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    ZIP Code: 21620
    Map
    148 Properties Available In 21620

    148 Properties Available In 21620

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    • Newest Listings
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    MD >21620 >
    Market Insights
    9126 FAIRLEE RD, Chestertown, MD 21620
    1/20
    Open Sat 11AM-1PM

    $344,000

    3 Beds2 Baths1,216 SqFt

    9126 FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2006764

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    210 N QUEEN ST, Chestertown, MD 21620
    1/12
    Coming Soon

    $735,000

    4 Beds3 Baths2,730 SqFt

    210 N QUEEN ST, Chestertown, MD 21620

    MLS# MDKE2006744

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    103 METCALF RD, Chestertown, MD 21620
    1/22
    Open Tue 2PM-6PM

    $259,900

    3 Beds2 Baths1,280 SqFt

    103 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006446

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    105 HIGH ST, Chestertown, MD 21620
    1/48
    Open Sat 10AM-12PM

    $1,245,500

    5 Beds5 Baths3,243 SqFt

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005890

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    7989 QUAKER NECK RD, Chestertown, MD 21620
    1/61
    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)
    521 N KENT ST, Chestertown, MD 21620
    Under Contract

    $385,000

    3 Beds2 Baths1,934 SqFt

    521 N KENT ST, Chestertown, MD 21620

    MLS# MDKE2006784

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    7680 COUNTRY CLUB LN, Chestertown, MD 21620
    1/43
    New

    $885,000

    5 Beds4 Baths2,639 SqFt

    7680 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2006758

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    896 WASHINGTON AVE, Chestertown, MD 21620
    1/34
    New

    $325,000

    3 Beds1 Bath1,000 SqFt

    896 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2006750

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    103 MAPLE AVE, Chestertown, MD 21620
    1/13
    Under Contract

    $615,000

    4 Beds3 Baths4,536 SqFt

    103 MAPLE AVE, Chestertown, MD 21620

    MLS# MDKE2006676

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    105 N WATER ST #2, Chestertown, MD 21620
    1/49
    Active

    $475,000

    2 Beds2 Baths1,011 SqFt

    105 N WATER ST #2, Chestertown, MD 21620

    MLS# MDKE2006680

    Listed by Northrop Realty

    Bright MLS (BMLS)
    22481 GOOSE HOLLOW DR, Chestertown, MD 21620
    1/88
    Active

    $279,900

    3 Beds2 Baths1,296 SqFt

    22481 GOOSE HOLLOW DR, Chestertown, MD 21620

    MLS# MDKE2006682

    Listed by Keller Williams Legacy

    Bright MLS (BMLS)
    25750 COLLINS AVE, Chestertown, MD 21620
    1/50
    Active

    $468,000

    3 Beds2 Baths3,262 SqFt

    25750 COLLINS AVE, Chestertown, MD 21620

    MLS# MDKE2006546

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    201 RIVER RD, Chestertown, MD 21620
    1/46
    Under Contract

    $629,900

    3 Beds2 Baths2,430 SqFt

    201 RIVER RD, Chestertown, MD 21620

    MLS# MDQA2017684

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    101 S MILL ST, Chestertown, MD 21620
    1/39
    Active

    $515,000

    2 Beds3 Baths1,476 SqFt

    101 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006674

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    517 ROUND TOP RD, Chestertown, MD 21620
    1/28
    Price Dropped by $25K

    $324,900

    3 Beds1 Bath1,248 SqFt

    517 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2017680

    Listed by Keller Williams Flagship

    Bright MLS (BMLS)
    104 CONLEY DR, Chestertown, MD 21620
    1/27
    Price Dropped by $7K

    $239,900

    3 Beds2 Baths1,280 SqFt

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686

    Listed by Cummings & Co. Realtors

    Bright MLS (BMLS)
    221 DUTCHESS RD, Chestertown, MD 21620
    Under Contract

    $228,000

    3 Beds2 Baths2,260 SqFt

    221 DUTCHESS RD, Chestertown, MD 21620

    MLS# MDQA2017670

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    202 ROYSTON SHORES RD, Chestertown, MD 21620
    1/72
    Under Contract

    $1,200,000

    4 Beds3 Baths2,292 SqFt

    202 ROYSTON SHORES RD, Chestertown, MD 21620

    MLS# MDQA2017462

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    10572 WATONGA RD, Chestertown, MD 21620
    1/25
    Under Contract

    $325,000

    3 Beds2 Baths1,404 SqFt

    10572 WATONGA RD, Chestertown, MD 21620

    MLS# MDKE2006644

    Listed by Serhant

    Bright MLS (BMLS)
    23264 CLARISSA RD, Chestertown, MD 21620
    1/30
    Under Contract

    $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)
    104 ACORN DR, Chestertown, MD 21620
    1/26
    Active

    $284,900

    3 Beds3 Baths1,900 SqFt

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668

    Listed by Cross Street Realtors LLC

    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)
    8796 MARYLAND PKWY, Chestertown, MD 21620
    1/60
    Active

    $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)
    110 PROSPECT ST, Chestertown, MD 21620
    1/6
    Price Dropped by $10K

    $89,900

    3 Beds2 Baths2,210 SqFt

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
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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
      • Home
        Neighborhoods
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        10. New Market Listings
        11. Spring Ridge Listings
        12. Thurmont Listings
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        Market Snapshot
      • Buy
        1. All Listings
        2. Featured Listings
        Rent
        1. Rental Listings
      • Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        About
        1. About Us
        2. Contact Us
        3. Reviews
        4. Blogs
        5. Book A Free Virtual Consultation

    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.