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22 Properties
Map

22 Properties Available In Chestertown

  • Price-High To Low
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  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
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MD >Chestertown >
Market Insights
  • 860 & 870 HIGH ST, Chestertown, MD 21620
    16,977 SqFt
    1/92 92
    Price Dropped by $300K

    $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)
  • 21082 WYOMING AVE, Chestertown, MD 21620
    3 Beds4 Baths2,699 SqFt
    1/63 63
    Active

    $1,550,000

    21082 WYOMING AVE, Chestertown, MD 21620

    MLS# MDKE2005016

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 7961 QUAKER NECK RD, Chestertown, MD 21620
    5 Beds4 Baths4,167 SqFt
    1/95 95
    Pending

    $1,495,000

    7961 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005090

    Listed by Compass

    Bright MLS (BMLS)
  • 23393 CACAWAY FARM LN, Chestertown, MD 21620
    3 Beds4 Baths4,446 SqFt
    1/44 44
    Price Dropped by $100K

    $1,350,000

    23393 CACAWAY FARM LN, Chestertown, MD 21620

    MLS# MDKE2004002

    Listed by Gunther-McClary Real Estate

    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)
  • 209 RIVERSHORE RD, Chestertown, MD 21620
    2 Beds2 Baths1,401 SqFt
    1/3 3
    Coming Soon

    $815,000

    209 RIVERSHORE RD, Chestertown, MD 21620

    MLS# MDQA2013938

    Listed by Douglas Realty LLC

    Bright MLS (BMLS)
  • 24576 LANGFORD RD, Chestertown, MD 21620
    3 Beds3 Baths4,023 SqFt
    1/60 60
    Price Dropped by $46K

    $799,000

    24576 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2004906

    Listed by Maryland Heritage Properties

    Bright MLS (BMLS)
  • 206 S WATER ST, Chestertown, MD 21620
    4 Beds4 Baths2,008 SqFt
    1/56 56
    Coming Soon

    $699,000

    206 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2005362

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 7071 POMONA RD, Chestertown, MD 21620
    4 Beds4 Baths2,544 SqFt
    1/47 47
    New

    $665,000

    7071 POMONA RD, Chestertown, MD 21620

    MLS# MDKE2005364

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 136 TRUSLOW FARM LN, Chestertown, MD 21620
    3.01 Acres
    1/12 12
    Active

    $575,000

    136 TRUSLOW FARM LN, Chestertown, MD 21620

    MLS# MDQA2013478

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 5179 QUAKER NECK RD, Chestertown, MD 21620
    1 Bed1 Bath1,148 SqFt
    1/48 48
    Price Dropped by $20K

    $559,900

    5179 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005028

    Listed by Hyatt & Company Real Estate, LLC

    Bright MLS (BMLS)
  • 314 DEVON DR, Chestertown, MD 21620
    4 Beds4 Baths3,420 SqFt
    1/45 45
    Under Contract

    $499,900

    314 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2004946

    Listed by The Parker Group

    Bright MLS (BMLS)
  • 128 EDMORE RD, Chestertown, MD 21620
    4 Beds2 Baths2,568 SqFt
    1/59 59
    Active

    $425,000

    128 EDMORE RD, Chestertown, MD 21620

    MLS# MDQA2012546

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
  • 109 WILTON RD, Chestertown, MD 21620
    3 Beds2 Baths1,392 SqFt
    1/30 30
    Active

    $349,900

    109 WILTON RD, Chestertown, MD 21620

    MLS# MDQA2011782

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 110 FLYING CLOUD COURT, Chestertown, MD 21620
    3 Beds3 Baths1,856 SqFt
    1/17 17
    Active

    $349,900

    110 FLYING CLOUD COURT, Chestertown, MD 21620

    MLS# MDKE2004850

    Listed by Berkshire Hathaway HomeServices Homesale Realty

    Bright MLS (BMLS)
  • 925 ROUND TOP RD, Chestertown, MD 21620
    3 Beds1 Bath1,056 SqFt
    1/19 19
    Active

    $300,000

    925 ROUND TOP RD, Chestertown, MD 21620

    MLS# MDQA2013044

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 21317 PERSIMMON DR, Chestertown, MD 21620
    2 Beds1 Bath1,269 SqFt
    1/31 31
    Active

    $195,000

    21317 PERSIMMON DR, Chestertown, MD 21620

    MLS# MDKE2005356

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620
    16,977 SqFt
    1/30 30
    Active

    $425

    870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620

    MLS# MDKE2004432

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 870 HIGH ST #2, Chestertown, MD 21620
    16,977 SqFt
    1/35 35
    Active

    $18

    870 HIGH ST #2, Chestertown, MD 21620

    MLS# MDKE2003772

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 870 HIGH ST #2-3, Chestertown, MD 21620
    16,977 SqFt
    1/55 55
    Active

    $18

    870 HIGH ST #2-3, Chestertown, MD 21620

    MLS# MDKE2003776

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 870 HIGH ST #3, Chestertown, MD 21620
    16,977 SqFt
    1/36 36
    Active

    $18

    870 HIGH ST #3, Chestertown, MD 21620

    MLS# MDKE2003766

    Listed by Taylor Properties

    Bright MLS (BMLS)
  • 1

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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.