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City Overview

Chestertown, MD

Median List Price
$380,000
Active Listings
74

Market

Chestertown market snapshot

Median price
$380,000
Active listings
74
Avg. days on market
89
Price / sq ft
$256

Current Listing Inventory for Chestertown, MD

Inventory is continuously updated — select a category to view current listings.

Active listings by price range

Number of active listings in Chestertown, MD by price range
Price RangeListings
Under $200K2
$200K-$400K37
$400K-$600K10
$600K-$800K9
$800K-$1M7
Over $1M9

Explore

Explore Chestertown, MD

For sale

Available homes in Chestertown

  • Active
    39 photos

    $675,000

    5 bd, 3 ba, 2,838 Sq Ft

    212 Washington AvenueChestertown, MD 21620#MDKE2007016

    Single Family Residence
  • Active
    3 photos

    $85,000

    2 bd, 1 ba, 1,296 Sq Ft

    234 N College AvenueChestertown, MD 21620#MDKE2006670

    Single Family Residence
  • For Rent
    10 photos

    $1,450/mo

    1 bd, 1 ba, 900 Sq Ft

    128 N Queen Street Unit 3Chestertown, MD 21620#MDKE2006574

    Single Family Residence
  • Active
    39 photos

    $1,300,000

    3 ba, 3,740 Sq Ft

    327 Cannon StreetChestertown, MD 21620#MDKE2006104

    Mixed Use
  • Active
    92 photos

    $829,000

    3 bd, 3.5 ba, 2,472 Sq Ft

    106 Queen StreetChestertown, MD 21620#MDKE2006152

    Single Family Residence
  • Active
    1 photos

    $359,000

    2 bd, 1.5 ba, 1,036 Sq Ft

    101 S College AvenueChestertown, MD 21620#MDKE2006918

    Single Family Residence
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which EXIT Realty participates, and is provided by BRIGHT through a licensing agreement. 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 closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright ©2026 Bright MLS. All rights reserved.

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