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    142 Properties
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    142 Properties Available

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    The average price in the selected areas has remained stable. Learn more
    • 24607 CHESTERTOWN RD, Chestertown, MD 21620
      3 Beds3 Baths2,294 SqFt
      1/28 28
      Open 6/14 10AM-12PM

      $375,000

      24607 CHESTERTOWN RD, Chestertown, MD 21620

      MLS# MDKE2005240

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 21082 WYOMING AVE, Chestertown, MD 21620
      3 Beds4 Baths2,699 SqFt
      1/63 63
      Open Sat 11AM-2PM

      $1,550,000

      21082 WYOMING AVE, Chestertown, MD 21620

      MLS# MDKE2005016

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 26875 MALLARD RD, Chestertown, MD 21620
      3 Beds4 Baths3,789 SqFt
      1/38 38
      New

      $1,495,000

      26875 MALLARD RD, Chestertown, MD 21620

      MLS# MDKE2005186

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 213 N QUEEN ST, Chestertown, MD 21620
      2 Beds3 Baths1,945 SqFt
      1/49 49
      New

      $638,750

      213 N QUEEN ST, Chestertown, MD 21620

      MLS# MDKE2005210

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 305 WASHINGTON AVE, Chestertown, MD 21620
      5 Beds3 Baths2,476 SqFt
      Coming Soon

      $549,000

      305 WASHINGTON AVE, Chestertown, MD 21620

      MLS# MDKE2005236

      Listed by Select Land & Homes, LLC

      Bright MLS (BMLS)
    • 22570 BAY SHORE RD, Chestertown, MD 21620
      3 Beds2 Baths1,788 SqFt
      1/2 2
      Coming Soon

      $450,000

      22570 BAY SHORE RD, Chestertown, MD 21620

      MLS# MDKE2005230

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 310 HILLTOP LN, Chestertown, MD 21620
      3 Beds3 Baths1,216 SqFt
      1/18 18
      New

      $205,000

      310 HILLTOP LN, Chestertown, MD 21620

      MLS# MDKE2005194

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 10670 TINTAH RD, Chestertown, MD 21620
      3 Beds2 Baths1,404 SqFt
      1/29 29
      New

      $315,000

      10670 TINTAH RD, Chestertown, MD 21620

      MLS# MDKE2005200

      Listed by Samson Properties

      Bright MLS (BMLS)
    • 811 S MEADOWVIEW DR, Chestertown, MD 21620
      3 Beds2 Baths2,064 SqFt
      3D
      Pending

      $459,000

      811 S MEADOWVIEW DR, Chestertown, MD 21620

      MLS# MDKE2005086

      Listed by Redfin Corp

      Bright MLS (BMLS)
    • 420 CANNON ST, Chestertown, MD 21620
      2 Beds2 Baths1,080 SqFt
      1/32 32
      Active

      $395,000

      420 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2005174

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 107 N QUEEN ST, Chestertown, MD 21620
      4 Beds2 Baths3,050 SqFt
      Pending

      $529,000

      107 N QUEEN ST, Chestertown, MD 21620

      MLS# MDKE2005108

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 222 MOUNT VERNON AVE, Chestertown, MD 21620
      4 Beds2 Baths1,656 SqFt
      1/3 3
      Coming Soon

      $375,000

      222 MOUNT VERNON AVE, Chestertown, MD 21620

      MLS# MDKE2005188

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 508 CANNON ST, Chestertown, MD 21620
      3 Beds3 Baths2,240 SqFt
      1/20 20
      Pending

      $150,000

      508 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2005160

      Listed by Coldwell Banker Realty

      Bright MLS (BMLS)
    • 200 HOFFMAN LN, Chestertown, MD 21620
      3 Beds1 Bath1,128 SqFt
      1/8 8
      Under Contract

      $408,000

      200 HOFFMAN LN, Chestertown, MD 21620

      MLS# MDQA2013020

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 109 EDMORE RD, Chestertown, MD 21620
      3 Beds2 Baths1,344 SqFt
      1/24 24
      Active

      $344,900

      109 EDMORE RD, Chestertown, MD 21620

      MLS# MDQA2013256

      Listed by Benson & Mangold, LLC

      Bright MLS (BMLS)
    • 7961 QUAKER NECK RD, Chestertown, MD 21620
      5 Beds4 Baths4,167 SqFt
      1/95 95
      Pending

      $1,495,000

      7961 QUAKER NECK RD, Chestertown, MD 21620

      MLS# MDKE2005090

      Listed by Compass

      Bright MLS (BMLS)
    • 619 CANNON ST, Chestertown, MD 21620
      1 Bed1 Bath882 SqFt
      1/9 9
      Under Contract

      $220,000

      619 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2005050

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 9050 POINT LN, Chestertown, MD 21620
      4 Beds3 Baths3,166 SqFt
      1/71 71
      Under Contract

      $745,000

      9050 POINT LN, Chestertown, MD 21620

      MLS# MDKE2005102

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 10175 JOHN CARVILL RD, Chestertown, MD 21620
      5 Beds4 Baths3,155 SqFt
      1/72 72
      Under Contract

      $625,000

      10175 JOHN CARVILL RD, Chestertown, MD 21620

      MLS# MDKE2005144

      Listed by Select Land & Homes, LLC

      Bright MLS (BMLS)
    • 1814 PONDTOWN RD, Chestertown, MD 21620
      3 Beds1 Bath973 SqFt
      1/8 8
      Pending

      $95,000

      1814 PONDTOWN RD, Chestertown, MD 21620

      MLS# MDQA2013018

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 325 DEVON DR, Chestertown, MD 21620
      4 Beds3 Baths4,086 SqFt
      1/61 61
      Pending

      $525,000

      325 DEVON DR, Chestertown, MD 21620

      MLS# MDKE2005100

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • 10141 FLATLAND RD, Chestertown, MD 21620
      2 Beds1 Bath2,142 SqFt
      1/5 5
      Under Contract

      $292,900

      10141 FLATLAND RD, Chestertown, MD 21620

      MLS# MDKE2005136

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 236 MERGANSER DR, Chestertown, MD 21620
      1 Bed1 Bath900 SqFt
      1/10 10
      Active

      $213,000

      236 MERGANSER DR, Chestertown, MD 21620

      MLS# MDQA2013084

      Listed by Thurston Wyatt Real Estate, LLC

      Bright MLS (BMLS)
    • 25285 FOXCHASE DR, Chestertown, MD 21620
      3 Beds3 Baths2,010 SqFt
      1/39 39
      Pending

      $575,000

      25285 FOXCHASE DR, Chestertown, MD 21620

      MLS# MDKE2005078

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
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    Olson Realty

    Nick Padilla RS- RS-0024607

    +1(302) 535-7785 nick@delawarerealty.net

    614 N DuPont Highway Suite 300, Dover, DE, 19901

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        Home
        Buy
        1. All Listings
        2. Featured Listings
        3. Sold Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        About
        1. About Us
        2. Contact Us
        3. Reviews
        Market Snapshot
    Olson Realty

    Nick Padilla RS- RS-0024607

    +1(302) 535-7785 nick@delawarerealty.net

    614 N DuPont Highway Suite 300, Dover, DE, 19901

    Get My App

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

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

    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.