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

    58 Properties Available In Chestertown

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    • Price-Low To High
    • Newest Listings
    • Beds (Most)
    • Baths (Most)
    • Year Built (Newest)
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    MD >Chestertown >Chestertown >
    Market Insights
    213 BYFORD DR, Chestertown, MD 21620
    1/39
    New

    $380,000

    4 Beds2 Baths1,277 SqFt

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    100 PROSPECT ST, Chestertown, MD 21620
    1/21
    New

    $215,000

    3 Beds1 Bath1,373 SqFt

    100 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006544

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    522 HIGH ST, Chestertown, MD 21620
    1/15
    New

    $450,000

    2 Beds3 Baths1,518 SqFt

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
    110 S QUEEN ST, Chestertown, MD 21620
    1/30
    Active

    $525,000

    3 Beds2 Baths1,785 SqFt

    110 S QUEEN ST, Chestertown, MD 21620

    MLS# MDKE2006520

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
    102 FLYING CLOUD DR, Chestertown, MD 21620
    1/41
    Active

    $339,900

    3 Beds3 Baths1,896 SqFt

    102 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006586

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
    107 FLYING CLOUD DR, Chestertown, MD 21620
    1/51
    Active

    $395,000

    5 Beds4 Baths2,534 SqFt

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510

    Listed by CENTURY 21 New Millennium

    Bright MLS (BMLS)
    304 HADAWAY DR, Chestertown, MD 21620
    1/38
    Price Dropped by $7K
    3D

    $322,500

    4 Beds2 Baths1,325 SqFt

    304 HADAWAY DR, Chestertown, MD 21620

    MLS# MDKE2006482

    Listed by Redfin Corporation

    Bright MLS (BMLS)
    407 HIGH ST, Chestertown, MD 21620
    1/57
    Price Dropped by $30K

    $798,000

    3 Beds5 Baths3,047 SqFt

    407 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    103 TRAFFORD DR, Chestertown, MD 21620
    1/66
    Price Dropped by $30K

    $419,900

    3 Beds3 Baths1,944 SqFt

    103 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
    103 METCALF RD, Chestertown, MD 21620
    1/22
    Active

    $259,900

    3 Beds2 Baths1,280 SqFt

    103 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2006446

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    226 S WATER ST, Chestertown, MD 21620
    1/31
    Active

    $898,000

    3 Beds4 Baths2,172 SqFt

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2006354

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
    103 SUTTON WAY, Chestertown, MD 21620
    1/53
    Active

    $550,000

    5 Beds4 Baths3,816 SqFt

    103 SUTTON WAY, Chestertown, MD 21620

    MLS# MDKE2006344

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    106 QUEEN ST S, Chestertown, MD 21620
    1/92
    Active

    $865,000

    3 Beds4 Baths2,472 SqFt

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
    104 FLYING CLOUD DR, Chestertown, MD 21620
    1/30
    Price Dropped by $5K

    $394,900

    5 Beds4 Baths2,535 SqFt

    104 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006212

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    108 PINE ST, Chestertown, MD 21620
    Price Dropped by $27K

    $115,000

    3 Beds1 Bath910 SqFt

    108 PINE ST, Chestertown, MD 21620

    MLS# MDKE2006322

    Listed by Real Broker, LLC - Chester

    Bright MLS (BMLS)
    139 PROSPECT ST, Chestertown, MD 21620
    1/28
    Active

    $225,000

    3 Beds1 Bath1,200 SqFt

    139 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006250

    Listed by Redfin Corp

    Bright MLS (BMLS)
    202 WALDO DR, Chestertown, MD 21620
    1/28
    Price Dropped by $49K

    $340,000

    3 Beds2 Baths2,055 SqFt

    202 WALDO DR, Chestertown, MD 21620

    MLS# MDKE2006260

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
    117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
    1/73
    Active

    $1,600,000

    7 Beds5 Baths5,400 SqFt

    117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

    MLS# MDKE2006158

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #1A, Chestertown, MD 21620
    1/46
    Active

    $685,000

    3 Beds3 Baths3,000 SqFt

    117 WATER ST N #1A, Chestertown, MD 21620

    MLS# MDKE2006162

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #2A, Chestertown, MD 21620
    1/24
    Active

    $375,000

    2 Beds1 Bath787 SqFt

    117 WATER ST N #2A, Chestertown, MD 21620

    MLS# MDKE2006166

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #2B, Chestertown, MD 21620
    1/23
    Active

    $350,000

    1 Bed1 Bath850 SqFt

    117 WATER ST N #2B, Chestertown, MD 21620

    MLS# MDKE2006168

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    117 WATER ST N #1B, Chestertown, MD 21620
    1/20
    Active

    $200,000

    1 Bed1 Bath700 SqFt

    117 WATER ST N #1B, Chestertown, MD 21620

    MLS# MDKE2006164

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
    110 TRAFFORD DR, Chestertown, MD 21620
    1/22
    Price Dropped by $15K

    $450,000

    4 Beds3 Baths2,880 SqFt

    110 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2005964

    Listed by RE/MAX Advantage Realty

    Bright MLS (BMLS)
    218 CAMELOT DR, Chestertown, MD 21620
    1/45
    Price Dropped by $10K

    $499,999

    5 Beds4 Baths3,932 SqFt

    218 CAMELOT DR, Chestertown, MD 21620

    MLS# MDKE2005982

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
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        Market Snapshot
    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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    Bayside Realty
    Dale Hunter Jr
    +1(443) 829-5828
    dalehunterjr@baysiderealtymd.com
    23458 Scotts Ln, St Michaels, MD, 21663, USA
        Home
        Buy
        1. All Listings
        2. Featured Listings
        Sell
        1. Sell My Home
        2. Home Valuation
        3. Recent Sold
        Rent
        1. Rental Listings
        Featured Areas
        1. Easton Overview
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        5. Saint Michaels Overview
        6. Ridgely Overview
        7. Berlin Overview
        About
        1. My Team
        2. About Us
        3. Contact Us
        4. Reviews
        Market Snapshot
    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.

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

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