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    Neighborhood: Chestertown, Chestertown, MD
    Listing Status: Active
    Map
    57 Properties Available In Chestertown

    57 Properties Available In Chestertown

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    MD >Chestertown >Chestertown >
    Market Insights
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    Address
    Price
    Beds
    Baths
    Area
    Status
    MLS®
    223 MOUNT VERNON AVE, Chestertown, MD 21620

    223 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2007080 Listed by Chesapeake Real Estate Associates, LLC

    $200,000

    4
    1
    1,816 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007080
    123 TRAFFORD DR, Chestertown, MD 21620

    123 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006970 Listed by Chesapeake Real Estate Associates, LLC

    $375,000

    4
    3
    2,504 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006970
    106 QUEEN ST S, Chestertown, MD 21620

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152 Listed by Chesapeake Real Estate Associates, LLC

    $829,000

    3
    4
    2,472 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006152
    302 PARK ROW #BASEMENT OFFICE 3, Chestertown, MD 21620

    302 PARK ROW #BASEMENT OFFICE 3, Chestertown, MD 21620

    MLS# MDKE2006008 Listed by Chesapeake Real Estate Associates, LLC

    $445

    --
    --
    --
    Active
    Bright MLS (BMLS) MLS# MDKE2006008
    115 METCALF RD, Chestertown, MD 21620

    115 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006826 Listed by Real Broker, LLC - Chester

    $259,900

    3
    2
    1,280 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006826
    104 LINCOLN DR, Chestertown, MD 21620

    104 LINCOLN DR, Chestertown, MD 21620

    MLS# MDKE2007032 Listed by RE/MAX Executive

    $295,000

    3
    1
    960 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2007032
    115 CHESTER ARMS DR, Chestertown, MD 21620

    115 CHESTER ARMS DR, Chestertown, MD 21620

    MLS# MDKE2006958 Listed by Samson Properties

    $263,000

    3
    2
    1,140 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006958
    300 AND 302 S MILL ST, Chestertown, MD 21620

    300 AND 302 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006850 Listed by Coldwell Banker Chesapeake Real Estate Company

    $1,195,000

    2
    1
    806 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006850
    101 S COLLEGE AVE, Chestertown, MD 21620

    101 S COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006918 Listed by Doug Ashley Realtors, LLC

    $359,000

    2
    2
    1,036 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006918
    117 N WATER ST #3B, Chestertown, MD 21620

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

    MLS# MDKE2006968 Listed by Coldwell Banker Chesapeake Real Estate Company

    $295,000

    1
    1
    --
    Active
    Bright MLS (BMLS) MLS# MDKE2006968
    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
    129 TRAFFORD DR, Chestertown, MD 21620

    129 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006878 Listed by Elevated Real Estate Solutions

    $480,000

    3
    3
    3,176 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006878
    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
    121 METCALF RD, Chestertown, MD 21620

    121 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006678 Listed by Real Broker, LLC - Chester

    $264,900

    3
    2
    3,920 Sqft Lot
    Active
    Bright MLS (BMLS) MLS# MDKE2006678
    104 CONLEY DR, Chestertown, MD 21620

    104 CONLEY DR, Chestertown, MD 21620

    MLS# MDKE2006686 Listed by Cummings & Co. Realtors

    $239,900

    3
    2
    1,280 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006686
    104 ACORN DR, Chestertown, MD 21620

    104 ACORN DR, Chestertown, MD 21620

    MLS# MDKE2006668 Listed by Cross Street Realtors LLC

    $275,000

    3
    3
    1,900 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006668
    234 N COLLEGE AVE, Chestertown, MD 21620

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670 Listed by Cummings & Co Realtors

    $85,000

    2
    1
    1,296 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006670
    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
    226 S WATER ST, Chestertown, MD 21620

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2006354 Listed by Gunther-McClary Real Estate

    $898,000

    3
    4
    2,172 SqFt
    Active
    Bright MLS (BMLS) MLS# MDKE2006354
    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
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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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    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