2006850
    $1,195,000
    2

    Beds

    1.0

    Baths

    806

    Sq.Ft.

    300 and 302 S Mill Street

    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

    129

    Estimated median home price

    $325,000
    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 - 100K34
    $100K - 200K6
    $200K - 300K19
    $300K - 400K20
    $400K - 500K10
    $500K - 600K1
    $600K - 700K5
    $700K - 800K10
    $800K - 900K7
    $900K - 1M0
    $1M - Max17

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family50
    Townhouse6
    Condo15
    Commercial12
    Rental9
    Lots and Land45
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms1

    (Data as of 9/30/2026)

    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.

    © 2026 BrightMLS. All Rights Reserved.