View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$475,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 21111 Texas Avenue Chestertown, MD MLS# MDKE2005932
$370,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

21111 Texas Avenue

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS SELECT REALTORS OF EASTON
View 108 Flying Cloud Drive Chestertown, MD MLS# MDKE2005928
$375,000
4

Beds

2.1

Baths

1,936

Sq.Ft.

108 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Georgetown Road Chestertown, MD MLS# MDKE2005844
  • Recently Listed
1 of 7
$89,500
Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 7521 Pine Avenue Chestertown, MD MLS# MDKE2005920
  • Recently Listed
1 of 24
$265,000
3

Beds

1.0

Baths

1,040

Sq.Ft.

7521 Pine Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
$299,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 204 Rolling Road Chestertown, MD MLS# MDKE2005896
    1 of 40
    OPEN HOUSE: Saturday 12/13 11:00 AM - 1:00 PM
    $370,000
    3

    Beds

    2.0

    Baths

    2,296

    Sq.Ft.

    204 Rolling Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 112 Silver Heel Drive Chestertown, MD MLS# MDKE2005880
    $369,900
    5

    Beds

    3.1

    Baths

    2,615

    Sq.Ft.

    112 Silver Heel Drive

    Chestertown, MD

    Bright
    Courtesy of EXP REALTY, LLC
    View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
    $470,000
    4

    Beds

    2.0

    Baths

    1,656

    Sq.Ft.

    222 Mount Vernon Avenue

    Chestertown, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View 304 Hadaway Drive Chestertown, MD MLS# MDKE2005848
    $399,000
    4

    Beds

    2.0

    Baths

    1,325

    Sq.Ft.

    304 Hadaway Drive

    Chestertown, MD

    Bright
    Courtesy of CUMMINGS & CO. REALTORS
    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 109 S College Avenue Chestertown, MD MLS# MDKE2005818
    $449,900
    3

    Beds

    2.1

    Baths

    1,216

    Sq.Ft.

    109 S College Avenue

    Chestertown, MD

    Bright
    Courtesy of CROSS STREET REALTORS LLC
    View 303 E Campus Avenue Chestertown, MD MLS# MDKE2005756
    $363,000
    3

    Beds

    2.0

    Baths

    1,532

    Sq.Ft.

    303 E Campus Avenue

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 318 Lincoln Chestertown, MD MLS# MDKE2005842
      1 of 21
      OPEN HOUSE: Saturday 12/13 12:00 PM - 3:00 PM
      $269,000
      3

      Beds

      2.0

      Baths

      960

      Sq.Ft.

      318 Lincoln

      Chestertown, MD

      Bright
      Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
      View 8750 Georgetown Road Chestertown, MD MLS# MDKE2005834
      $339,000
      3

      Beds

      2.0

      Baths

      1,900

      Sq.Ft.

      8750 Georgetown Road

      Chestertown, MD

      Bright
      Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
      View 411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824
      $419,000
      3

      Beds

      2.1

      Baths

      1,676

      Sq.Ft.

      411 Greenwood Avenue

      Chestertown, MD

      Bright
      Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
      View 101 Birch Run Road Chestertown, MD MLS# MDKE2005810
      $499,999
      3

      Beds

      2.0

      Baths

      1,961

      Sq.Ft.

      101 Birch Run Road

      Chestertown, MD

      Bright
      Courtesy of REMAX VISION
      View Clarissa Road Chestertown, MD MLS# MDKE2005786
      $10,000
      Studio

      Beds

      0.0

      Baths

      Clarissa Road

      Chestertown, MD

      Bright
      Courtesy of SAMSON PROPERTIES
      View 107 Malone Avenue Chestertown, MD MLS# MDKE2005764
      $290,000
      3

      Beds

      1.0

      Baths

      1,200

      Sq.Ft.

      107 Malone Avenue

      Chestertown, MD

      Bright
      Courtesy of DOUGLAS REALTY LLC
      View 8833 Georgetown Road Chestertown, MD MLS# MDKE2005766
      $364,000
      4

      Beds

      2.0

      Baths

      1,625

      Sq.Ft.

      8833 Georgetown 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

      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.