Carelly Realty Group
  • 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
  • Register
  • Sign In

All Property Listings

Filters Reset
1 Filter
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
Beds
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Baths
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Reset
1 Filter
1 Filter Applied

Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
Beds
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Baths
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Days On Site
Advanced
Less Than
Days
Unit Level

SqFt
Switch to Acre
Sqft
Sqft
Lot Size
Switch to Acre
Sqft
Sqft
Price per Sqft
Monthly HOA Fee
Year Built
Stories
Kitchens
Acres
Full Bathrooms
Half Bathrooms
Frontage
Tax Amount
Land Lease Fee
Keyword
Maintenance Fee
Assessed Value

Fireplace Number

Parking Space
Garage Space
Carport Spaces

Open House
Has Picture
New
Hot
Virtual Tour
3D Tour
Price Reduced
Save Search (2)
Save your search to get Alerts
19 Properties
Map

19 Properties Available In Chestertown

  • Price-High To Low
  • Default
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
MD >Chestertown >
Market Insights
  • 201 N LYNCHBURG ST, Chestertown, MD 21620
    4,342 Sqft Lot
    1/13 13
    Price Dropped by $45K

    $750,000

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2006082

    Listed by RE/MAX Associates-Hockessin

    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)
  • 24295 LANGFORD RD, Chestertown, MD 21620
    2 Beds3 Baths1,857 SqFt
    1/71 71
    Under Contract

    $430,000

    24295 LANGFORD RD, Chestertown, MD 21620

    MLS# MDKE2006320

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 222 MOUNT VERNON AVE, Chestertown, MD 21620
    4 Beds2 Baths1,656 SqFt
    1/29 29
    Price Dropped by $5K

    $429,999

    222 MOUNT VERNON AVE, Chestertown, MD 21620

    MLS# MDKE2005876

    Listed by Long & Foster Real Estate, Inc.

    Bright MLS (BMLS)
  • 522 HIGH ST, Chestertown, MD 21620
    2 Beds3 Baths1,518 SqFt
    1/15 15
    Price Dropped by $25K

    $425,000

    522 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2006614

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • 103 TRAFFORD DR, Chestertown, MD 21620
    3 Beds3 Baths1,944 SqFt
    1/65 65
    Open Sat 11AM-1PM

    $399,900

    103 TRAFFORD DR, Chestertown, MD 21620

    MLS# MDKE2006416

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 240 MERGANSER DR, Chestertown, MD 21620
    3 Beds2 Baths1,120 SqFt
    3D
    Price Dropped by $10K

    $389,000

    240 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2016900

    Listed by Chesapeake Real Estate Associates, LLC

    Bright MLS (BMLS)
  • 107 FLYING CLOUD DR, Chestertown, MD 21620
    5 Beds4 Baths2,534 SqFt
    1/51 51
    Price Dropped by $10K

    $385,000

    107 FLYING CLOUD DR, Chestertown, MD 21620

    MLS# MDKE2006510

    Listed by CENTURY 21 New Millennium

    Bright MLS (BMLS)
  • 214 SILVER HEEL RD, Chestertown, MD 21620
    4 Beds3 Baths1,972 SqFt
    1/26 26
    Price Dropped by $10K

    $340,000

    214 SILVER HEEL RD, Chestertown, MD 21620

    MLS# MDKE2006498

    Listed by Cross Street Realtors LLC

    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)
  • 21217 TEXAS AVE, Chestertown, MD 21620
    2 Beds1 Bath912 SqFt
    1/20 20
    Price Dropped by $20K

    $244,500

    21217 TEXAS AVE, Chestertown, MD 21620

    MLS# MDKE2006364

    Listed by RE/MAX Leading Edge

    Bright MLS (BMLS)
  • 144 PROSPECT ST, Chestertown, MD 21620
    2 Beds2 Baths1,082 SqFt
    1/18 18
    Under Contract

    $159,000

    144 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006494

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 110 PROSPECT ST, Chestertown, MD 21620
    3 Beds2 Baths2,210 SqFt
    1/6 6
    New

    $119,895

    110 PROSPECT ST, Chestertown, MD 21620

    MLS# MDKE2006626

    Listed by ANR Realty, LLC

    Bright MLS (BMLS)
  • 234 N COLLEGE AVE, Chestertown, MD 21620
    2 Beds1 Bath1,296 SqFt
    1/3 3
    Price Dropped by $20K

    $100,000

    234 N COLLEGE AVE, Chestertown, MD 21620

    MLS# MDKE2006670

    Listed by Cummings & Co Realtors

    Bright MLS (BMLS)
  • 8886 GEORGETOWN RD, Chestertown, MD 21620
    4.03 Acres
    1/3 3
    Price Dropped by $5K

    $80,000

    8886 GEORGETOWN RD, Chestertown, MD 21620

    MLS# MDKE2006634

    Listed by Samson Properties

    Bright MLS (BMLS)
  • 228 MERGANSER DR, Chestertown, MD 21620
    0.51 Acres
    1/13 13
    Price Dropped by $24K

    $75,000

    228 MERGANSER DR, Chestertown, MD 21620

    MLS# MDQA2017240

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • JOHNSONTOWN RD, Chestertown, MD 21620
    0.9 Acres
    1/16 16
    Price Dropped by $10K

    $25,000

    JOHNSONTOWN RD, Chestertown, MD 21620

    MLS# MDKE2005550

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
  • 1010 TWIN CT, Chestertown, MD 21620
    4 Beds2 Baths1,476 SqFt
    1/14 14
    Active

    $2,400

    1010 TWIN CT, Chestertown, MD 21620

    MLS# MDKE2006610

    Listed by Kevin Dey Realty

    Bright MLS (BMLS)
  • 7501 CHURCH HILL RD #5, Chestertown, MD 21620
    2 Beds1 Bath1,000 SqFt
    1/17 17
    Active

    $1,800

    7501 CHURCH HILL RD #5, Chestertown, MD 21620

    MLS# MDQA2016372

    Listed by Brenton Realty Group

    Bright MLS (BMLS)
  • 1

explore listings in Chestertown

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
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.
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.