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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
    • 23043 BAY SHORE SPUR, Chestertown, MD 21620
      4 Beds3 Baths2,630 SqFt
      1/27 27
      Price Dropped by $25K

      $350,000

      23043 BAY SHORE SPUR, Chestertown, MD 21620

      MLS# MDKE2005584

      Listed by Rock Hall Properties Real Estate

      Bright MLS (BMLS)
    • 7483 SHORTALL ST, Chestertown, MD 21620
      3 Beds2 Baths1,232 SqFt
      1/26 26
      Pending

      $290,000

      7483 SHORTALL ST, Chestertown, MD 21620

      MLS# MDKE2005616

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 24415 CHESTERTOWN RD, Chestertown, MD 21620
      2 Beds1 Bath1,110 SqFt
      1/29 29
      Pending

      $264,900

      24415 CHESTERTOWN RD, Chestertown, MD 21620

      MLS# MDKE2005630

      Listed by TTR Sotheby's International Realty

      Bright MLS (BMLS)
    • 110 S MILL ST, Chestertown, MD 21620
      3 Beds4 Baths2,492 SqFt
      1/39 39
      Pending

      $745,000

      110 S MILL ST, Chestertown, MD 21620

      MLS# MDKE2005558

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 116 HARLAN LOOP, Chestertown, MD 21620
      5 Beds4 Baths4,067 SqFt
      1/21 21
      Active

      $529,000

      116 HARLAN LOOP, Chestertown, MD 21620

      MLS# MDKE2005610

      Listed by Samson Properties

      Bright MLS (BMLS)
    • 103 ADELA WAY, Chestertown, MD 21620
      4 Beds4 Baths5,576 SqFt
      1/90 90
      Under Contract

      $595,000

      103 ADELA WAY, Chestertown, MD 21620

      MLS# MDKE2005594

      Listed by Douglas Realty LLC

      Bright MLS (BMLS)
    • 7729 COUNTRY CLUB LN, Chestertown, MD 21620
      3 Beds3 Baths2,280 SqFt
      1/18 18
      Under Contract

      $635,000

      7729 COUNTRY CLUB LN, Chestertown, MD 21620

      MLS# MDKE2005552

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 907 N MEADOWVIEW DR, Chestertown, MD 21620
      3 Beds3 Baths1,842 SqFt
      1/33 33
      Price Dropped by $30K

      $410,000

      907 N MEADOWVIEW DR, Chestertown, MD 21620

      MLS# MDKE2005540

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 5700 JOHNSONTOWN RD, Chestertown, MD 21620
      3 Beds1 Bath1,144 SqFt
      1/7 7
      Price Dropped by $15K

      $110,000

      5700 JOHNSONTOWN RD, Chestertown, MD 21620

      MLS# MDKE2005562

      Listed by Tesla Realty Group, LLC

      Bright MLS (BMLS)
    • 108 S KENT ST, Chestertown, MD 21620
      1 Bed2 Baths936 SqFt
      1/19 19
      Active

      $315,000

      108 S KENT ST, Chestertown, MD 21620

      MLS# MDKE2005496

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 201 BOUNDARY AVE, Chestertown, MD 21620
      3 Beds3 Baths3,096 SqFt
      1/46 46
      Under Contract

      $449,000

      201 BOUNDARY AVE, Chestertown, MD 21620

      MLS# MDQA2014272

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 112 METCALF RD, Chestertown, MD 21620
      3 Beds2 Baths1,280 SqFt
      1/20 20
      Price Dropped by $10K

      $255,000

      112 METCALF RD, Chestertown, MD 21620

      MLS# MDKE2005498

      Listed by Engel & Volkers Annapolis

      Bright MLS (BMLS)
    • 251 DEVON DR, Chestertown, MD 21620
      3 Beds3 Baths3,935 SqFt
      1/54 54
      Active

      $595,000

      251 DEVON DR, Chestertown, MD 21620

      MLS# MDKE2005536

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 234 N COLLEGE AVE, Chestertown, MD 21620
      2 Beds1 Bath1,296 SqFt
      1/3 3
      Under Contract

      $164,000

      234 N COLLEGE AVE, Chestertown, MD 21620

      MLS# MDKE2005434

      Listed by Cummings & Co Realtors

      Bright MLS (BMLS)
    • 141 PROSPECT ST, Chestertown, MD 21620
      4 Beds2 Baths1,156 SqFt
      1/16 16
      Active

      $167,000

      141 PROSPECT ST, Chestertown, MD 21620

      MLS# MDKE2005504

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 132 PROSPECT ST, Chestertown, MD 21620
      2 Beds1 Bath910 SqFt
      1/10 10
      Active

      $62,400

      132 PROSPECT ST, Chestertown, MD 21620

      MLS# MDKE2005444

      Listed by ANR Realty, LLC

      Bright MLS (BMLS)
    • 165 CHAR NOR MANOR BLVD, Chestertown, MD 21620
      4 Beds3 Baths2,258 SqFt
      1/67 67
      Price Dropped by $25K

      $450,000

      165 CHAR NOR MANOR BLVD, Chestertown, MD 21620

      MLS# MDQA2013956

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 26933 MALLARD RD, Chestertown, MD 21620
      3 Beds3 Baths1,600 SqFt
      1/15 15
      Under Contract

      $625,000

      26933 MALLARD RD, Chestertown, MD 21620

      MLS# MDKE2005422

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 134 CHAR NOR MANOR BLVD, Chestertown, MD 21620
      3 Beds1 Bath1,128 SqFt
      1/42 42
      Price Dropped by $34K

      $285,000

      134 CHAR NOR MANOR BLVD, Chestertown, MD 21620

      MLS# MDQA2013988

      Listed by Meredith Fine Properties

      Bright MLS (BMLS)
    • 201 BIRCH RUN RD, Chestertown, MD 21620
      3 Beds2 Baths1,588 SqFt
      1/23 23
      Active

      $470,000

      201 BIRCH RUN RD, Chestertown, MD 21620

      MLS# MDKE2005380

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 300 HICKORY LN, Chestertown, MD 21620
      5 Beds4 Baths3,640 SqFt
      1/30 30
      Active

      $1,198,000

      300 HICKORY LN, Chestertown, MD 21620

      MLS# MDQA2013388

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 23069 RALEIGH RD, Chestertown, MD 21620
      2 Beds2 Baths1,160 SqFt
      1/10 10
      Pending

      $175,000

      23069 RALEIGH RD, Chestertown, MD 21620

      MLS# MDKE2005378

      Listed by Keller Williams Select Realtors of Annapolis

      Bright MLS (BMLS)
    • 624 HIGH ST, Chestertown, MD 21620
      2 Beds1 Bath1,290 SqFt
      1/3 3
      Active

      $240,000

      624 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005274

      Listed by Tesla Realty Group, LLC

      Bright MLS (BMLS)
    • 7961 QUAKER NECK RD, Chestertown, MD 21620
      5 Beds4 Baths4,167 SqFt
      1/93 93
      Pending

      $1,550,000

      7961 QUAKER NECK RD, Chestertown, MD 21620

      MLS# MDKE2005090

      Listed by Compass

      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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        About
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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