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    130 Properties

    130 Properties Available

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    • 110 FLYING CLOUD COURT, Chestertown, MD 21620
      1/20 20
      Active

      $ 349,900

      3 Beds3 Baths1,856 SqFt

      110 FLYING CLOUD COURT, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004850

      Listed by Berkshire Hathaway HomeServices Homesale Realty

      Bright MLS (BMLS)
    • 10578 TONOPAH RD, Chestertown, MD 21620
      1/19 19
      Under Contract

      $ 329,900

      3 Beds3 Baths0.35 Acres Lot

      10578 TONOPAH RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004894

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 23620 LANDS END RD, Chestertown, MD 21620
      1/66 66
      Under Contract

      $ 5,500,000

      5 Beds8 Baths9,852 SqFt

      23620 LANDS END RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004760

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 10705 MILLBROOK DR, Chestertown, MD 21620
      1/43 43
      Pending

      $ 305,000

      4 Beds3 Baths2,106 SqFt

      10705 MILLBROOK DR, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004846

      Listed by EXP Realty, LLC

      Bright MLS (BMLS)
    • 109 WILTON RD, Chestertown, MD 21620
      1/30 30
      Active

      $ 349,900

      3 Beds2 Baths1,392 SqFt

      109 WILTON RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDQA2011782

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 23315 SANDPIPER RD, Chestertown, MD 21620
      1/37 37
      Under Contract

      $ 309,000

      2 Beds2 Baths1,272 SqFt

      23315 SANDPIPER RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004728

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 107 DUTCHESS RD, Chestertown, MD 21620
      1/15 15
      Active

      $ 335,000

      3 Beds2 Baths1,380 SqFt

      107 DUTCHESS RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDQA2011746

      Listed by The Hogans Agency

      Bright MLS (BMLS)
    • 100 ACORN DR, Chestertown, MD 21620
      1/27 27
      Under Contract

      $ 285,000

      3 Beds3 Baths1,930 SqFt

      100 ACORN DR, Chestertown, MD 21620

      Townhouse

      MLS# MDKE2004566

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 24543 CHESTERTOWN RD, Chestertown, MD 21620
      1/55 55
      Pending

      $ 475,000

      3 Beds2 Baths3,280 SqFt

      24543 CHESTERTOWN RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004580

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 26865 MALLARD RD, Chestertown, MD 21620
      1/49 49
      Price Dropped by $49K

      $ 950,000

      4 Beds3 Baths3,355 SqFt

      26865 MALLARD RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2004550

      Listed by TTR Sotheby's International Realty

      Bright MLS (BMLS)
    • 23393 CACAWAY FARM LN, Chestertown, MD 21620
      1/44 44
      Active

      $ 1,450,000

      3 Beds4 Baths4,446 SqFt

      23393 CACAWAY FARM LN, Chestertown, MD 21620

      Condo

      MLS# MDKE2004002

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 116 PINE CHIP RD, Chestertown, MD 21620
      1/35 35
      Active

      $ 515,000

      3 Beds2 Baths2,767 SqFt

      116 PINE CHIP RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDQA2010882

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 117 N WATER ST #1A, Chestertown, MD 21620
      1/28 28
      Active

      $ 725,000

      3 Beds3 Baths

      117 N WATER ST #1A, Chestertown, MD 21620

      Single Family Home, Condo

      MLS# MDKE2004206

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 349 HIGH ST, Chestertown, MD 21620
      1/33 33
      Price Dropped by $30K

      $ 395,000

      7 Beds4 Baths3,664 SqFt

      349 HIGH ST, Chestertown, MD 21620

      Townhouse

      MLS# MDKE2004076

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 117 WATER ST N #2A, Chestertown, MD 21620
      1/28 28
      Active

      $ 399,000

      2 Beds1 Bath787 SqFt

      117 WATER ST N #2A, Chestertown, MD 21620

      Condo

      MLS# MDKE2003742

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 117 N WATER ST N #3B, Chestertown, MD 21620
      1/24 24
      Price Dropped by $48K

      $ 299,900

      1 Bed1 Bath652 SqFt

      117 N WATER ST N #3B, Chestertown, MD 21620

      Condo

      MLS# MDKE2003722

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 228 S WATER ST, Chestertown, MD 21620
      1/23 23
      Active

      $ 950,000

      3 Beds4 Baths2,592 Sqft Lot

      228 S WATER ST, Chestertown, MD 21620

      Townhouse

      MLS# MDKE2001612

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 116 METCALF RD, Chestertown, MD 21620
      1/7 7
      New

      $ 2,350

      3 Beds2 Baths1,140 SqFt

      116 METCALF RD, Chestertown, MD 21620

      Single Family Home

      MLS# MDKE2005168

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 329 HIGH ST, Chestertown, MD 21620
      1/3 3
      Under Contract

      $ 1,200,000

      4,500 SqFt

      329 HIGH ST, Chestertown, MD 21620

      Commercial

      MLS# MDKE2005172

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • CROMWELL CLARK RD, Chestertown, MD 21620
      1/19 19
      New

      $ 3,000,000

      87.34 Acres

      CROMWELL CLARK RD, Chestertown, MD 21620

      Vacant Land

      MLS# MDKE2005156

      Listed by The Land Group

      Bright MLS (BMLS)
    • 9020 GEORGETOWN RD, Chestertown, MD 21620
      1/10 10
      Active

      $ 80,000

      2.36 Acres

      9020 GEORGETOWN RD, Chestertown, MD 21620

      Vacant Land

      MLS# MDKE2005152

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 22671 WOOD YARD LN, Chestertown, MD 21620
      1/4 4
      Pending

      $ 15,000

      0.48 Acres

      22671 WOOD YARD LN, Chestertown, MD 21620

      Vacant Land

      MLS# MDKE2005122

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • CAULKS FIELD ROAD, Chestertown, MD 21620
      1/3 3
      Active

      $ 150,000

      2 Acres

      CAULKS FIELD ROAD, Chestertown, MD 21620

      Vacant Land

      MLS# MDKE2005120

      Listed by RE/MAX Allegiance

      Bright MLS (BMLS)
    • GEORGETOWN RD SE, Chestertown, MD 21620
      1/2 2
      Active

      $ 150,000

      2 Acres

      GEORGETOWN RD SE, Chestertown, MD 21620

      Vacant Land

      MLS# MDKE2005076

      Listed by RE/MAX Allegiance

      Bright MLS (BMLS)
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    eXp Realty

    Lindsey Jones

    +1(267) 342-0316 [email protected]

    Abington Twp, PA, 19001, USA
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    exp-world-white
    eXp Realty

    Lindsey Jones

    +1(267) 342-0316 [email protected]

    Abington Twp, PA, 19001, USA
      • Home
        About
        1. About Us
        2. Contact Us
        3. Reviews
      • Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Market Snapshot
      • Sell
        1. Sell My Home
        2. Home Valuation

    Get My App

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

    IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.