View 7488 Poplar Avenue Chestertown, MD MLS# MDKE2003902
$250,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

7488 Poplar Avenue

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 208 Byford Drive Chestertown, MD MLS# MDKE2003778
    1 of 44
    OPEN HOUSE: Saturday 5/4 11:00 AM - 2:00 PM
    $385,000
    3

    Beds

    2.1

    Baths

    2,045

    Sq.Ft.

    208 Byford Drive

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View Kinglet Road Chestertown, MD MLS# MDKE2003904
    • Recently Listed
    1 of 6
    $9,500
    Studio

    Beds

    0.0

    Baths

    Kinglet Road

    Chestertown, MD

    Bright
    Courtesy of CROSS STREET REALTORS LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View Parcel Buck Neck Ldg Road Chestertown, MD MLS# MDKE2003874
    $15,000
    Studio

    Beds

    0.0

    Baths

    Parcel Buck Neck Ldg Road

    Chestertown, MD

    Bright
    Courtesy of ASHLAND AUCTION GROUP LLC
    View 214 Richard Drive Chestertown, MD MLS# MDKE2003860
    $385,000
    2

    Beds

    2.1

    Baths

    1,723

    Sq.Ft.

    214 Richard Drive

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View Sandpiper Road Chestertown, MD MLS# MDKE2003870
    • Recently Listed
    1 of 2
    $15,000
    Studio

    Beds

    0.0

    Baths

    Sandpiper Road

    Chestertown, MD

    Bright
    Courtesy of ASHLAND AUCTION GROUP LLC
    View Buck Neck Rd Chestertown, MD MLS# MDKE2003864
    • Recently Listed
    1 of 2
    $12,500
    Studio

    Beds

    0.0

    Baths

    Buck Neck Rd

    Chestertown, MD

    Bright
    Courtesy of SELECT LAND & HOMES, LLC
    View 23060 Old Fairlee Road Chestertown, MD MLS# MDKE2003798
    $70,000
    Studio

    Beds

    0.0

    Baths

    1,040

    Sq.Ft.

    23060 Old Fairlee Road

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 21345 Persimmon Drive Chestertown, MD MLS# MDKE2003862
    $158,000
    2

    Beds

    1.0

    Baths

    1,232

    Sq.Ft.

    21345 Persimmon Drive

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View 117 N Water Street N # 3B Chestertown, MD MLS# MDKE2003722
      1 of 24
      OPEN HOUSE: Saturday 5/4 1:00 PM - 3:00 PM
      $385,000
      1

      Beds

      1.0

      Baths

      652

      Sq.Ft.

      117 N Water Street N # 3B

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 117 N Water Street # 3A Chestertown, MD MLS# MDKE2003730
      $395,000
      2

      Beds

      1.0

      Baths

      729

      Sq.Ft.

      117 N Water Street # 3A

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 104 Conley Drive Chestertown, MD MLS# MDKE2003806
      $234,900
      3

      Beds

      1.1

      Baths

      1,280

      Sq.Ft.

      104 Conley Drive

      Chestertown, MD

      Bright
      Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
      View 117 Water Street N # 2B Chestertown, MD MLS# MDKE2003732
      $405,000
      1

      Beds

      1.0

      Baths

      850

      Sq.Ft.

      117 Water Street N # 2B

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 116 Riverside Terrace # 7 Chestertown, MD MLS# MDKE2003790
      $395,000
      2

      Beds

      1.1

      Baths

      900

      Sq.Ft.

      116 Riverside Terrace # 7

      Chestertown, MD

      Bright
      Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
      View 0 Gateway Drive Chestertown, MD MLS# MDKE2003756
      $100,000
      Studio

      Beds

      0.0

      Baths

      0 Gateway Drive

      Chestertown, MD

      Bright
      Courtesy of COTTAGE STREET REALTY LLC
      View 10605 Tonopah Road Chestertown, MD MLS# MDKE2003746
      $299,900
      4

      Beds

      2.0

      Baths

      1,248

      Sq.Ft.

      10605 Tonopah Road

      Chestertown, MD

      Bright
      Courtesy of RE/MAX EXECUTIVE
      View 9062 Fairlee Road Chestertown, MD MLS# MDKE2003724
      $335,500
      3

      Beds

      2.0

      Baths

      1,344

      Sq.Ft.

      9062 Fairlee Road

      Chestertown, MD

      Bright
      Courtesy of TAYLOR PROPERTIES
      View Cloquet Chestertown, MD MLS# MDKE2003654
      $70,000
      Studio

      Beds

      0.0

      Baths

      Cloquet

      Chestertown, MD

      Bright
      Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
      View 5772 Johnsontown Road Chestertown, MD MLS# MDKE2003668
      $350,000
      3

      Beds

      2.0

      Baths

      1,344

      Sq.Ft.

      5772 Johnsontown Road

      Chestertown, MD

      Bright
      Courtesy of CROSS STREET REALTORS LLC
      View 24581 Willow Oak Lane Chestertown, MD MLS# MDKE2003640
      $149,000
      2

      Beds

      2.0

      Baths

      1,352

      Sq.Ft.

      24581 Willow Oak Lane

      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

      86

      Estimated median home price

      $298,450
      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 - 100K33
      $100K - 200K4
      $200K - 300K7
      $300K - 400K9
      $400K - 500K7
      $500K - 600K1
      $600K - 700K2
      $700K - 800K1
      $800K - 900K6
      $900K - 1M5
      $1M - Max11

      Homes for Sale by Type in Chestertown, MD

      Property TypeCount
      Single Family31
      Townhouse7
      Condo5
      Commercial5
      Rental13
      Lots and Land34
      Condo/Town/CoOp0
      CoOp0
      Multi Family3
      Mobile Home0
      Farms1

      (Data as of 4/30/2024)

      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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