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    147 Properties
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    147 Properties Available

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    The average price in the selected areas has remained stable. Learn more
    • 5179 QUAKER NECK RD, Chestertown, MD 21620
      1 Bed1 Bath1,148 SqFt
      1/48 48
      Under Contract

      $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
      4 Beds4 Baths3,540 SqFt
      1/27 27
      Active

      $1,800,000

      LITTLE HARBOR WAY #1, Chestertown, MD 21620

      MLS# MDKE2004992

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 128 EDMORE RD, Chestertown, MD 21620
      4 Beds2 Baths2,568 SqFt
      1/59 59
      Under Contract

      $415,000

      128 EDMORE RD, Chestertown, MD 21620

      MLS# MDQA2012546

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • 23620 LANDS END RD, Chestertown, MD 21620
      5 Beds8 Baths9,852 SqFt
      1/77 77
      Pending

      $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
      Under Contract

      $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
      1/69 69
      Price Dropped by $10K

      $649,000

      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
      Pending

      $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
      Pending

      $1,195,000

      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

      $475,000

      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
      Under Contract

      $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)
    • CLARISSA RD, Chestertown, MD 21620
      0.34 Acres
      Price Dropped by $5K

      $10,000

      CLARISSA RD, Chestertown, MD 21620

      MLS# MDKE2005786

      Listed by Samson Properties

      Bright MLS (BMLS)
    • 404 SPRING RD, Chestertown, MD 21620
      0.99 Acres
      1/11 11
      Active

      $19,500

      404 SPRING RD, Chestertown, MD 21620

      MLS# MDQA2014990

      Listed by The Parker Group

      Bright MLS (BMLS)
    • 517 HIGH ST, Chestertown, MD 21620
      1,728 SqFt
      1/51 51
      Active

      $389,900

      517 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005736

      Listed by L. C. Parker Real Estate

      Bright MLS (BMLS)
    • FAIRLEE-MELITOTA RD, Chestertown, MD 21620
      0.5 Acres
      1/4 4
      Coming Soon

      $50,000

      FAIRLEE-MELITOTA RD, Chestertown, MD 21620

      MLS# MDKE2005726

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 109 2ND ST, Chestertown, MD 21620
      1.8 Acres
      1/9 9
      Active

      $15,000

      109 2ND ST, Chestertown, MD 21620

      MLS# MDQA2014918

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • 23628 CANVASBACK RD, Chestertown, MD 21620
      0.34 Acres
      1/5 5
      Under Contract

      $15,000

      23628 CANVASBACK RD, Chestertown, MD 21620

      MLS# MDKE2005696

      Listed by Gunther-McClary Real Estate

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

      $15,000

      ELBON RD, Chestertown, MD 21620

      MLS# MDKE2005656

      Listed by Signature Home Realty LLC

      Bright MLS (BMLS)
    • BUCK NECK LANDING RD, Chestertown, MD 21620
      0.55 Acres
      1/2 2
      Active

      $10,000

      BUCK NECK LANDING RD, Chestertown, MD 21620

      MLS# MDKE2005586

      Listed by Rosendale Realty

      Bright MLS (BMLS)
    • TONOPAH RD., Chestertown, MD 21620
      0.34 Acres
      1/2 2
      Active

      $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
      1/16 16
      Active

      $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)
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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.

    SITE MAP

        Home
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        About
        1. My Story
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        Home Valuation
        Did You Hear About Your Neighbor
    VA305_primary_cabProud Partner of FGP

    Berkshire Hathaway HomeServices PenFed Realty

    Jared Schwartz Lic# 5012305

    +1(301) 906-5301 jared.schwartz@penfedrealty.com

    1997 Annapolis Exchange Pkwy 101, Annapolis, MD, 21401, USA

    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
        3. Property Portfolio
        Communities
        1. Annapolis
        2. Severna Park
        3. Arnold
        Sell My Home
        Services
        Resources
        1. Affordability Calculator
        2. Mortgage Calculator
        3. Market Snapshot
        About
        1. My Story
        2. My Resume
        3. Client Survey
        4. Testimonials
        5. Contact Me
        Home Valuation
        Did You Hear About Your Neighbor
    VA305_primary_cabProud Partner of FGP

    Berkshire Hathaway HomeServices PenFed Realty

    Jared Schwartz Lic# 5012305

    +1(301) 906-5301 jared.schwartz@penfedrealty.com

    1997 Annapolis Exchange Pkwy 101, Annapolis, MD, 21401, USA

    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