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
33 Properties
Map

33 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
  • 25440 LEARMAN RD, Chestertown, MD 21620
    3 Beds4 Baths3,142 SqFt
    1/70 70
    Under Contract

    $3,000,000

    25440 LEARMAN RD, Chestertown, MD 21620

    MLS# MDKE2006468

    Listed by TTR Sotheby's International Realty

    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)
  • 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)
  • 205 RIVER RD, Chestertown, MD 21620
    4 Beds3 Baths2,877 SqFt
    1/68 68
    Pending

    $869,900

    205 RIVER RD, Chestertown, MD 21620

    MLS# MDQA2017560

    Listed by Clark & Co Realty, LLC

    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)
  • 7844 CHESTER CT, Chestertown, MD 21620
    4 Beds3 Baths3,248 SqFt
    1/51 51
    Under Contract

    $670,000

    7844 CHESTER CT, Chestertown, MD 21620

    MLS# MDKE2005796

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 204 DOUBLE CREEK RD, Chestertown, MD 21620
    3 Beds3 Baths2,927 SqFt
    1/46 46
    Price Dropped by $33K

    $565,000

    204 DOUBLE CREEK RD, Chestertown, MD 21620

    MLS# MDQA2015996

    Listed by Doug Ashley Realtors, LLC

    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)
  • 9816 FAIRLEE RD, Chestertown, MD 21620
    3 Beds3 Baths1,624 SqFt
    1/48 48
    Pending

    $535,000

    9816 FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2006488

    Listed by Long & Foster Real Estate, Inc.

    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)
  • 8620 PARK DR, Chestertown, MD 21620
    4 Beds3 Baths2,524 SqFt
    1/66 66
    Active

    $499,900

    8620 PARK DR, Chestertown, MD 21620

    MLS# MDKE2005850

    Listed by Doug Ashley Realtors, LLC

    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)
  • 25750 COLLINS AVE, Chestertown, MD 21620
    3 Beds2 Baths3,262 SqFt
    1/50 50
    Coming Soon

    $468,000

    25750 COLLINS AVE, Chestertown, MD 21620

    MLS# MDKE2006546

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 118 GRANT CT, Chestertown, MD 21620
    3 Beds2 Baths1,664 SqFt
    3D
    Under Contract

    $457,500

    118 GRANT CT, Chestertown, MD 21620

    MLS# MDQA2017356

    Listed by RE/MAX Executive

    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)
  • 704 TRUSLOW RD, Chestertown, MD 21620
    3 Beds3 Baths2,060 SqFt
    1/43 43
    Under Contract

    $440,000

    704 TRUSLOW RD, Chestertown, MD 21620

    MLS# MDQA2016632

    Listed by RE/MAX Executive

    Bright MLS (BMLS)
  • 215 FAIRVIEW DR, Chestertown, MD 21620
    3 Beds3 Baths1,784 SqFt
    1/57 57
    Under Contract

    $425,000

    215 FAIRVIEW DR, Chestertown, MD 21620

    MLS# MDQA2017090

    Listed by Long & Foster Real Estate, Inc.

    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)
  • 1
  • 2

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.