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38 Properties
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38 Properties Available In Chestertown

  • Price-High To Low
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MD >Chestertown >Chestertown >
Market Insights
  • 860 & 870 HIGH ST, Chestertown, MD 21620
    16,977 SqFt
    1/92 92
    Active

    $2,400,000

    860 & 870 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2003850

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 870 HIGH ST, Chestertown, MD 21620
    16,977 SqFt
    1/72 72
    Active

    $1,870,000

    870 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2004140

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • LITTLE HARBOR WAY #1, Chestertown, MD 21620
    3 Beds3 Baths2,315 SqFt
    1/22 22
    Active

    $1,459,000

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2004992

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 105 HIGH ST, Chestertown, MD 21620
    5 Beds5 Baths2,688 SqFt
    1/52 52
    Active

    $1,395,500

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005002

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 120 SPEER RD, Chestertown, MD 21620
    52,708 SqFt
    1/9 9
    Active

    $1,250,000

    120 SPEER RD, Chestertown, MD 21620

    MLS# MDKE2005054

    Listed by Mackenzie Commercial R E SVCS, LLC

    Bright MLS (BMLS)
  • 329 HIGH ST, Chestertown, MD 21620
    3,996 SqFt
    1/19 19
    Active

    $1,250,000

    329 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005172

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 206 CANNON ST, Chestertown, MD 21620
    1.56 Acres
    1/9 9
    Active

    $1,150,000

    206 CANNON ST, Chestertown, MD 21620

    MLS# MDKE2003620

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • 226 S WATER ST, Chestertown, MD 21620
    3 Beds4 Baths3,782 SqFt
    1/22 22
    Active

    $998,000

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2004940

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 515 WASHINGTON AVE, Chestertown, MD 21620
    42,200 SqFt
    1/4 4
    Active

    $899,000

    515 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2000776

    Listed by EShore

    Bright MLS (BMLS)
  • 860 HIGH ST, Chestertown, MD 21620
    3,114 SqFt
    1/38 38
    Active

    $860,000

    860 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2004138

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 201 N LYNCHBURG ST, Chestertown, MD 21620
    4,342 SqFt
    1/13 13
    Price Dropped by $145K

    $850,000

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2005278

    Listed by RE/MAX Associates-Hockessin

    Bright MLS (BMLS)
  • 200 WASHINGTON AVE, Chestertown, MD 21620
    4 Beds4 Baths9,100 SqFt
    1/35 35
    Active

    $795,000

    200 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2005538

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 212 LANDING LN, Chestertown, MD 21620
    3 Beds4 Baths
    1/36 36
    Active

    $759,000

    212 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2004782

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 117 N WATER ST #1A, Chestertown, MD 21620
    3 Beds3 Baths
    1/28 28
    Active

    $725,000

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

    MLS# MDKE2004206

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 206 S WATER ST, Chestertown, MD 21620
    4 Beds4 Baths2,008 SqFt
    1/51 51
    Active

    $648,750

    206 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2005362

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 103 ADELA WAY, Chestertown, MD 21620
    4 Beds4 Baths10,295 SqFt
    1/90 90
    Price Dropped by $20K

    $595,000

    103 ADELA WAY, Chestertown, MD 21620

    MLS# MDKE2005594

    Listed by Douglas Realty LLC

    Bright MLS (BMLS)
  • 251 DEVON DR, Chestertown, MD 21620
    3 Beds3 Baths3,935 SqFt
    1/54 54
    Active

    $595,000

    251 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2005536

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 116 HARLAN LOOP, Chestertown, MD 21620
    5 Beds4 Baths11,477 SqFt
    1/21 21
    Price Dropped by $9K

    $529,000

    116 HARLAN LOOP, Chestertown, MD 21620

    MLS# MDKE2005610

    Listed by Samson Properties

    Bright MLS (BMLS)
  • 515 N KENT ST, Chestertown, MD 21620
    4 Beds2 Baths15,000 SqFt
    1/37 37
    New

    $509,900

    515 N KENT ST, Chestertown, MD 21620

    MLS# MDKE2005592

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 201 BIRCH RUN RD, Chestertown, MD 21620
    3 Beds2 Baths1,588 SqFt
    1/23 23
    Price Dropped by $25K

    $470,000

    201 BIRCH RUN RD, Chestertown, MD 21620

    MLS# MDKE2005380

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 117 WATER ST N #2A, Chestertown, MD 21620
    2 Beds1 Bath787 SqFt
    1/28 28
    Active

    $399,000

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

    MLS# MDKE2003742

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 110 FLYING CLOUD COURT, Chestertown, MD 21620
    3 Beds3 Baths4,000 SqFt
    1/17 17
    Price Dropped by $9K

    $340,000

    110 FLYING CLOUD COURT, Chestertown, MD 21620

    MLS# MDKE2004850

    Listed by Berkshire Hathaway HomeServices Homesale Realty

    Bright MLS (BMLS)
  • 108 S KENT ST, Chestertown, MD 21620
    1 Bed2 Baths936 SqFt
    1/19 19
    Price Dropped by $10K

    $315,000

    108 S KENT ST, Chestertown, MD 21620

    MLS# MDKE2005496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 100 METCALF RD, Chestertown, MD 21620
    3 Beds2 Baths5,914 SqFt
    1/17 17
    New

    $255,000

    100 METCALF RD, Chestertown, MD 21620

    MLS# MDKE2005634

    Listed by Bayside Realty

    Bright MLS (BMLS)
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Carelly Realty Group_combo1_1 CROP
      Properties
      1. Map Search
      2. Exclusive Listings
      3. Open Houses
      4. Newest Listings
      5. All Properties
      6. Sold Listings
      Sell
      1. Sell A Home
      2. Seller Questionnaire
      3. Home Valuation
      4. Market Reports
      Buy
      1. Buy A Home
      2. Financing
      3. Buyer Questionnaire
      4. Calculator
      5. Email Listing Alerts
      Services
      1. Home Equity Building Tools
      2. Renter Resources
      3. Available Services
      Special Offers
      1. Seller Book
      2. For Sale By Owner Book
      3. Expired Listing Book
      4. Foreclosure Book
      5. First Time Home Buyer Book
      6. Home Buyer Book
      7. Digital Magazine
      8. Home Sweet Home Magazine
      Market News
      1. Real Estate Blog
      Why Us
      1. About Us
      2. Client Reviews
      Connect
Carelly Realty Group

Kelly & Carl Robinson License ID: 1968923

+1(973) 500-3253 info@carellyrealty.com

549 Millburn Ave, Short Hills, NJ, 07078-3330, USA

NEW JERSEY LUXURY REAL ESTATE AGENTS

Real Estate Website Design by Bullsai

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Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.
Carelly Realty Group_combo1_1 CROP
      Properties
      1. Map Search
      2. Exclusive Listings
      3. Open Houses
      4. Newest Listings
      5. All Properties
      6. Sold Listings
      Sell
      1. Sell A Home
      2. Seller Questionnaire
      3. Home Valuation
      4. Market Reports
      Buy
      1. Buy A Home
      2. Financing
      3. Buyer Questionnaire
      4. Calculator
      5. Email Listing Alerts
      Services
      1. Home Equity Building Tools
      2. Renter Resources
      3. Available Services
      Special Offers
      1. Seller Book
      2. For Sale By Owner Book
      3. Expired Listing Book
      4. Foreclosure Book
      5. First Time Home Buyer Book
      6. Home Buyer Book
      7. Digital Magazine
      8. Home Sweet Home Magazine
      Market News
      1. Real Estate Blog
      Why Us
      1. About Us
      2. Client Reviews
      Connect
Carelly Realty Group

Kelly & Carl Robinson License ID: 1968923

+1(973) 500-3253 info@carellyrealty.com

549 Millburn Ave, Short Hills, NJ, 07078-3330, USA

NEW JERSEY LUXURY REAL ESTATE AGENTS

Real Estate Website Design by Bullsai

Get My App

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

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.