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    Chestertown, MD
    Map
    2,677 Sold Properties

    2,677 Sold Properties

    The average price in the selected areas has remained stable. Learn more
    • Most Recent
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    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    129 TRAFFORD DR, Chestertown, MD 21620
    1/44

    $307,500

    $314,900

    2.3%
    3 Beds3 Baths3,001 SqFt

    129 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE116062

    Listed by Keller Williams Legacy

    Bright MLS (BMLS)
    7729 COUNTRY CLUB LN, Chestertown, MD 21620
    1/18

    $620,000

    $635,000

    2.4%
    3 Beds3 Baths2,280 SqFt

    7729 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2005552

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    304 HILLTOP LN, Chestertown, MD 21620
    1/31

    $215,000

    $209,900

    2.4%
    3 Beds3 Baths1,199 SqFt

    304 HILLTOP LN, Chestertown, MD 21620

    MLS# MDKE2005440

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    300 HILLTOP LN, Chestertown, MD 21620
    1/20

    $220,000

    $220,000

    3 Beds3 Baths1,200 SqFt

    300 HILLTOP LN, Chestertown, MD 21620

    MLS# MDKE2005004

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    9020 GEORGETOWN RD, Chestertown, MD 21620
    1/10

    $65,000

    $75,000

    13.3%
    2.36 Acres

    9020 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2005152

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    1814 PONDTOWN RD, Chestertown, MD 21620
    1/8

    $86,000

    $95,000

    9.5%
    3 Beds1 Bath973 SqFt

    1814 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2013018

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    104 OAK LEAF DR, Chestertown, MD 21620
    1/17

    $283,000

    $289,000

    2.1%
    3 Beds4 Baths1,840 SqFt

    104 OAK LEAF DR, Chestertown, MD 21620

    MLS# MDKE2004584

    Listed by Crown Homes Real Estate

    Bright MLS (BMLS)
    9816 FAIRLEE ROAD, Chestertown, MD 21620
    1/34

    $499,000

    $499,000

    3 Beds3 Baths1,624 SqFt

    9816 FAIRLEE ROAD, Chestertown, MD 21620

    MLS# MDKE2003632

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    7653 BROAD NECK RD, Chestertown, MD 21620
    1/39

    $375,000

    $375,000

    4 Beds3 Baths1,790 SqFt

    7653 BROAD NECK RD, Chestertown, MD 21620

    MLS# MDKE2005742

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    411 GREENWOOD AVE, Chestertown, MD 21620
    1/32

    $415,000

    $419,000

    1.0%
    3 Beds3 Baths1,676 SqFt

    411 GREENWOOD AVE, Chestertown, MD 21620

    MLS# MDKE2005824

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    5700 JOHNSONTOWN RD, Chestertown, MD 21620
    1/7

    $80,000

    $110,000

    27.3%
    3 Beds1 Bath1,144 SqFt

    5700 JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005562

    Listed by Tesla Realty Group, LLC

    Bright MLS (BMLS)
    120 SPEER RD, Chestertown, MD 21620
    1/9

    $1,100,000

    $1,250,000

    12.0%
    1.21 Acres Lot

    120 SPEER RD, Chestertown, MD 21620

    MLS# MDKE2005054

    Listed by Mackenzie Commercial R E SVCS, LLC

    Bright MLS (BMLS)
    517 HIGH ST, Chestertown, MD 21620
    1/51

    $361,500

    $389,900

    7.3%
    1,728 SqFt

    517 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005736

    Listed by L. C. Parker Real Estate

    Bright MLS (BMLS)
    492 PEAR TREE POINT RD, Chestertown, MD 21620
    1/73

    $850,000

    $875,000

    2.9%
    3 Beds2 Baths3,720 SqFt

    492 PEAR TREE POINT RD, Chestertown, MD 21620

    MLS# MDQA2015126

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    25195 LOVERS LN, Chestertown, MD 21620

    $350,000

    $350,000

    1 Bed1 Bath1,002 SqFt

    25195 LOVERS LN, Chestertown, MD 21620

    MLS# MDKE2005986

    Listed by Select Land & Homes, LLC

    Bright MLS (BMLS)
    101 BIRCH RUN RD, Chestertown, MD 21620
    1/38

    $475,000

    $499,999

    5.0%
    3 Beds2 Baths1,961 SqFt

    101 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2005810

    Listed by Remax Vision

    Bright MLS (BMLS)
    23393 CACAWAY FARM LN, Chestertown, MD 21620
    1/45

    $1,150,000

    $1,195,000

    3.8%
    3 Beds4 Baths4,446 SqFt

    23393 CACAWAY FARM LN, Chestertown, MD 21620

    MLS# MDKE2004002

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    109 2ND ST, Chestertown, MD 21620
    1/9

    $75,000

    $15,000

    400.0%
    1.8 Acres

    109 2ND ST, Chestertown, MD 21620

    MLS# MDQA2014918

    Listed by Ashland Auction Group LLC

    Bright MLS (BMLS)
    101 METCALF RD, Chestertown, MD 21620
    1/26

    $264,900

    $264,900

    3 Beds2 Baths1,280 SqFt

    101 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2005882

    Listed by Real Broker, LLC

    Bright MLS (BMLS)
    600 ROSIN DR, Chestertown, MD 21620
    1/35

    $413,300

    $415,000

    0.4%
    3 Beds2 Baths1,300 SqFt

    600 ROSIN DR, Chestertown, MD 21620

    MLS# MDQA2014896

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    302 ROSIN DR, Chestertown, MD 21620
    1/70

    $550,000

    $574,000

    4.2%
    5 Beds4 Baths3,877 SqFt

    302 ROSIN DR, Chestertown, MD 21620

    MLS# MDQA2015470

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    7483 SHORTALL ST, Chestertown, MD 21620
    1/26

    $287,500

    $290,000

    0.9%
    3 Beds2 Baths1,232 SqFt

    7483 SHORTALL ST, Chestertown, MD 21620

    MLS# MDKE2005616

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
    8951 ORCHARD DR, Chestertown, MD 21620
    1/47

    $700,000

    $695,000

    0.7%
    4 Beds4 Baths3,735 SqFt

    8951 ORCHARD DR, Chestertown, MD 21620

    MLS# MDKE2005836

    Listed by Rock Hall Properties Real Estate

    Bright MLS (BMLS)
    119 HIGH ST, Chestertown, MD 21620
    1/60

    $1,165,000

    $1,250,000

    6.8%
    5 Beds5 Baths4,409 SqFt

    119 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005728

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
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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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    +1(410) 220-4648 hello@justvybe.com

    502 Washington Ave #101 Towson, MD 21204, 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.
    zoom-png-color (1)

    Locally Owned & Operated

    VYBE Realty

    +1(410) 220-4648 hello@justvybe.com

    502 Washington Ave #101 Towson, MD 21204, USA
        Home
        Buy
        1. All Listings
        2. Mortgage Calculator
        3. Sold Listings
        4. Featured Listings
        5. Utilities
        Sell
        1. Sell My Home
        2. Home Valuation
        About
        1. Office Locations
        2. Reviews
        3. Meet the Team
        Contact
        Social
        1. VYBE Realty on Instagram
        2. VYBE Realty on Facebook
        3. VYBE Realty on TikTok
        4. VYBE Realty on Google
        Rentals

    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