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    • List
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    ZIP Code: 21620
    Virtual Tour
    Map
    23 Properties Available In 21620

    23 Properties Available In 21620

    • Newest Listings
    • Price-High To Low
    • Price-Low To High
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    MD >21620 >
    Market Insights
    23264 CLARISSA RD, Chestertown, MD 21620
    1/30
    New

    $365,000

    3 Beds2 Baths1,248 SqFt

    23264 CLARISSA RD, Chestertown, MD 21620

    MLS# MDKE2006096

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    8796 MARYLAND PKWY, Chestertown, MD 21620
    1/60
    New

    $1,650,000

    9 Beds7 Baths4,776 SqFt

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    213 BYFORD DR, Chestertown, MD 21620
    1/39
    New

    $380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    25440 LEARMAN RD, Chestertown, MD 21620
    1/70
    Active

    $3,000,000

    3 Beds4 Baths3,142 SqFt

    25440 LEARMAN RD, Chestertown, MD 21620

    MLS# MDKE2006468

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    956 WASHINGTON AVE, Chestertown, MD 21620
    1/29
    Active

    $285,000

    3 Beds1 Bath1,248 SqFt

    956 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006394

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    240 MERGANSER DR, Chestertown, MD 21620
    1/51
    Price Dropped by $26K
    3D

    $399,000

    3 Beds2 Baths1,120 SqFt

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    304 HADAWAY DR, Chestertown, MD 21620
    1/38
    Price Dropped by $7K
    3D

    $314,900

    4 Beds2 Baths1,325 SqFt

    304 HADAWAY DR, Chestertown, MD 21620

    MLS# MDKE2006482

    Listed by Redfin Corporation

    Bright MLS (BMLS)
    103 SUTTON WAY, Chestertown, MD 21620
    1/53
    Active

    $550,000

    5 Beds4 Baths3,816 SqFt

    103 SUTTON WAY, Chestertown, MD 21620

    MLS# MDKE2006344

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    109 WILTON RD, Chestertown, MD 21620
    1/31
    Active

    $344,900

    3 Beds2 Baths1,392 SqFt

    109 WILTON RD, Chestertown, MD 21620

    MLS# MDQA2016312

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    117 WATER ST N #1A, Chestertown, MD 21620
    1/46
    Active

    $685,000

    3 Beds3 Baths3,000 SqFt

    117 WATER ST N #1A, Chestertown, MD 21620

    MLS# MDKE2006162

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
    1/73
    Active

    $1,600,000

    7 Beds5 Baths5,400 SqFt

    117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

    MLS# MDKE2006158

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #1B, Chestertown, MD 21620
    1/20
    Active

    $200,000

    1 Bed1 Bath700 SqFt

    117 WATER ST N #1B, Chestertown, MD 21620

    MLS# MDKE2006164

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #2A, Chestertown, MD 21620
    1/24
    Active

    $375,000

    2 Beds1 Bath787 SqFt

    117 WATER ST N #2A, Chestertown, MD 21620

    MLS# MDKE2006166

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #2B, Chestertown, MD 21620
    1/23
    Active

    $350,000

    1 Bed1 Bath850 SqFt

    117 WATER ST N #2B, Chestertown, MD 21620

    MLS# MDKE2006168

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    204 DOUBLE CREEK RD, Chestertown, MD 21620
    1/46
    Price Dropped by $33K

    $565,000

    3 Beds3 Baths2,927 SqFt

    204 DOUBLE CREEK RD, Chestertown, MD 21620

    MLS# MDQA2015996

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    110 TRAFFORD DR, Chestertown, MD 21620
    1/22
    Price Dropped by $15K

    $450,000

    4 Beds3 Baths2,880 SqFt

    110 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2005964

    Listed by RE/MAX Advantage Realty

    Bright MLS (BMLS)
    218 CAMELOT DR, Chestertown, MD 21620
    1/45
    Price Dropped by $10K

    $499,999

    5 Beds4 Baths3,932 SqFt

    218 CAMELOT DR, Chestertown, MD 21620

    MLS# MDKE2005982

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
    311 DEVON DR, Chestertown, MD 21620
    1/41
    Price Dropped by $24K

    $475,000

    4 Beds3 Baths3,504 SqFt

    311 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2005930

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    LITTLE HARBOR WAY #1, Chestertown, MD 21620
    1/25
    Active

    $1,459,000

    3 Beds3 Baths2,231 SqFt

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2005768

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    105 HIGH ST, Chestertown, MD 21620
    1/48
    Price Dropped by $100K

    $1,295,500

    5 Beds5 Baths3,243 SqFt

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005890

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    8620 PARK DR, Chestertown, MD 21620
    1/66
    Active

    $499,900

    4 Beds3 Baths2,524 SqFt

    8620 PARK DR, Chestertown, MD 21620

    MLS# MDKE2005850

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    7989 QUAKER NECK RD, Chestertown, MD 21620
    1/90
    Open Sat 11AM-1PM
    3D

    $2,200,000

    5 Beds5 Baths4,305 SqFt

    7989 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    LITTLE HARBOR WAY #1, Chestertown, MD 21620
    1/29
    Active

    $1,800,000

    4 Beds4 Baths3,540 SqFt

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2004992

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    • 1

    explore listings in 21620

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      • 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

    +1(833) 335-7433 homes@theirelandgroup.com

    Get My App

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    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.
    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

    +1(833) 335-7433 homes@theirelandgroup.com

    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.