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    136 Properties
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    136 Properties Available

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    • Newest Listings
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    The average price in the selected areas has remained stable. Learn more
    • 24095 CHESTERTOWN RD, Chestertown, MD 21620
      3 Beds1 Bath1,104 SqFt
      1/45 45
      Under Contract

      $310,000

      24095 CHESTERTOWN RD, Chestertown, MD 21620

      MLS# MDKE2005020

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 5179 QUAKER NECK RD, Chestertown, MD 21620
      1 Bed1 Bath1,148 SqFt
      1/48 48
      Active

      $559,900

      5179 QUAKER NECK RD, Chestertown, MD 21620

      MLS# MDKE2005028

      Listed by Hyatt & Company Real Estate, LLC

      Bright MLS (BMLS)
    • LITTLE HARBOR WAY #1, Chestertown, MD 21620
      3 Beds3 Baths2,315 SqFt
      1/22 22
      Active

      $1,459,000

      LITTLE HARBOR WAY #1, Chestertown, MD 21620

      MLS# MDKE2004992

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 114 DARDEN RD, Chestertown, MD 21620
      3 Beds1 Bath1,056 SqFt
      1/33 33
      Pending

      $269,900

      114 DARDEN RD, Chestertown, MD 21620

      MLS# MDQA2012808

      Listed by FSBO Broker

      Bright MLS (BMLS)
    • 300 HILLTOP LN, Chestertown, MD 21620
      3 Beds3 Baths1,200 SqFt
      1/20 20
      Active

      $220,000

      300 HILLTOP LN, Chestertown, MD 21620

      MLS# MDKE2005004

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 105 HIGH ST, Chestertown, MD 21620
      5 Beds5 Baths3,243 SqFt
      1/52 52
      Active

      $1,395,500

      105 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005002

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 103 LANDING LN, Chestertown, MD 21620
      2 Beds3 Baths2,100 SqFt
      1/41 41
      Active

      $569,000

      103 LANDING LN, Chestertown, MD 21620

      MLS# MDKE2004972

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 128 EDMORE RD, Chestertown, MD 21620
      4 Beds2 Baths2,568 SqFt
      1/59 59
      Price Dropped by $10K

      $415,000

      128 EDMORE RD, Chestertown, MD 21620

      MLS# MDQA2012546

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      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)
    • 110 FLYING CLOUD COURT, Chestertown, MD 21620
      3 Beds3 Baths1,856 SqFt
      1/17 17
      Under Contract

      $349,900

      110 FLYING CLOUD COURT, Chestertown, MD 21620

      MLS# MDKE2004850

      Listed by Berkshire Hathaway HomeServices Homesale Realty

      Bright MLS (BMLS)
    • 23620 LANDS END RD, Chestertown, MD 21620
      5 Beds8 Baths9,852 SqFt
      1/77 77
      Price Dropped by $650K

      $4,850,000

      23620 LANDS END RD, Chestertown, MD 21620

      MLS# MDKE2004760

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 212 LANDING LN, Chestertown, MD 21620
      3 Beds4 Baths
      1/36 36
      Active

      $759,000

      212 LANDING LN, Chestertown, MD 21620

      MLS# MDKE2004782

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 109 WILTON RD, Chestertown, MD 21620
      3 Beds2 Baths1,392 SqFt
      1/30 30
      Active

      $349,900

      109 WILTON RD, Chestertown, MD 21620

      MLS# MDQA2011782

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 11040 KYLIE LN, Chestertown, MD 21620
      4 Beds4 Baths3,684 SqFt
      1/67 67
      Active

      $659,000

      11040 KYLIE LN, Chestertown, MD 21620

      MLS# MDKE2004586

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 24543 CHESTERTOWN RD, Chestertown, MD 21620
      3 Beds2 Baths3,280 SqFt
      1/55 55
      Price Dropped by $50K

      $425,000

      24543 CHESTERTOWN RD, Chestertown, MD 21620

      MLS# MDKE2004580

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 23393 CACAWAY FARM LN, Chestertown, MD 21620
      3 Beds4 Baths4,446 SqFt
      1/45 45
      Price Dropped by $100K

      $1,250,000

      23393 CACAWAY FARM LN, Chestertown, MD 21620

      MLS# MDKE2004002

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 116 PINE CHIP RD, Chestertown, MD 21620
      3 Beds2 Baths2,767 SqFt
      1/35 35
      Active

      $495,000

      116 PINE CHIP RD, Chestertown, MD 21620

      MLS# MDQA2010882

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 117 N WATER ST #1A, Chestertown, MD 21620
      3 Beds3 Baths
      1/28 28
      Active

      $725,000

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

      MLS# MDKE2004206

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 349 HIGH ST, Chestertown, MD 21620
      7 Beds4 Baths3,664 SqFt
      1/33 33
      Active

      $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)
    • TONOPAH RD., Chestertown, MD 21620
      0.34 Acres
      1/2 2
      New

      $40,000

      TONOPAH RD., Chestertown, MD 21620

      MLS# MDKE2005564

      Listed by The Hogans Agency

      Bright MLS (BMLS)
    • JOHNSONTOWN RD, Chestertown, MD 21620
      0.9 Acres
      1/6 6
      New

      $35,000

      JOHNSONTOWN RD, Chestertown, MD 21620

      MLS# MDKE2005550

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • SANDPIPER RD, Chestertown, MD 21620
      0.61 Acres
      1/2 2
      Active

      $9,000

      SANDPIPER RD, Chestertown, MD 21620

      MLS# MDKE2005542

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • ELM RD, Chestertown, MD 21620
      0.22 Acres
      1/2 2
      Under Contract

      $12,675

      ELM RD, Chestertown, MD 21620

      MLS# MDKE2005532

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
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    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