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    15 Properties
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    15 Properties Available

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    • Newest Listings
    • Beds (Most)
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    The average price in the selected areas has remained stable. Learn more
    • 105 HIGH ST, Chestertown, MD 21620
      5 Beds5 Baths3,243 SqFt
      1/52 52
      Open Sun 11AM-1PM

      $1,395,500

      105 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005002

      Listed by Coldwell Banker Chesapeake Real Estate Company

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

      $638,750

      213 N QUEEN ST, Chestertown, MD 21620

      MLS# MDKE2005210

      Listed by Doug Ashley Realtors, LLC

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

      $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
      1/63 63
      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)
    • 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)
    • 129 N QUEEN ST N, Chestertown, MD 21620
      3 Beds3 Baths2,296 SqFt
      1/38 38
      Under Contract

      $598,500

      129 N QUEEN ST N, Chestertown, MD 21620

      MLS# MDKE2004970

      Listed by Select Land & Homes, LLC

      Bright MLS (BMLS)
    • 226 S WATER ST, Chestertown, MD 21620
      3 Beds4 Baths3,782 Sqft Lot
      1/22 22
      Active

      $998,000

      226 S WATER ST, Chestertown, MD 21620

      MLS# MDKE2004940

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 349 HIGH ST, Chestertown, MD 21620
      7 Beds4 Baths3,664 SqFt
      1/33 33
      Price Dropped by $30K

      $395,000

      349 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2004076

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 117 WATER ST N #2A, Chestertown, MD 21620
      2 Beds1 Bath787 SqFt
      1/28 28
      Active

      $399,000

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

      MLS# MDKE2003742

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 117 N WATER ST N #3B, Chestertown, MD 21620
      1 Bed1 Bath652 SqFt
      1/24 24
      Price Dropped by $48K

      $299,900

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

      MLS# MDKE2003722

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 228 S WATER ST, Chestertown, MD 21620
      3 Beds4 Baths2,592 Sqft Lot
      1/23 23
      Price Dropped by $52K

      $898,000

      228 S WATER ST, Chestertown, MD 21620

      MLS# MDKE2001612

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 511 CANNON ST, Chestertown, MD 21620
      4 Beds2 Baths1,106 SqFt
      1/11 11
      New

      $1,850

      511 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2005190

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 206 CANNON ST, Chestertown, MD 21620
      1.56 Acres
      1/9 9
      Price Dropped by $100K

      $1,150,000

      206 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2003620

      Listed by Benson & Mangold, LLC

      Bright MLS (BMLS)
    • 1
    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.

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    Logo - Broker (White) (7)Fusion

    Pearson Smith Realty, LLC.

    David A. Caceres Lic# 5001684

    +1(240) 266-0144 david@thelifeindc.com

    43777 Central Station Dr Ste 390 Ashburn VA 20147

    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.

    SITE MAP

        Home
        My Listings
        1. Featured Listings
        2. Sold Listings
        Communities
        1. Rockville
        2. Ashburn
        3. Belmont
        Sell My Home
        Services
        Resources
        1. Affordability Calculator
        2. Mortgage Calculator
        3. Market Snapshot
        4. iBuyer Guide
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
    Logo - Broker (White) (7)Fusion

    Pearson Smith Realty, LLC.

    David A. Caceres Lic# 5001684

    +1(240) 266-0144 david@thelifeindc.com

    43777 Central Station Dr Ste 390 Ashburn VA 20147

    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