Carelly Realty Group
  • Search
  • 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
104 Properties
Map

104 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
  • 7989 QUAKER NECK RD, Chestertown, MD 21620
    5 Beds5 Baths4,305 SqFt
    3D
    Active

    $2,750,000

    7989 QUAKER NECK RD, Chestertown, MD 21620

    MLS# MDKE2005590

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 10121 FAIRLEE RD, Chestertown, MD 21620
    6 Beds5 Baths4,954 SqFt
    1/67 67
    New

    $2,350,000

    10121 FAIRLEE RD, Chestertown, MD 21620

    MLS# MDKE2005852

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • LITTLE HARBOR WAY #1, Chestertown, MD 21620
    4 Beds4 Baths3,540 SqFt
    1/27 27
    Active

    $1,800,000

    LITTLE HARBOR WAY #1, Chestertown, MD 21620

    MLS# MDKE2004992

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 105 HIGH ST, Chestertown, MD 21620
    5 Beds5 Baths3,243 SqFt
    1/52 52
    Active

    $1,395,500

    105 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005002

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 120 SPEER RD, Chestertown, MD 21620
    1.21 Acres Lot
    1/9 9
    Active

    $1,250,000

    120 SPEER RD, Chestertown, MD 21620

    MLS# MDKE2005054

    Listed by Mackenzie Commercial R E SVCS, LLC

    Bright MLS (BMLS)
  • 329 HIGH ST, Chestertown, MD 21620
    3,996 Sqft Lot
    1/19 19
    Active

    $1,250,000

    329 HIGH ST, Chestertown, MD 21620

    MLS# MDKE2005172

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 300 HICKORY LN, Chestertown, MD 21620
    5 Beds4 Baths3,640 SqFt
    1/30 30
    Active

    $1,198,000

    300 HICKORY LN, Chestertown, MD 21620

    MLS# MDQA2013388

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 206 CANNON ST, Chestertown, MD 21620
    1.56 Acres
    1/9 9
    Active

    $1,150,000

    206 CANNON ST, Chestertown, MD 21620

    MLS# MDKE2003620

    Listed by Benson & Mangold, LLC

    Bright MLS (BMLS)
  • 492 PEAR TREE POINT RD, Chestertown, MD 21620
    3 Beds2 Baths3,720 SqFt
    1/73 73
    Active

    $920,000

    492 PEAR TREE POINT RD, Chestertown, MD 21620

    MLS# MDQA2015126

    Listed by Coldwell Banker Chesapeake Real Estate Company

    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)
  • 228 S WATER ST, Chestertown, MD 21620
    3 Beds4 Baths2,310 SqFt
    1/32 32
    Active

    $878,000

    228 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2005812

    Listed by Gunther-McClary Real Estate

    Bright MLS (BMLS)
  • 201 N LYNCHBURG ST, Chestertown, MD 21620
    4,342 Sqft Lot
    1/13 13
    Active

    $850,000

    201 N LYNCHBURG ST, Chestertown, MD 21620

    MLS# MDKE2005278

    Listed by RE/MAX Associates-Hockessin

    Bright MLS (BMLS)
  • 7844 CHESTER CT, Chestertown, MD 21620
    4 Beds3 Baths3,248 SqFt
    1/51 51
    Open 11/4 11AM-1PM

    $770,000

    7844 CHESTER CT, Chestertown, MD 21620

    MLS# MDKE2005796

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • JOHN CARVILL RD, Chestertown, MD 21620
    4 Beds3 Baths2,350 SqFt
    1/32 32
    New

    $750,000

    JOHN CARVILL RD, Chestertown, MD 21620

    MLS# MDKE2005716

    Listed by Shoreline Realty

    Bright MLS (BMLS)
  • 200 WASHINGTON AVE, Chestertown, MD 21620
    4 Beds4 Baths2,917 SqFt
    1/35 35
    Price Dropped by $50K

    $695,000

    200 WASHINGTON AVE, Chestertown, MD 21620

    MLS# MDKE2005538

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 118 LITTLE HARBOR WAY #201, Chestertown, MD 21620
    2 Beds3 Baths1,550 SqFt
    1/35 35
    Price Dropped by $20K

    $675,000

    118 LITTLE HARBOR WAY #201, Chestertown, MD 21620

    MLS# MDKE2005662

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 11040 KYLIE LN, Chestertown, MD 21620
    4 Beds4 Baths3,684 SqFt
    1/71 71
    Active

    $649,000

    11040 KYLIE LN, Chestertown, MD 21620

    MLS# MDKE2004586

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 206 S WATER ST, Chestertown, MD 21620
    4 Beds4 Baths2,008 SqFt
    1/43 43
    Active

    $619,000

    206 S WATER ST, Chestertown, MD 21620

    MLS# MDKE2005840

    Listed by TTR Sotheby's International Realty

    Bright MLS (BMLS)
  • 206 VALLEY, Chestertown, MD 21620
    4 Beds2 Baths2,869 SqFt
    1/35 35
    Price Dropped by $24K

    $615,000

    206 VALLEY, Chestertown, MD 21620

    MLS# MDKE2005762

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 251 DEVON DR, Chestertown, MD 21620
    3 Beds3 Baths3,935 SqFt
    1/54 54
    Active

    $595,000

    251 DEVON DR, Chestertown, MD 21620

    MLS# MDKE2005536

    Listed by Doug Ashley Realtors, LLC

    Bright MLS (BMLS)
  • 302 ROSIN DR, Chestertown, MD 21620
    5 Beds4 Baths3,877 SqFt
    1/70 70
    New

    $574,000

    302 ROSIN DR, Chestertown, MD 21620

    MLS# MDQA2015470

    Listed by Cross Street Realtors LLC

    Bright MLS (BMLS)
  • 103 LANDING LN, Chestertown, MD 21620
    2 Beds3 Baths2,100 SqFt
    1/69 69
    Active

    $559,000

    103 LANDING LN, Chestertown, MD 21620

    MLS# MDKE2005670

    Listed by Coldwell Banker Chesapeake Real Estate Company

    Bright MLS (BMLS)
  • 116 HARLAN LOOP, Chestertown, MD 21620
    5 Beds4 Baths4,067 SqFt
    1/21 21
    Price Dropped by $10K

    $519,000

    116 HARLAN LOOP, Chestertown, MD 21620

    MLS# MDKE2005610

    Listed by Samson Properties

    Bright MLS (BMLS)
  • 100 ADELA WAY, Chestertown, MD 21620
    4 Beds4 Baths3,799 SqFt
    1/71 71
    Active

    $515,000

    100 ADELA WAY, Chestertown, MD 21620

    MLS# MDKE2005636

    Listed by Berkshire Hathaway HomeServices PenFed Realty

    Bright MLS (BMLS)
  • 1
  • 2
  • 3
  • 4
  • 5

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 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.