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    134 Properties
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    134 Properties Available

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    • Newest Listings
    • Beds (Most)
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    • 101 S MILL ST, Chestertown, MD 21620
      2 Beds3 Baths1,476 SqFt
      1/22 22
      Under Contract

      $485,000

      101 S MILL ST, Chestertown, MD 21620

      MLS# MDKE2004984

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 7483 SHORTALL ST, Chestertown, MD 21620
      3 Beds2 Baths1,232 SqFt
      1/37 37
      Pending

      $285,000

      7483 SHORTALL ST, Chestertown, MD 21620

      MLS# MDKE2004948

      Listed by RE/MAX Executive

      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
      Price Dropped by $10K

      $289,900

      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

      $235,000

      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
      Open Sun 11AM-1PM

      $1,395,500

      105 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2005002

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • COGAR RD, Chestertown, MD 21620
      0.34 Acres
      1/2 2
      Price Dropped by $10K

      $25,000

      COGAR RD, Chestertown, MD 21620

      MLS# MDKE2004996

      Listed by Compass

      Bright MLS (BMLS)
    • TONOPAH RD, Chestertown, MD 21620
      0.34 Acres
      1/2 2
      Price Dropped by $10K

      $25,000

      TONOPAH RD, Chestertown, MD 21620

      MLS# MDKE2004994

      Listed by Compass

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

      $579,000

      103 LANDING LN, Chestertown, MD 21620

      MLS# MDKE2004972

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 110 PHILOSOPHERS TER, Chestertown, MD 21620
      2 Beds1 Bath896 SqFt
      1/22 22
      Price Dropped by $25K

      $199,900

      110 PHILOSOPHERS TER, Chestertown, MD 21620

      MLS# MDKE2004982

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • OLD MORGNEC RD, Chestertown, MD 21620
      1.37 Acres
      Active

      $64,000

      OLD MORGNEC RD, Chestertown, MD 21620

      MLS# MDKE2004974

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • 128 EDMORE RD, Chestertown, MD 21620
      4 Beds2 Baths2,568 SqFt
      1/57 57
      Price Dropped by $15K

      $425,000

      128 EDMORE RD, Chestertown, MD 21620

      MLS# MDQA2012546

      Listed by Berkshire Hathaway HomeServices PenFed Realty

      Bright MLS (BMLS)
    • 306 CEDAR ST, Chestertown, MD 21620
      4 Beds2 Baths1,404 SqFt
      1/42 42
      Under Contract

      $319,000

      306 CEDAR ST, Chestertown, MD 21620

      MLS# MDKE2004954

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 128 N QUEEN ST, Chestertown, MD 21620
      2 Beds1 Bath1,455 SqFt
      1/19 19
      Under Contract

      $1,900

      128 N QUEEN ST, Chestertown, MD 21620

      MLS# MDKE2004958

      Listed by Brenton Realty Group

      Bright MLS (BMLS)
    • CLOQUET RD, Chestertown, MD 21620
      1.51 Acres
      1/11 11
      Active

      $49,900

      CLOQUET RD, Chestertown, MD 21620

      MLS# MDKE2004960

      Listed by Berkshire Hathaway HomeServices Homesale Realty

      Bright MLS (BMLS)
    • 314 DEVON DR, Chestertown, MD 21620
      4 Beds4 Baths3,420 SqFt
      1/47 47
      Active

      $514,500

      314 DEVON DR, Chestertown, MD 21620

      MLS# MDKE2004946

      Listed by The Parker Group

      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)
    • 118 TUXEDO RD, Chestertown, MD 21620
      3 Beds1 Bath1,056 SqFt
      1/26 26
      Active

      $274,000

      118 TUXEDO RD, Chestertown, MD 21620

      MLS# MDQA2012402

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 21217 TEXAS AVE, Chestertown, MD 21620
      2 Beds1 Bath912 SqFt
      1/16 16
      Price Dropped by $17K

      $249,900

      21217 TEXAS AVE, Chestertown, MD 21620

      MLS# MDKE2004902

      Listed by RE/MAX Leading Edge

      Bright MLS (BMLS)
    • 109 TAMARACK RD, Chestertown, MD 21620
      3 Beds2 Baths1,560 SqFt
      1/53 53
      Under Contract

      $324,900

      109 TAMARACK RD, Chestertown, MD 21620

      MLS# MDQA2012102

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 24576 LANGFORD RD, Chestertown, MD 21620
      3 Beds3 Baths4,023 SqFt
      1/94 94
      Price Dropped by $40K

      $845,000

      24576 LANGFORD RD, Chestertown, MD 21620

      MLS# MDKE2004906

      Listed by Maryland Heritage Properties

      Bright MLS (BMLS)
    • 10578 TONOPAH RD, Chestertown, MD 21620
      3 Beds3 Baths0.35 Acres Lot
      1/19 19
      Under Contract

      $329,900

      10578 TONOPAH RD, Chestertown, MD 21620

      MLS# MDKE2004894

      Listed by RE/MAX Executive

      Bright MLS (BMLS)
    • 110 FLYING CLOUD COURT, Chestertown, MD 21620
      3 Beds3 Baths1,856 SqFt
      1/17 17
      Active

      $349,900

      110 FLYING CLOUD COURT, Chestertown, MD 21620

      MLS# MDKE2004850

      Listed by Berkshire Hathaway HomeServices Homesale Realty

      Bright MLS (BMLS)
    • TOWHEE RD, Chestertown, MD 21620
      0.34 Acres
      1/4 4
      Pending

      $5,000

      TOWHEE RD, Chestertown, MD 21620

      MLS# MDKE2004882

      Listed by Ashland Auction Group 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.
    IMG_20231010_020750 (1)
    R.I.C. Home Team @ Bennett Realty Solutions
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    6301 Ivy Lane #805, Greenbelt, Maryland 20770

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    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.
    IMG_20231010_020750 (1)
    R.I.C. Home Team @ Bennett Realty Solutions
    Reliable Investment Consulting
    +1(301) 823-5800
    support@richometeam.com
    6301 Ivy Lane #805, Greenbelt, Maryland 20770

    Get My App

      • Home
        Property Management
        1. Request a Consultation
        2. Rental Application
        3. Resident Login
        4. Owner & Manager Login
        5. Available Properties for Rent
        Market Snapshot
      • Buy
        1. Mortgage Calculator
        2. Affordability Calculator
        3. Featured Listings
        4. All Listings
        5. Sold Listings
        About
        1. About Us
        2. Meet the Team
        3. Contact Us
        4. Reviews
        Blogs
      • Sell
        1. Sell My Home
        2. Home Valuation
        Popular Areas
        1. Alexandria Overview
        2. Arlington Overview
        3. Washington Overview
        4. Baltimore Overview
        5. Silver Spring Overview
        6. Upper Marlboro Overview
        7. Hyattsville Overview
        8. Waldorf Overview

    Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

    Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility