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    ZIP Code: 21620
    Price Reduced
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    22 Properties Available

    22 Properties Available

    • Newest Listings
    • Price-High To Low
    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    8820 CUMBERLAND ST, Chestertown, MD 21620
    1/24
    Price Dropped by $31K
    3D

    $281,500

    3 Beds2 Baths1,080 SqFt

    8820 CUMBERLAND ST, Chestertown, MD 21620

    MLS# MDKE2007156

    Listed by RE/MAX Advantage Realty

    Bright MLS (BMLS)
    329 UNION CHURCH RD, Chestertown, MD 21620
    1/142
    Price Dropped by $19K

    $549,900

    4 Beds3 Baths2,464 SqFt

    329 UNION CHURCH RD, Chestertown, MD 21620

    MLS# MDQA2018610

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    22974 BAY SHORE RD, Chestertown, MD 21620
    1/22
    Price Dropped by $14K
    3D

    $315,000

    2 Beds2 Baths1,440 SqFt

    22974 BAY SHORE RD, Chestertown, MD 21620

    MLS# MDKE2007106

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    24775 LANGFORD RD, Chestertown, MD 21620
    1/25
    Price Dropped by $10K

    $305,000

    3 Beds1 Bath1,008 SqFt

    24775 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2007012

    Listed by RE/MAX Chesapeake

    Bright MLS (BMLS)
    104 LINCOLN DR, Chestertown, MD 21620
    1/30
    Price Dropped by $10K

    $275,000

    3 Beds1 Bath960 SqFt

    104 LINCOLN DR, Chestertown, MD 21620

    MLS# MDKE2007032

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    TOWHEE RD, Chestertown, MD 21620
    1/2
    Price Dropped by $10K

    $40,000

    0.55 Acres

    TOWHEE RD, Chestertown, MD 21620

    MLS# MDKE2007066

    Listed by The Parker Group

    Bright MLS (BMLS)
    115 CHESTER ARMS DR, Chestertown, MD 21620
    1/34
    Price Dropped by $4K

    $259,000

    3 Beds2 Baths1,140 SqFt

    115 CHESTER ARMS DR, Chestertown, MD 21620

    MLS# MDKE2006958

    Listed by Samson Properties

    Bright MLS (BMLS)
    7415 WILKINS LN, Chestertown, MD 21620
    1/23
    Price Dropped by $7K

    $222,000

    3 Beds1 Bath936 SqFt

    7415 WILKINS LN, Chestertown, MD 21620

    MLS# MDKE2007030

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    216 BIRCH RUN RD, Chestertown, MD 21620
    1/52
    Price Dropped by $20K

    $730,000

    3 Beds3 Baths2,176 SqFt

    216 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2006896

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    10540 TONOPAH RD, Chestertown, MD 21620
    1/21
    Price Dropped by $2K

    $267,000

    3 Beds2 Baths1,404 SqFt

    10540 TONOPAH RD, Chestertown, MD 21620

    MLS# MDKE2006880

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    CANNON ST, Chestertown, MD 21620
    1/9
    Price Dropped by $154K

    $196,000

    0.22 Acres

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006940

    Listed by Taylor Properties

    Bright MLS (BMLS)
    CANNON ST, Chestertown, MD 21620
    1/9
    Price Dropped by $169K

    $281,000

    0.29 Acres

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006944

    Listed by Taylor Properties

    Bright MLS (BMLS)
    620 CANNON ST, Chestertown, MD 21620
    1/9
    Price Dropped by $14K

    $85,000

    0.07 Acres

    620 CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006922

    Listed by Taylor Properties

    Bright MLS (BMLS)
    305 ROOSEVELT DR, Chestertown, MD 21620
    1/2
    Price Dropped by $15K

    $45,000

    0.61 Acres

    305 ROOSEVELT DR, Chestertown, MD 21620

    MLS# MDKE2006830

    Listed by Taylor Properties

    Bright MLS (BMLS)
    234 N COLLEGE AVE, Chestertown, MD 21620
    1/3
    Price Dropped by $6K

    $79,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    10781 FERMOY RD, Chestertown, MD 21620
    1/54
    Active

    $429,500

    4 Beds3 Baths2,160 SqFt

    10781 FERMOY RD, Chestertown, MD 21620

    MLS# MDKE2006640

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    109 2ND ST, Chestertown, MD 21620
    Price Dropped by $10K

    $125,000

    1.8 Acres

    109 2ND ST, Chestertown, MD 21620

    MLS# MDQA2017232

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    106 QUEEN ST S, Chestertown, MD 21620
    1/92
    Price Dropped by $29K

    $799,900

    3 Beds4 Baths2,472 SqFt

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    23710 L RD, Chestertown, MD 21620
    1/2
    Price Dropped by $12K

    $12,000

    0.5 Acres

    23710 L RD, Chestertown, MD 21620

    MLS# MDKE2002838

    Listed by Paul Wesley Real Estate

    Bright MLS (BMLS)
    FISH HATCHERY RD, Chestertown, MD 21620
    1/2
    Price Dropped by $18K

    $18,500

    0.34 Acres

    FISH HATCHERY RD, Chestertown, MD 21620

    MLS# MDKE2002848

    Listed by Paul Wesley Real Estate

    Bright MLS (BMLS)
    REDFIELD RD, Chestertown, MD 21620
    1/2
    Price Dropped by $19K

    $19,000

    0.34 Acres

    REDFIELD RD, Chestertown, MD 21620

    MLS# MDKE2002842

    Listed by Paul Wesley Real Estate

    Bright MLS (BMLS)
    SPINNAKER RD, Chestertown, MD 21620
    1/2
    Price Dropped by $19K

    $19,000

    0.56 Acres

    SPINNAKER RD, Chestertown, MD 21620

    MLS# MDKE2002844

    Listed by Paul Wesley Real Estate

    Bright MLS (BMLS)
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    • Home
    • Featured Areas
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    • Meet the Team
      1. Meet The Ireland Group
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      3. Reviews
    • Buy
      1. All Listings
      2. Advanced Search
      3. Coming SOON!
      4. Price Reduced
      5. New Construction
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      8. Open Houses
      9. Buyer Guide
      10. Get Financing
    • Market Reports
      1. Annapolis Market Report
      2. Baltimore Market Report
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      4. Bowie Market Report
      5. Brandywine Market Report
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      7. College Park Market Report
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      11. Laurel Market Report
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      14. Randallstown Market Report
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      17. Waldorf Market Report
    • Blogs
    • Sell
      1. Home Valuation
      2. Sell My Home
      3. Seller Guide
      4. Recently Sold
    • Resources
      1. Montgomery County Council
      2. Ann Arundel County Council
      3. Howard County Council
      4. Things to Consider when Selling a Home
      5. Things to Consider when Buying a Home
      6. The Home Selling Process
      7. The Home Buying Process
    The Ireland Group | EXP Realty, LLC
    Gregory & Stephanie Ireland
    License ID: 632137

    +1(202) 550-0018 gregory@theirelandgroup.net

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    eXp Realty - WhiteTIG Logo white
    • Home
    • Featured Areas
      1. Washington, DC
      2. Maryland
    • Meet the Team
      1. Meet The Ireland Group
      2. Contact Us
      3. Reviews
    • Buy
      1. All Listings
      2. Advanced Search
      3. Coming SOON!
      4. Price Reduced
      5. New Construction
      6. 55 + Community
      7. Foreclosures
      8. Open Houses
      9. Buyer Guide
      10. Get Financing
    • Market Reports
      1. Annapolis Market Report
      2. Baltimore Market Report
      3. Baltimore City Market Report
      4. Bowie Market Report
      5. Brandywine Market Report
      6. Clinton Market Report
      7. College Park Market Report
      8. Columbia Market Report
      9. Crofton Market Report
      10. Edgewater Market Report
      11. Laurel Market Report
      12. Odenton Market Report
      13. Owings Mills Market Report
      14. Randallstown Market Report
      15. Towson Market Report
      16. Upper Marlboro Market Report
      17. Waldorf Market Report
    • Blogs
    • Sell
      1. Home Valuation
      2. Sell My Home
      3. Seller Guide
      4. Recently Sold
    • Resources
      1. Montgomery County Council
      2. Ann Arundel County Council
      3. Howard County Council
      4. Things to Consider when Selling a Home
      5. Things to Consider when Buying a Home
      6. The Home Selling Process
      7. The Home Buying Process
    The Ireland Group | EXP Realty, LLC
    Gregory & Stephanie Ireland
    License ID: 632137

    +1(202) 550-0018 gregory@theirelandgroup.net

    Get My App

    Powered by Lofty Inc. Copyright 2026. 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.