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    134 Properties
    Map

    134 Properties Available In 21620

    • Default
    • Price-High To Low
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    • Newest Listings
    • Beds (Most)
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    MD >21620 >
    Market Insights
    • TEXAS AVE, Chestertown, MD 21620
      0.09 Acres
      1/2 2
      Active

      $10,000

      TEXAS AVE, Chestertown, MD 21620

      MLS# MDKE2004610

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • 23393 CACAWAY FARM LN, Chestertown, MD 21620
      3 Beds4 Baths4,446 SqFt
      1/44 44
      Active

      $1,450,000

      23393 CACAWAY FARM LN, Chestertown, MD 21620

      MLS# MDKE2004002

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620
      16,977 SqFt
      1/30 30
      Active

      $425

      870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620

      MLS# MDKE2004432

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 116 PINE CHIP RD, Chestertown, MD 21620
      3 Beds2 Baths2,767 SqFt
      1/35 35
      Active

      $515,000

      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)
    • MONTGOMERY AVE, Chestertown, MD 21620
      0.11 Acres
      Price Dropped by $5K

      $10,000

      MONTGOMERY AVE, Chestertown, MD 21620

      MLS# MDKE2004196

      Listed by Chesapeake Real Estate Associates, LLC

      Bright MLS (BMLS)
    • 860 HIGH ST, Chestertown, MD 21620
      3,114 SqFt
      1/38 38
      Active

      $860,000

      860 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2004138

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 870 HIGH ST, Chestertown, MD 21620
      16,977 SqFt
      1/72 72
      Active

      $1,870,000

      870 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2004140

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 349 HIGH ST, Chestertown, MD 21620
      7 Beds4 Baths3,664 SqFt
      1/33 33
      Price Dropped by $30K

      $395,000

      349 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2004076

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • BUCK NECK LANDING RD, Chestertown, MD 21620
      0.34 Acres
      Active

      $9,500

      BUCK NECK LANDING RD, Chestertown, MD 21620

      MLS# MDKE2004072

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • MILLBROOK DR, Chestertown, MD 21620
      0.5 Acres
      Pending

      $12,500

      MILLBROOK DR, Chestertown, MD 21620

      MLS# MDKE2004060

      Listed by Long & Foster Real Estate, Inc.

      Bright MLS (BMLS)
    • LOT 9 PRESTWICK DR, Chestertown, MD 21620
      1.95 Acres
      1/20 20
      Active

      $212,000

      LOT 9 PRESTWICK DR, Chestertown, MD 21620

      MLS# MDKE2003918

      Listed by Gunther-McClary Real Estate

      Bright MLS (BMLS)
    • 860 & 870 HIGH ST, Chestertown, MD 21620
      16,977 SqFt
      1/92 92
      Price Dropped by $300K

      $2,400,000

      860 & 870 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2003850

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 349 & 351 HIGH ST, Chestertown, MD 21620
      3,664 SqFt
      1/47 47
      Price Dropped by $30K

      $395,000

      349 & 351 HIGH ST, Chestertown, MD 21620

      MLS# MDKE2003720

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • PARCEL BUCK NECK LDG RD, Chestertown, MD 21620
      0.34 Acres
      1/6 6
      Active

      $10,000

      PARCEL BUCK NECK LDG RD, Chestertown, MD 21620

      MLS# MDKE2003874

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • SANDPIPER RD, Chestertown, MD 21620
      0.34 Acres
      1/5 5
      Pending

      $10,000

      SANDPIPER RD, Chestertown, MD 21620

      MLS# MDKE2003870

      Listed by Ashland Auction Group LLC

      Bright MLS (BMLS)
    • 117 N WATER ST N #3B, Chestertown, MD 21620
      1 Bed1 Bath652 SqFt
      1/24 24
      Price Dropped by $48K

      $299,900

      117 N WATER ST N #3B, Chestertown, MD 21620

      MLS# MDKE2003722

      Listed by Gunther-McClary Real Estate

      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)
    • 870 HIGH ST #2-3, Chestertown, MD 21620
      16,977 SqFt
      1/55 55
      Active

      $18

      870 HIGH ST #2-3, Chestertown, MD 21620

      MLS# MDKE2003776

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 870 HIGH ST #2, Chestertown, MD 21620
      16,977 SqFt
      1/35 35
      Active

      $18

      870 HIGH ST #2, Chestertown, MD 21620

      MLS# MDKE2003772

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • 870 HIGH ST #3, Chestertown, MD 21620
      16,977 SqFt
      1/36 36
      Active

      $18

      870 HIGH ST #3, Chestertown, MD 21620

      MLS# MDKE2003766

      Listed by Taylor Properties

      Bright MLS (BMLS)
    • ELM RD, Chestertown, MD 21620
      0.09 Acres
      1/3 3
      Active

      $20,000

      ELM RD, Chestertown, MD 21620

      MLS# MDKE2003590

      Listed by Coldwell Banker Chesapeake Real Estate Company

      Bright MLS (BMLS)
    • MAP 36 PARCEL 80 WATERTOWER RD, Chestertown, MD 21620
      0.7 Acres
      1/3 3
      Active

      $55,000

      MAP 36 PARCEL 80 WATERTOWER RD, Chestertown, MD 21620

      MLS# MDKE2003624

      Listed by Doug Ashley Realtors, LLC

      Bright MLS (BMLS)
    • 206 CANNON ST, Chestertown, MD 21620
      1.56 Acres
      1/9 9
      Price Dropped by $100K

      $1,150,000

      206 CANNON ST, Chestertown, MD 21620

      MLS# MDKE2003620

      Listed by Benson & Mangold, LLC

      Bright MLS (BMLS)
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    explore listings in 21620

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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
    Reliable Investment Consulting
    +1(301) 823-5800
    support@richometeam.com
    6301 Ivy Lane #805, Greenbelt, Maryland 20770

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      • Sell
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        Popular Areas
        1. Alexandria Overview
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        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

    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