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    ZIP Code: 21620
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    24 Properties Available

    24 Properties Available

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    Address
    Price
    Beds
    Baths
    Area
    Status
    MLS

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005890 Listed by Coldwell Banker Chesapeake Real Estate Company

    $1,245,500

    5
    5
    3,243 SqFt
    Active
    MLS# MDKE2005890

    517 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2017680 Listed by Keller Williams Flagship

    $324,900

    3
    1
    1,248 SqFt
    Active
    MLS# MDQA2017680

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686 Listed by Cummings & Co. Realtors

    $239,900

    3
    2
    1,280 SqFt
    Active
    MLS# MDKE2006686

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670 Listed by Cummings & Co Realtors

    $100,000

    2
    1
    1,296 SqFt
    Active
    MLS# MDKE2006670

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626 Listed by ANR Realty, LLC

    $89,900

    3
    2
    2,210 SqFt
    Active
    MLS# MDKE2006626

    10781 FERMOY RD, Chestertown, MD 21620

    MLS# MDKE2006640 Listed by Real Broker, LLC - Chester

    $429,900

    4
    3
    2,160 SqFt
    Active
    MLS# MDKE2006640

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614 Listed by Benson & Mangold, LLC

    $399,900

    2
    3
    1,518 SqFt
    Active
    MLS# MDKE2006614

    102 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006586 Listed by Long & Foster Real Estate, Inc.

    $329,900

    3
    3
    1,896 SqFt
    Active
    MLS# MDKE2006586

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900 Listed by Chesapeake Real Estate Associates, LLC

    $365,000

    3
    2
    1,120 SqFt
    Active
    MLS# MDQA2016900

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510 Listed by CENTURY 21 New Millennium

    $375,000

    5
    4
    2,534 SqFt
    Active
    MLS# MDKE2006510

    214 SILVER HEEL RD, Chestertown, MD 21620

    MLS# MDKE2006498 Listed by Cross Street Realtors LLC

    $340,000

    4
    3
    1,972 SqFt
    Active
    MLS# MDKE2006498

    144 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006494 Listed by Doug Ashley Realtors, LLC

    $159,000

    2
    2
    1,082 SqFt
    Under Contract
    MLS# MDKE2006494

    101 COLEMAN DR, Chestertown, MD 21620

    MLS# MDQA2016624 Listed by Coldwell Banker Chesapeake Real Estate Company

    $519,900

    3
    3
    2,268 SqFt
    Active
    MLS# MDQA2016624

    139 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006250 Listed by Redfin Corp

    $198,000

    3
    1
    1,200 SqFt
    Under Contract
    MLS# MDKE2006250

    8276 BROAD NECK RD, Chestertown, MD 21620

    MLS# MDKE2006216 Listed by Coldwell Banker Chesapeake Real Estate Company

    $1,395,000

    4
    4
    3,383 SqFt
    Active
    MLS# MDKE2006216

    222 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2005876 Listed by Long & Foster Real Estate, Inc.

    $419,999

    4
    2
    1,656 SqFt
    Active
    MLS# MDKE2005876

    8886 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2006634 Listed by Samson Properties

    $80,000

    --
    --
    4.03 Acres
    Active
    MLS# MDKE2006634

    1010 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006610 Listed by Kevin Dey Realty

    $2,400

    4
    2
    1,476 SqFt
    Active
    MLS# MDKE2006610

    SANDY BOTTOM RD, Chestertown, MD 21620

    MLS# MDKE2006554 Listed by Village Real Estate Company LLC

    $59,000

    --
    --
    1.95 Acres
    Active
    MLS# MDKE2006554

    228 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2017240 Listed by Benson & Mangold, LLC

    $59,999

    --
    --
    0.51 Acres
    Active
    MLS# MDQA2017240

    104 MAPLE AVE, Chestertown, MD 21620

    MLS# MDKE2006386 Listed by Real Broker, LLC - Annapolis

    $1,350,000

    --
    --
    10,540 Sqft Lot
    Active
    MLS# MDKE2006386

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006082 Listed by RE/MAX Associates-Hockessin

    $750,000

    --
    --
    4,342 Sqft Lot
    Active
    MLS# MDKE2006082

    JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005550 Listed by Berkshire Hathaway HomeServices PenFed Realty

    $25,000

    --
    --
    0.9 Acres
    Active
    MLS# MDKE2005550

    515 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2000776 Listed by EShore

    $795,000

    --
    --
    0.97 Acres Lot
    Active
    MLS# MDKE2000776
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    Team Allen LLC_LOGO_A1
    Blue Crab Real Estate LLC

    David Allen

    +1(301) 524-7840 davidallen@bluecrabrealty.com

    304 E 16th St Frederick, MD 21701
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    Team Allen LLC_LOGO_A1
    Blue Crab Real Estate LLC

    David Allen

    +1(301) 524-7840 davidallen@bluecrabrealty.com

    304 E 16th St Frederick, MD 21701
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        Market Snapshot
      • Buy
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    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.