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    ZIP Code: 21620
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    150 Properties Available

    150 Properties Available

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    • Newest Listings
    • Beds (Most)
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    • Square Feet (Biggest)
    115 METCALF RD, Chestertown, MD 21620
    1/10
    New

    $259,900

    3 Beds2 Baths1,280 SqFt

    115 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006826

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    8999 ORCHARD DR, Chestertown, MD 21620
    1/74
    Coming Soon

    $824,900

    5 Beds4 Baths4,353 SqFt

    8999 ORCHARD DR, Chestertown, MD 21620

    MLS# MDKE2006786

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    2201 PONDTOWN RD, Chestertown, MD 21620
    1/24
    New

    $1,500

    3 Beds1 Bath1,272 SqFt

    2201 PONDTOWN RD, Chestertown, MD 21620

    MLS# MDQA2018024

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    21324 PERSIMMON DR, Chestertown, MD 21620
    1/21
    Open Sat 11AM-1PM
    3D

    $199,000

    2 Beds1 Bath1,232 SqFt

    21324 PERSIMMON DR, Chestertown, MD 21620

    MLS# MDKE2006816

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    107 CONLEY DR, Chestertown, MD 21620
    1/5
    Coming Soon

    $240,000

    3 Beds1 Bath1,140 SqFt

    107 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006828

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    7828 COUNTRY CLUB LN, Chestertown, MD 21620
    1/68
    Coming Soon

    $799,000

    3 Beds3 Baths2,857 SqFt

    7828 COUNTRY CLUB LN, Chestertown, MD 21620

    MLS# MDKE2006736

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    PRESTON LANE, Chestertown, MD 21620
    1/41
    Under Contract

    $525,000

    3 Beds3 Baths2,824 SqFt

    PRESTON LANE, Chestertown, MD 21620

    MLS# MDKE2006820

    Listed by Shoreline Realty

    Bright MLS (BMLS)
    109 CEDAR ST, Chestertown, MD 21620
    1/22
    Under Contract

    $325,000

    3 Beds3 Baths1,397 SqFt

    109 CEDAR ST, Chestertown, MD 21620

    MLS# MDKE2006792

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    123 HEATH RD, Chestertown, MD 21620
    1/4
    Coming Soon

    $349,000

    3 Beds2 Baths1,792 SqFt

    123 HEATH RD, Chestertown, MD 21620

    MLS# MDQA2017994

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    200 MANOR AVE, Chestertown, MD 21620
    1/34
    New

    $325,000

    4 Beds2 Baths2,198 SqFt

    200 MANOR AVE, Chestertown, MD 21620

    MLS# MDKE2006808

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    210 N QUEEN ST, Chestertown, MD 21620
    1/36
    New

    $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)
    121 METCALF RD, Chestertown, MD 21620
    1/10
    New

    $264,900

    3 Beds2 Baths3,920 Sqft Lot

    121 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006678

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    200-204 HIGH ST, Chestertown, MD 21620
    1/58
    New

    $2,300,000

    6,000 Sqft Lot

    200-204 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006810

    Listed by Taylor Properties

    Bright MLS (BMLS)
    233 MERGANSER DR, Chestertown, MD 21620
    1/13
    New

    $60,000

    0.5 Acres

    233 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2017912

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    903 WASHINGTON AVE #4, Chestertown, MD 21620
    1/9
    New

    $1,350

    0.8 Acres Lot

    903 WASHINGTON AVE #4, Chestertown, MD 21620

    MLS# MDKE2006832

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    305 ROOSEVELT DR, Chestertown, MD 21620
    New

    $60,000

    0.61 Acres

    305 ROOSEVELT DR, Chestertown, MD 21620

    MLS# MDKE2006830

    Listed by Taylor Properties

    Bright MLS (BMLS)
    104 MAPLE AVE #4, Chestertown, MD 21620
    1/12
    Active

    $1,920

    2 Beds2 Baths900 SqFt

    104 MAPLE AVE #4, Chestertown, MD 21620

    MLS# MDKE2006806

    Listed by Real Broker, LLC - Annapolis

    Bright MLS (BMLS)
    10720 FORESTON RD, Chestertown, MD 21620
    1/42
    Open Sat 11AM-1PM

    $335,000

    3 Beds2 Baths1,412 SqFt

    10720 FORESTON RD, Chestertown, MD 21620

    MLS# MDKE2006800

    Listed by Compass

    Bright MLS (BMLS)
    409 CALVERT ST, Chestertown, MD 21620
    1/9
    Active

    $155,000

    3 Beds2 Baths1,192 SqFt

    409 CALVERT ST, Chestertown, MD 21620

    MLS# MDKE2006794

    Listed by Chesapeake Real Estate Associates, LLC

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

    $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)
    9126 FAIRLEE RD, Chestertown, MD 21620
    1/20
    Active

    $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)
    896 WASHINGTON AVE, Chestertown, MD 21620
    1/34
    Active

    $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)
    351 CALVERT ST, Chestertown, MD 21620
    1/19
    Active

    $2,000

    3 Beds1 Bath1,122 SqFt

    351 CALVERT ST, Chestertown, MD 21620

    MLS# MDKE2006734

    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)
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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.
    IMG_20231010_020750 (1)
    R.I.C. Home Team @ Bennett Realty Solutions
    Reliable Investment Consulting
    +1(301) 823-5800
    support@richometeam.com
    6301 Ivy Ln, Greenbelt, MD, 20770-1402, USA

    Get My App

      • Home
        Property Management
        1. Request a Consultation
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        Featured Listings
        Blogs
      • Buy
        1. Request a Buyer Consultation
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        About
        1. About Us
        2. Meet the Team
        3. Contact Us
        4. Client Reviews
        Sold Listings
        Employee Resources
      • Sell
        1. Sell My Home
        2. Home Valuation
        Popular Areas
        1. Alexandria Overview
        2. Arlington Overview
        3. Washington Overview
        4. Baltimore Overview
        5. Silver Spring Overview
        6. Upper Marlboro Overview
        7. Hyattsville Overview
        8. Waldorf Overview
        Market Snapshot

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

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