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    139 Properties
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    139 Properties Available

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    The average price in the selected areas has remained stable. Learn more
    • 907 N MEADOWVIEW DR, Chestertown, MD 21620
      3 Beds3 Baths1,842 SqFt
      1/33 33
      Open 8/23 11AM-1PM

      $440,000

      907 N MEADOWVIEW DR, Chestertown, MD 21620

      MLS# MDKE2005540

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 101 BIRCH RUN RD, Chestertown, MD 21620
      3 Beds2 Baths1,961 SqFt
      1/22 22
      Open 8/23 11AM-1PM

      $549,000

      101 BIRCH RUN RD, Chestertown, MD 21620

      MLS# MDKE2005088

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 103 LANDING LN, Chestertown, MD 21620
      2 Beds3 Baths2,100 SqFt
      1/41 41
      Open 8/23 11AM-1PM

      $569,000

      103 LANDING LN, Chestertown, MD 21620

      MLS# MDKE2004972

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 349 HIGH ST, Chestertown, MD 21620
      7 Beds4 Baths3,664 SqFt
      1/33 33
      Open 8/31 12PM-2PM

      $395,000

      349 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2004076

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 224 VALLEY RD, Chestertown, MD 21620
      3 Beds2 Baths1,886 SqFt
      1/24 24
      New

      $450,000

      224 VALLEY RD, Chestertown, MD 21620

      MLS# MDKE2005546

      Listed by Cross Street Realtors LLC

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

      $538,000

      116 HARLAN LOOP, Chestertown, MD 21620

      MLS# MDKE2005610

      Listed by Samson Properties

      Bright MLS (BMLS)
    • 200 WASHINGTON AVE, Chestertown, MD 21620
      4 Beds4 Baths2,917 SqFt
      1/35 35
      New

      $795,000

      200 WASHINGTON AVE, Chestertown, MD 21620

      MLS# MDKE2005538

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 200 FEY RD, Chestertown, MD 21620
      3 Beds2 Baths1,572 SqFt
      1/18 18
      New

      $374,900

      200 FEY RD, Chestertown, MD 21620

      MLS# MDQA2014600

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • 8978 ORCHARD DR, Chestertown, MD 21620
      4 Beds3 Baths3,820 SqFt
      1/44 44
      Coming Soon

      $675,000

      8978 ORCHARD DR, Chestertown, MD 21620

      MLS# MDKE2005500

      Listed by TTR Sotheby's International Realty

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

      $615,000

      103 ADELA WAY, Chestertown, MD 21620

      MLS# MDKE2005594

      Listed by Douglas Realty LLC

      Bright MLS (BMLS)
    • 492 PEAR TREE POINT RD, Chestertown, MD 21620
      3 Beds2 Baths2,600 SqFt
      1/42 42
      New

      $1,100,000

      492 PEAR TREE POINT RD, Chestertown, MD 21620

      MLS# MDQA2013108

      Listed by Meredith Fine Properties

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

      $635,000

      7729 COUNTRY CLUB LN, Chestertown, MD 21620

      MLS# MDKE2005552

      Listed by Cross Street Realtors LLC

      Bright MLS (BMLS)
    • 10165 JOHN CARVILL RD, Chestertown, MD 21620
      3 Beds3 Baths2,774 SqFt
      1/20 20
      Active

      $549,000

      10165 JOHN CARVILL RD, Chestertown, MD 21620

      MLS# MDKE2005476

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 5700 JOHNSONTOWN RD, Chestertown, MD 21620
      3 Beds1 Bath1,144 SqFt
      1/7 7
      Active

      $125,000

      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

      $325,000

      108 S KENT ST, Chestertown, MD 21620

      MLS# MDKE2005496

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 143 CHAR NOR MANOR BLVD, Chestertown, MD 21620
      3 Beds3 Baths2,073 SqFt
      3D
      Under Contract

      $868,000

      143 CHAR NOR MANOR BLVD, Chestertown, MD 21620

      MLS# MDQA2014274

      Listed by Redfin Corp

      Bright MLS (BMLS)
    • 201 BOUNDARY AVE, Chestertown, MD 21620
      4 Beds3 Baths3,096 SqFt
      1/49 49
      Under Contract

      $470,000

      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 $15K

      $265,000

      112 METCALF RD, Chestertown, MD 21620

      MLS# MDKE2005498

      Listed by Engel & Volkers Annapolis

      Bright MLS (BMLS)
    • 600 ROSIN DR, Chestertown, MD 21620
      3 Beds3 Baths1,300 SqFt
      1/36 36
      Active

      $424,000

      600 ROSIN DR, Chestertown, MD 21620

      MLS# MDQA2014374

      Listed by Cross Street Realtors LLC

      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
      Price Dropped by $15K

      $184,900

      234 N COLLEGE AVE, Chestertown, MD 21620

      MLS# MDKE2005434

      Listed by Cummings & Co Realtors

      Bright MLS (BMLS)
    • 9194 N BAYVIEW AVE, Chestertown, MD 21620
      2 Beds2 Baths1,460 SqFt
      1/45 45
      Under Contract

      $698,000

      9194 N BAYVIEW AVE, Chestertown, MD 21620

      MLS# MDKE2005488

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 9190 N BAYVIEW AVE, Chestertown, MD 21620
      2 Beds1 Bath1,160 SqFt
      1/38 38
      Under Contract

      $319,500

      9190 N BAYVIEW AVE, Chestertown, MD 21620

      MLS# MDKE2005442

      Listed by Select Land & Homes, LLC

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

      $175,000

      141 PROSPECT ST, Chestertown, MD 21620

      MLS# MDKE2005504

      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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        About
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    Logo - Broker9584573-2025_Plaque_AwardProud Partner of FGP

    Samson Properties

    Jess Santizo Lic# 0225264890

    +1(240) 381-4804 info@jessicarealtor.com

    3919 National Dr Suite 310, Burtonsville, MD, 20866, 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. Recent Listings
        Communities
        1. Washington
        2. Baltimore City
        3. Baltimore
        4. Montgomery
        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
    Logo - Broker9584573-2025_Plaque_AwardProud Partner of FGP

    Samson Properties

    Jess Santizo Lic# 0225264890

    +1(240) 381-4804 info@jessicarealtor.com

    3919 National Dr Suite 310, Burtonsville, MD, 20866, 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