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119 Properties
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119 Properties Available In Chestertown

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MD >Chestertown >
Market Insights
  • CROMWELL CLARK RD, Chestertown, MD 21620
    87.34 Acres
    1/19 19
    Active

    $3,000,000

    CROMWELL CLARK RD, Chestertown, MD 21620

    MLS# MDKE2005156

    Listed by The Land Group

    Bright MLS (BMLS)
  • 7989 QUAKER NECK RD, Chestertown, MD 21620
    5 Beds5 Baths4,305 SqFt
    3D
    Open Sat 11AM-1PM

    $2,200,000

    7989 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 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)
  • 8796 MARYLAND PKWY, Chestertown, MD 21620
    9 Beds7 Baths4,776 SqFt
    1/60 60
    New

    $1,650,000

    8796 MARYLAND PKWY, Chestertown, MD 21620

    MLS# MDKE2006596

    Listed by Coldwell Banker Chesapeake Real Estate Company

    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)
  • 8276 BROAD NECK RD, Chestertown, MD 21620
    4 Beds4 Baths3,383 SqFt
    1/82 82
    Active

    $1,495,000

    8276 BROAD NECK RD, Chestertown, MD 21620

    MLS# MDKE2006216

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 104 MAPLE AVE, Chestertown, MD 21620
    10,540 Sqft Lot
    1/67 67
    Active

    $1,469,900

    104 MAPLE AVE, Chestertown, MD 21620

    MLS# MDKE2006386

    Listed by Real Broker, LLC - Annapolis

    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)
  • 22470 FAIRGALE FARM LN, Chestertown, MD 21620
    4 Beds5 Baths4,257 SqFt
    1/49 49
    Active

    $1,450,000

    22470 FAIRGALE FARM LN, Chestertown, MD 21620

    MLS# MDKE2006502

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 327 CANNON ST, Chestertown, MD 21620
    2,076 Sqft Lot
    1/39 39
    Active

    $1,300,000

    327 CANNON ST, Chestertown, MD 21620

    MLS# MDKE2006104

    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)
  • 202 ROYSTON SHORES RD, Chestertown, MD 21620
    4 Beds3 Baths2,292 SqFt
    1/72 72
    New

    $1,200,000

    202 ROYSTON SHORES RD, Chestertown, MD 21620

    MLS# MDQA2017462

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 25416 COMMERCE LN, Chestertown, MD 21620
    2.03 Acres Lot
    1/39 39
    New

    $1,100,000

    25416 COMMERCE LN, Chestertown, MD 21620

    MLS# MDKE2006664

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • #25 LANDING LN, Chestertown, MD 21620
    4 Beds4 Baths2,784 SqFt
    1/22 22
    Active

    $1,099,900

    #25 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005954

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 515 WASHINGTON AVE, Chestertown, MD 21620
    0.97 Acres Lot
    1/4 4
    Active

    $899,000

    515 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2000776

    Listed by EShore

    Bright MLS (BMLS)
  • 226 S WATER ST, Chestertown, MD 21620
    3 Beds4 Baths2,172 SqFt
    1/31 31
    Active

    $898,000

    226 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2006354

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 106 QUEEN ST S, Chestertown, MD 21620
    3 Beds4 Baths2,472 SqFt
    1/92 92
    Active

    $865,000

    106 QUEEN ST S, Chestertown, MD 21620

    MLS# MDKE2006152

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 104 LITTLE HARBOR WAY, Chestertown, MD 21620
    3 Beds3 Baths1,980 SqFt
    1/23 23
    Active

    $849,900

    104 LITTLE HARBOR WAY, Chestertown, MD 21620

    MLS# MDKE2005894

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 102 LITTLE HARBOR WAY, Chestertown, MD 21620
    3 Beds3 Baths1,964 SqFt
    1/23 23
    Active

    $839,500

    102 LITTLE HARBOR WAY, Chestertown, MD 21620

    MLS# MDKE2005950

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 104 LANDING LN, Chestertown, MD 21620
    3 Beds4 Baths2,192 SqFt
    1/24 24
    Active

    $813,900

    104 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005952

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 106 LANDING LN, Chestertown, MD 21620
    3 Beds4 Baths2,092 SqFt
    1/24 24
    Active

    $799,900

    106 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005892

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 407 HIGH ST, Chestertown, MD 21620
    3 Beds5 Baths3,047 SqFt
    1/57 57
    Price Dropped by $30K

    $798,000

    407 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006496

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • #35 LANDING LN, Chestertown, MD 21620
    3 Beds3 Baths1,964 SqFt
    1/26 26
    Active

    $786,900

    #35 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005956

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • #37 LANDING LN, Chestertown, MD 21620
    3 Beds3 Baths1,964 SqFt
    1/24 24
    Active

    $765,900

    #37 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005960

    Listed by Gunther-McClary Real Estate

    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

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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.