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    ZIP Code: 21620
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    156 Properties Available

    156 Properties Available

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    • Price-High To Low
    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
    • Square Feet (Biggest)
    7464 SHORTALL ST, Chestertown, MD 21620
    1/32
    New

    $304,000

    3 Beds2 Baths1,232 SqFt

    7464 SHORTALL ST, Chestertown, MD 21620

    MLS# MDKE2006988

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    212 WASHINGTON AVE, Chestertown, MD 21620
    Coming Soon

    $675,000

    5 Beds3 Baths2,838 SqFt

    212 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2007016

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    302 S MILL ST, Chestertown, MD 21620
    1/17
    New

    $1,195,000

    2 Beds1 Bath806 SqFt

    302 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006850

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    8184 ROCK HALL RD, Chestertown, MD 21620
    1/36
    New

    $38,200,000

    4 Beds2 Baths1,053.61 Acres

    8184 ROCK HALL RD, Chestertown, MD 21620

    MLS# MDKE2007006

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    240 ROUND TOP RD, Chestertown, MD 21620
    1/30
    Under Contract

    $295,000

    3 Beds2 Baths1,132 SqFt

    240 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2018166

    Listed by Clark & Co Realty, LLC

    Bright MLS (BMLS)
    22427 CROSS RD, Chestertown, MD 21620
    1/16
    Under Contract

    $1,600

    3 Beds1 Bath1,008 SqFt

    22427 CROSS RD, Chestertown, MD 21620

    MLS# MDKE2007002

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    101 S COLLEGE AVE, Chestertown, MD 21620
    1/35
    New

    $369,000

    2 Beds2 Baths1,036 SqFt

    101 S COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006918

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    217 EDMORE RD, Chestertown, MD 21620
    Coming Soon

    $345,000

    3 Beds2 Baths1,398 SqFt

    217 EDMORE RD, Chestertown, MD 21620

    MLS# MDQA2018386

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    22400 GREAT OAK LANDING RD., Chestertown, MD 21620
    1/61
    New

    $649,000

    4 Beds3 Baths2,864 SqFt

    22400 GREAT OAK LANDING RD., Chestertown, MD 21620

    MLS# MDKE2006946

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    1003 TWIN CT, Chestertown, MD 21620
    1/43
    New

    $524,900

    3 Beds3 Baths2,076 SqFt

    1003 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006974

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    117 N WATER ST #3B, Chestertown, MD 21620
    1/18
    Active

    $295,000

    1 Bed1 Bath

    117 N WATER ST #3B, Chestertown, MD 21620

    MLS# MDKE2006968

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    104 CHURCH ALY, Chestertown, MD 21620
    1/34
    Under Contract

    $440,000

    2 Beds2 Baths1,058 SqFt

    104 CHURCH ALY, Chestertown, MD 21620

    MLS# MDKE2006900

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    124 WILTON RD, Chestertown, MD 21620
    1/26
    Active

    $299,900

    3 Beds1 Bath1,056 SqFt

    124 WILTON RD, Chestertown, MD 21620

    MLS# MDQA2018272

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    216 BIRCH RUN RD, Chestertown, MD 21620
    1/52
    Active

    $750,000

    3 Beds3 Baths2,176 SqFt

    216 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2006896

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    23208 BUCK NECK RD, Chestertown, MD 21620
    1/35
    Active

    $349,900

    3 Beds3 Baths1,650 SqFt

    23208 BUCK NECK RD, Chestertown, MD 21620

    MLS# MDKE2006980

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    249 ISLAND LARK WAY, Chestertown, MD 21620
    1/17
    Under Contract

    $259,900

    3 Beds3 Baths1,420 SqFt

    249 ISLAND LARK WAY, Chestertown, MD 21620

    MLS# MDKE2006972

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    123 TRAFFORD DR, Chestertown, MD 21620
    Active

    $375,000

    4 Beds3 Baths2,504 SqFt

    123 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006970

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    115 CHESTER ARMS DR, Chestertown, MD 21620
    Coming Soon

    $263,000

    3 Beds2 Baths1,140 SqFt

    115 CHESTER ARMS DR, Chestertown, MD 21620

    MLS# MDKE2006958

    Listed by Samson Properties

    Bright MLS (BMLS)
    10540 TONOPAH RD, Chestertown, MD 21620
    1/21
    Active

    $279,000

    3 Beds2 Baths1,404 SqFt

    10540 TONOPAH RD, Chestertown, MD 21620

    MLS# MDKE2006880

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    8630 ELM RD, Chestertown, MD 21620
    1/45
    Price Dropped by $20K

    $424,900

    5 Beds3 Baths1,936 SqFt

    8630 ELM RD, Chestertown, MD 21620

    MLS# MDKE2006914

    Listed by Save 6, Incorporated

    Bright MLS (BMLS)
    7982 RADCLIFFE RD, Chestertown, MD 21620
    1/37
    Active

    $478,000

    2 Beds2 Baths1,904 SqFt

    7982 RADCLIFFE RD, Chestertown, MD 21620

    MLS# MDKE2006950

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    122 SPEER RD #5, Chestertown, MD 21620
    Active

    $5,017

    1.68 Acres Lot

    122 SPEER RD #5, Chestertown, MD 21620

    MLS# MDKE2006936

    Listed by Mackenzie Commercial R E SVCS, LLC

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

    $350,000

    0.22 Acres

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006940

    Listed by Taylor Properties

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

    $450,000

    0.29 Acres

    CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006944

    Listed by Taylor Properties

    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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    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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        4. Submit a Maintenance Request
        5. Owner & Manager Login
        6. Available Properties for Rent
        Featured Listings
        Blogs
      • Buy
        1. Request a Buyer Consultation
        2. Search for Homes
        3. Mortgage Calculator
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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