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    Neighborhood: Chestertown, Chestertown, MD
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    10 Properties Available In Chestertown

    10 Properties Available In Chestertown

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    MD >Chestertown >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
    New

    $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)
    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)
    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)
    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)
    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)
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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
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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.

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    Bayside Logo . PNG

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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
        2. Denton Overview
        3. Trappe Overview
        4. Chestertown Overview
        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    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.

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

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