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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
    • 303 E CAMPUS AVE, Chestertown, MD 21620
      3 Beds2 Baths1,532 SqFt
      1/32 32
      Coming Soon

      $363,000

      303 E CAMPUS AVE, Chestertown, MD 21620

      MLS# MDKE2005756

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 411 GREENWOOD AVE, Chestertown, MD 21620
      3 Beds3 Baths1,676 SqFt
      1/6 6
      Coming Soon

      $419,000

      411 GREENWOOD AVE, Chestertown, MD 21620

      MLS# MDKE2005824

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 8750 GEORGETOWN RD, Chestertown, MD 21620
      3 Beds2 Baths1,900 SqFt
      1/30 30
      Open 10/25 1PM-3PM

      $339,000

      8750 GEORGETOWN RD, Chestertown, MD 21620

      MLS# MDKE2005834

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 103 LANDING LN, Chestertown, MD 21620
      2 Beds3 Baths2,100 SqFt
      1/69 69
      Open 11/2 11AM-2PM

      $559,000

      103 LANDING LN, Chestertown, MD 21620

      MLS# MDKE2005670

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 200 WASHINGTON AVE, Chestertown, MD 21620
      4 Beds4 Baths2,917 SqFt
      1/35 35
      Open 10/25 10AM-2PM

      $695,000

      200 WASHINGTON AVE, Chestertown, MD 21620

      MLS# MDKE2005538

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 105 HIGH ST, Chestertown, MD 21620
      5 Beds5 Baths3,243 SqFt
      1/52 52
      Open 11/2 11AM-1PM

      $1,395,500

      105 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005002

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 8620 PARK DR, Chestertown, MD 21620
      4 Beds3 Baths2,524 SqFt
      1/53 53
      New

      $499,900

      8620 PARK DR, Chestertown, MD 21620

      MLS# MDKE2005850

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 10121 FAIRLEE RD, Chestertown, MD 21620
      6 Beds5 Baths4,954 SqFt
      1/6 6
      Coming Soon

      $2,350,000

      10121 FAIRLEE RD, Chestertown, MD 21620

      MLS# MDKE2005852

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 7844 CHESTER CT, Chestertown, MD 21620
      4 Beds3 Baths3,248 SqFt
      1/51 51
      New

      $770,000

      7844 CHESTER CT, Chestertown, MD 21620

      MLS# MDKE2005796

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 10781 FERMOY RD, Chestertown, MD 21620
      3 Beds3 Baths2,160 SqFt
      Coming Soon

      $449,900

      10781 FERMOY RD, Chestertown, MD 21620

      MLS# MDKE2005854

      Listed by Real Broker, LLC

      Bright MLS (BMLS)
    • 206 S WATER ST, Chestertown, MD 21620
      4 Beds4 Baths2,008 SqFt
      1/46 46
      New

      $619,000

      206 S WATER ST, Chestertown, MD 21620

      MLS# MDKE2005840

      Listed by TTR Sotheby's International Realty

      Bright MLS (BMLS)
    • 8951 ORCHARD DR, Chestertown, MD 21620
      4 Beds4 Baths3,735 SqFt
      1/12 12
      Coming Soon

      $695,000

      8951 ORCHARD DR, Chestertown, MD 21620

      MLS# MDKE2005836

      Listed by Rock Hall Properties Real Estate

      Bright MLS (BMLS)
    • 222 DUTCHESS RD, Chestertown, MD 21620
      3 Beds2 Baths1,096 SqFt
      1/24 24
      New

      $320,000

      222 DUTCHESS RD, Chestertown, MD 21620

      MLS# MDQA2014830

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 492 PEAR TREE POINT RD, Chestertown, MD 21620
      3 Beds2 Baths2,632 SqFt
      1/73 73
      New

      $920,000

      492 PEAR TREE POINT RD, Chestertown, MD 21620

      MLS# MDQA2015126

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 217 AUSTIN, Centreville, MD 21617
      3 Beds3 Baths2,454 SqFt
      Coming Soon

      $649,900

      217 AUSTIN, Centreville, MD 21617

      MLS# MDQA2015220

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • 318 LINCOLN, Chestertown, MD 21620
      3 Beds2 Baths960 SqFt
      1/5 5
      Coming Soon

      $269,000

      318 LINCOLN, Chestertown, MD 21620

      MLS# MDKE2005842

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 228 S WATER ST, Chestertown, MD 21620
      3 Beds4 Baths2,310 SqFt
      1/29 29
      New

      $878,000

      228 S WATER ST, Chestertown, MD 21620

      MLS# MDKE2005812

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 124 CHAR NOR MANOR BLVD, Chestertown, MD 21620
      2 Beds2 Baths1,024 SqFt
      1/31 31
      Under Contract

      $245,000

      124 CHAR NOR MANOR BLVD, Chestertown, MD 21620

      MLS# MDQA2014812

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 101 BIRCH RUN RD, Chestertown, MD 21620
      3 Beds2 Baths1,961 SqFt
      1/38 38
      Active

      $525,000

      101 BIRCH RUN RD, Chestertown, MD 21620

      MLS# MDKE2005810

      Listed by Remax Vision

      Bright MLS (BMLS)
    • 10050 FORREST LN, Chestertown, MD 21620
      4 Beds2 Baths1,820 SqFt
      1/49 49
      Under Contract

      $899,000

      10050 FORREST LN, Chestertown, MD 21620

      MLS# MDKE2005792

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 127 WOOD DUCK LN, Chestertown, MD 21620
      3 Beds2 Baths1,666 SqFt
      1/26 26
      Active

      $215,000

      127 WOOD DUCK LN, Chestertown, MD 21620

      MLS# MDQA2015154

      Listed by RE/MAX Point Realty

      Bright MLS (BMLS)
    • 206 VALLEY, Chestertown, MD 21620
      4 Beds2 Baths2,869 SqFt
      1/35 35
      Active

      $639,900

      206 VALLEY, Chestertown, MD 21620

      MLS# MDKE2005762

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 107 MALONE AVE, Chestertown, MD 21620
      3 Beds1 Bath1,200 SqFt
      1/27 27
      Price Dropped by $15K

      $290,000

      107 MALONE AVE, Chestertown, MD 21620

      MLS# MDKE2005764

      Listed by Douglas Realty LLC

      Bright MLS (BMLS)
    • 118 LITTLE HARBOR WAY #202, Chestertown, MD 21620
      3 Beds2 Baths1,600 SqFt
      1/19 19
      Coming Soon

      $695,000

      118 LITTLE HARBOR WAY #202, Chestertown, MD 21620

      MLS# MDKE2005800

      Listed by Benson & Mangold, 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.

    SITE MAP

        Home
        My Listings
        1. Featured Listings
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        Communities
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        2. Severna Park
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        Sell My Home
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        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

    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