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    City: Chestertown, MD
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    18 Properties Available In Chestertown

    18 Properties Available In Chestertown

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    MD >Chestertown >
    Market Insights
    103 TRAFFORD DR, Chestertown, MD 21620
    1/65
    Open Sat 11AM-1PM

    $399,900

    3 Beds3 Baths1,944 SqFt

    103 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    234 N COLLEGE AVE, Chestertown, MD 21620
    1/3
    Price Dropped by $20K

    $100,000

    2 Beds1 Bath1,296 SqFt

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
    110 PROSPECT ST, Chestertown, MD 21620
    1/6
    Active

    $119,895

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    Price Dropped by $25K

    $425,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    240 MERGANSER DR, Chestertown, MD 21620
    1/51
    Price Dropped by $10K
    3D

    $389,000

    3 Beds2 Baths1,120 SqFt

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    107 FLYING CLOUD DR, Chestertown, MD 21620
    1/51
    Price Dropped by $10K

    $385,000

    5 Beds4 Baths2,534 SqFt

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510

    Listed by CENTURY 21 New Millennium

    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)
    214 SILVER HEEL RD, Chestertown, MD 21620
    1/26
    Price Dropped by $10K

    $340,000

    4 Beds3 Baths1,972 SqFt

    214 SILVER HEEL RD, Chestertown, MD 21620

    MLS# MDKE2006498

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    144 PROSPECT ST, Chestertown, MD 21620
    1/18
    Under Contract

    $159,000

    2 Beds2 Baths1,082 SqFt

    144 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006494

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    21217 TEXAS AVE, Chestertown, MD 21620
    1/20
    Price Dropped by $20K

    $244,500

    2 Beds1 Bath912 SqFt

    21217 TEXAS AVE, Chestertown, MD 21620

    MLS# MDKE2006364

    Listed by RE/MAX Leading Edge

    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)
    222 MOUNT VERNON AVE, Chestertown, MD 21620
    1/29
    Price Dropped by $5K

    $429,999

    4 Beds2 Baths1,656 SqFt

    222 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2005876

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    8886 GEORGETOWN RD, Chestertown, MD 21620
    1/3
    Price Dropped by $5K

    $80,000

    4.03 Acres

    8886 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2006634

    Listed by Samson Properties

    Bright MLS (BMLS)
    1010 TWIN CT, Chestertown, MD 21620
    1/14
    Active

    $2,400

    4 Beds2 Baths1,476 SqFt

    1010 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006610

    Listed by Kevin Dey Realty

    Bright MLS (BMLS)
    228 MERGANSER DR, Chestertown, MD 21620
    1/13
    Price Dropped by $24K

    $75,000

    0.51 Acres

    228 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2017240

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    7501 CHURCH HILL RD #5, Chestertown, MD 21620
    1/17
    Active

    $1,800

    2 Beds1 Bath1,000 SqFt

    7501 CHURCH HILL RD #5, Chestertown, MD 21620

    MLS# MDQA2016372

    Listed by Brenton Realty Group

    Bright MLS (BMLS)
    201 N LYNCHBURG ST, Chestertown, MD 21620
    1/13
    Price Dropped by $45K

    $750,000

    4,342 Sqft Lot

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006082

    Listed by RE/MAX Associates-Hockessin

    Bright MLS (BMLS)
    JOHNSONTOWN RD, Chestertown, MD 21620
    1/16
    Price Dropped by $10K

    $25,000

    0.9 Acres

    JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005550

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
    • 1

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    AMB (1)
    AMB Property Group | Keller Williams Capital Properties
    Angelica Dennis
        Top Areas
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    +1(240) 688-8762
    angelica@ambpropertygroup.com
    519 C Street NE, Washington, DC, 20002

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    AMB (1)
    AMB Property Group | Keller Williams Capital Properties
    Angelica Dennis
        Top Areas
        1. Prince Georges County
        2. Montgomery County
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        5. Charles County
        6. Washington, DC
        7. Northern Virginia
        Buyers
        1. Mortgage Calculator
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        1. Home Valuation
        2. Sell My Home
        3. Services
        4. Schedule
        Market Snapshot
        News
        About Us
    +1(240) 688-8762
    angelica@ambpropertygroup.com
    519 C Street NE, Washington, DC, 20002

    Get My App

    Do Not Sell or Share My Personal Data
    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.

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

    Powered by Lofty Inc. Copyright 2026. All Rights Reserved.