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16 Properties
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16 Properties Available In Chestertown

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MD >Chestertown >Chestertown >
Market Insights
  • LITTLE HARBOR WAY #1, Chestertown, MD 21620
    4 Beds4 Baths3,540 SqFt
    1/29 29
    Active

    $1,800,000

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2004992

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
    7 Beds5 Baths5,400 SqFt
    1/73 73
    Active

    $1,600,000

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

    MLS# MDKE2006158

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • LITTLE HARBOR WAY #1, Chestertown, MD 21620
    3 Beds3 Baths2,231 SqFt
    1/25 25
    Active

    $1,459,000

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2005768

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 105 HIGH ST, Chestertown, MD 21620
    5 Beds5 Baths3,243 SqFt
    1/48 48
    Price Dropped by $100K

    $1,295,500

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005890

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 231 RICHARD DR, Chestertown, MD 21620
    5 Beds3 Baths2,956 SqFt
    1/51 51
    Pending

    $1,150,000

    231 RICHARD DR, Chestertown, MD 21620

    MLS# MDKE2005900

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 117 WATER ST N #1A, Chestertown, MD 21620
    3 Beds3 Baths3,000 SqFt
    1/46 46
    Active

    $685,000

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

    MLS# MDKE2006162

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 103 SUTTON WAY, Chestertown, MD 21620
    5 Beds4 Baths3,816 SqFt
    1/53 53
    Active

    $550,000

    103 SUTTON WAY, Chestertown, MD 21620

    MLS# MDKE2006344

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 101 S MILL ST, Chestertown, MD 21620
    2 Beds3 Baths1,476 SqFt
    1/39 39
    Coming Soon

    $515,000

    101 S MILL ST, Chestertown, MD 21620

    MLS# MDKE2006674

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 218 CAMELOT DR, Chestertown, MD 21620
    5 Beds4 Baths3,932 SqFt
    1/45 45
    Price Dropped by $10K

    $499,999

    218 CAMELOT DR, Chestertown, MD 21620

    MLS# MDKE2005982

    Listed by Coldwell Banker Realty

    Bright MLS (BMLS)
  • 311 DEVON DR, Chestertown, MD 21620
    4 Beds3 Baths3,504 SqFt
    1/41 41
    Price Dropped by $24K

    $475,000

    311 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2005930

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 110 TRAFFORD DR, Chestertown, MD 21620
    4 Beds3 Baths2,880 SqFt
    1/22 22
    Price Dropped by $15K

    $450,000

    110 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2005964

    Listed by RE/MAX Advantage Realty

    Bright MLS (BMLS)
  • 213 BYFORD DR, Chestertown, MD 21620
    4 Beds2 Baths1,277 SqFt
    1/39 39
    Active

    $380,000

    213 BYFORD DR, Chestertown, MD 21620

    MLS# MDKE2006026

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 117 WATER ST N #2A, Chestertown, MD 21620
    2 Beds1 Bath787 SqFt
    1/24 24
    Active

    $375,000

    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 Bed1 Bath850 SqFt
    1/23 23
    Active

    $350,000

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

    MLS# MDKE2006168

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 304 HADAWAY DR, Chestertown, MD 21620
    4 Beds2 Baths1,325 SqFt
    3D
    Price Dropped by $7K

    $314,900

    304 HADAWAY DR, Chestertown, MD 21620

    MLS# MDKE2006482

    Listed by Redfin Corporation

    Bright MLS (BMLS)
  • 117 WATER ST N #1B, Chestertown, MD 21620
    1 Bed1 Bath700 SqFt
    1/20 20
    Active

    $200,000

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

    MLS# MDKE2006164

    Listed by TTR Sotheby's International Realty

    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 2026. 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 2026. 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.