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    City: Chestertown, MD
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    26 Properties Available In Chestertown

    26 Properties Available In Chestertown

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    MD >Chestertown >
    Market Insights
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    Address
    Price
    Beds
    Baths
    Area
    Status
    MLS®
    123 HEATH RD, Chestertown, MD 21620

    123 HEATH RD, Chestertown, MD 21620

    MLS# MDQA2017994 Listed by Chesapeake Real Estate Associates, LLC

    $349,000

    3
    2
    1,792 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDQA2017994
    22974 BAY SHORE RD, Chestertown, MD 21620

    22974 BAY SHORE RD, Chestertown, MD 21620

    MLS# MDKE2007106 Listed by Benson & Mangold, LLC

    $329,900

    2
    2
    1,440 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007106
    104 LINCOLN DR, Chestertown, MD 21620

    104 LINCOLN DR, Chestertown, MD 21620

    MLS# MDKE2007032 Listed by RE/MAX Executive

    $300,000

    3
    1
    960 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007032
    7415 WILKINS LN, Chestertown, MD 21620

    7415 WILKINS LN, Chestertown, MD 21620

    MLS# MDKE2007030 Listed by Doug Ashley Realtors, LLC

    $229,000

    3
    1
    936 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007030
    7464 SHORTALL ST, Chestertown, MD 21620

    7464 SHORTALL ST, Chestertown, MD 21620

    MLS# MDKE2006988 Listed by Chesapeake Real Estate Associates, LLC

    $304,000

    3
    2
    1,232 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006988
    216 BIRCH RUN RD, Chestertown, MD 21620

    216 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2006896 Listed by TTR Sotheby's International Realty

    $750,000

    3
    3
    2,176 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006896
    124 WILTON RD, Chestertown, MD 21620

    124 WILTON RD, Chestertown, MD 21620

    MLS# MDQA2018272 Listed by Doug Ashley Realtors, LLC

    $299,900

    3
    1
    1,056 SqFt
    Active
    Bright MLS (BMLS) MLS# MDQA2018272
    7982 RADCLIFFE RD, Chestertown, MD 21620

    7982 RADCLIFFE RD, Chestertown, MD 21620

    MLS# MDKE2006950 Listed by Doug Ashley Realtors, LLC

    $455,000

    2
    2
    1,904 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006950
    21324 PERSIMMON DR, Chestertown, MD 21620

    21324 PERSIMMON DR, Chestertown, MD 21620

    MLS# MDKE2006816 Listed by Benson & Mangold, LLC

    $179,900

    2
    1
    1,232 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDKE2006816
    200 MANOR AVE, Chestertown, MD 21620

    200 MANOR AVE, Chestertown, MD 21620

    MLS# MDKE2006808 Listed by TTR Sotheby's International Realty

    $325,000

    4
    2
    2,198 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006808
    25750 COLLINS AVE, Chestertown, MD 21620

    25750 COLLINS AVE, Chestertown, MD 21620

    MLS# MDKE2006546 Listed by Doug Ashley Realtors, LLC

    $448,000

    3
    2
    3,262 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDKE2006546
    8796 MARYLAND PKWY, Chestertown, MD 21620

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596 Listed by Coldwell Banker Chesapeake Real Estate Company

    $1,495,000

    9
    7
    4,776 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006596
    213 BYFORD DR, Chestertown, MD 21620

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026 Listed by Doug Ashley Realtors, LLC

    $372,000

    4
    2
    1,277 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006026
    956 WASHINGTON AVE, Chestertown, MD 21620

    956 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006394 Listed by Doug Ashley Realtors, LLC

    $275,000

    3
    1
    1,248 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006394
    103 SUTTON WAY, Chestertown, MD 21620

    103 SUTTON WAY, Chestertown, MD 21620

    MLS# MDKE2006344 Listed by TTR Sotheby's International Realty

    $509,000

    5
    4
    3,816 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006344
    117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

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

    MLS# MDKE2006158 Listed by TTR Sotheby's International Realty

    $1,500,000

    7
    5
    5,400 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006158
    117 WATER ST N #1A, Chestertown, MD 21620

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

    MLS# MDKE2006162 Listed by TTR Sotheby's International Realty

    $685,000

    3
    3
    3,000 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006162
    117 WATER ST N #2A, Chestertown, MD 21620

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

    MLS# MDKE2006166 Listed by TTR Sotheby's International Realty

    $375,000

    2
    1
    787 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006166
    117 WATER ST N #2B, Chestertown, MD 21620

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

    MLS# MDKE2006168 Listed by TTR Sotheby's International Realty

    $350,000

    1
    1
    850 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006168
    117 WATER ST N #1B, Chestertown, MD 21620

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

    MLS# MDKE2006164 Listed by TTR Sotheby's International Realty

    $200,000

    1
    1
    700 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006164
    204 DOUBLE CREEK RD, Chestertown, MD 21620

    204 DOUBLE CREEK RD, Chestertown, MD 21620

    MLS# MDQA2015996 Listed by Doug Ashley Realtors, LLC

    $545,000

    3
    3
    2,927 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDQA2015996
    218 CAMELOT DR, Chestertown, MD 21620

    218 CAMELOT DR, Chestertown, MD 21620

    MLS# MDKE2005982 Listed by Coldwell Banker Realty

    $499,999

    5
    4
    3,932 SqFt
    Under Contract
    Bright MLS (BMLS) MLS# MDKE2005982
    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2005768 Listed by Gunther-McClary Real Estate

    $1,459,000

    3
    3
    2,231 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2005768
    105 HIGH ST, Chestertown, MD 21620

    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
    Bright MLS (BMLS) MLS# MDKE2005890
    • 1
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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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    Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty
    Mikeshia Lindsey
    License ID: 5011891 and RS-0039676
    +1(443) 397-1773
    moveswithmikeshia@gmail.com
    Main St, Warwick, MD 21912, USA

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    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.
    site logo
    Chesapeake Real Estate Associates, LLC and Century 21 Gold Key Realty
    Mikeshia Lindsey
    License ID: 5011891 and RS-0039676
    +1(443) 397-1773
    moveswithmikeshia@gmail.com
    Main St, Warwick, MD 21912, USA

    Get My App

      • Home
        Rent
        1. Rental Listings
      • Buy
        1. All Listings
        2. Featured Listings
        3. Calculator
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Market Snapshot

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

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