6,817

Chestertown, MD Homes

Section Image
    • 7121 Quaker Neck Rd, Chestertown, MD 21620
      7121 Quaker Neck Rd, Chestertown, MD 21620
      7121 Quaker Neck Rd, Chestertown, MD 21620
      /22

      Est $127,038

      Not Listed For Sale

      7121 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 930 Sq Ft
      • Built 1959
      7121 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    • 529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      /30

      Est $404,045

      Not Listed For Sale

      529 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1900
      529 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    • 813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      /35

      Est $419,783

      Not Listed For Sale

      813 S Meadowview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,509 Sq Ft
      • Built 2002
      813 S Meadowview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    • 703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      /31

      Est $229,768

      Not Listed For Sale

      703 High St, Chestertown, MD 21620

      • 4 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1951
      703 High St, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kristie Midash L. C. Parker Real Estate

    • 1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      /50

      Est $374,584

      Not Listed For Sale

      1006 Twin Ct, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1989
      1006 Twin Ct, Chestertown, MD 21620

      Last Sold Summary

      • 96 Days On Market

      Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    • 21363 Indiana Ave, Chestertown, MD 21620
      21363 Indiana Ave, Chestertown, MD 21620
      21363 Indiana Ave, Chestertown, MD 21620
      /24

      Est $272,500

      Not Listed For Sale

      21363 Indiana Ave, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 896 Sq Ft
      • Built 1955
      21363 Indiana Ave, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    • 211 David Dr, Chestertown, MD 21620
      211 David Dr, Chestertown, MD 21620
      211 David Dr, Chestertown, MD 21620
      /52

      Est $811,275

      Not Listed For Sale

      211 David Dr, Chestertown, MD 21620

      • 4 Beds
      • 4 Baths
      • 4,401 Sq Ft
      • Built 1963
      211 David Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    • 23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      /41

      Est $391,317

      Not Listed For Sale

      23120 Club Terrace, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,789 Sq Ft
      • Built 1969
      23120 Club Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    • 25285 Foxchase Dr, Chestertown, MD 21620
      25285 Foxchase Dr, Chestertown, MD 21620
      25285 Foxchase Dr, Chestertown, MD 21620
      /39

      Est $576,378

      Not Listed For Sale

      25285 Foxchase Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,010 Sq Ft
      • Built 1992
      25285 Foxchase Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    • 9020 Cumberland St, Chestertown, MD 21620
      9020 Cumberland St, Chestertown, MD 21620
      9020 Cumberland St, Chestertown, MD 21620
      /48

      Est $255,126

      Not Listed For Sale

      9020 Cumberland St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 1949
      9020 Cumberland St, Chestertown, MD 21620

      Last Sold Summary

      • 263 Days On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • 9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      /57

      Est $750,214

      Not Listed For Sale

      9762 Vogeler Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,521 Sq Ft
      • Built 1900
      9762 Vogeler Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Tammy Studebaker EXP Realty, LLC

    • 10589 Klamath Rd, Chestertown, MD 21620
      10589 Klamath Rd, Chestertown, MD 21620
      10589 Klamath Rd, Chestertown, MD 21620
      /33

      Est $318,039

      Not Listed For Sale

      10589 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft
      • Built 1994
      10589 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

    • 8220 Airy Hill Rd, Chestertown, MD 21620
      8220 Airy Hill Rd, Chestertown, MD 21620
      8220 Airy Hill Rd, Chestertown, MD 21620
      /20

      Est $264,000

      Not Listed For Sale

      8220 Airy Hill Rd, Chestertown, MD 21620

      • Built 1920
      8220 Airy Hill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Sarah King Cross Street Realtors LLC

    • 308 Landing Ln, Chestertown, MD 21620
      308 Landing Ln, Chestertown, MD 21620
      308 Landing Ln, Chestertown, MD 21620
      /32

      Est $799,243

      Not Listed For Sale

      308 Landing Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,204 Sq Ft
      • Built 2017
      308 Landing Ln, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent John Burke Gunther-McClary Real Estate

    • 24576 Langford Rd, Chestertown, MD 21620
      24576 Langford Rd, Chestertown, MD 21620
      24576 Langford Rd, Chestertown, MD 21620
      /60

      Est $718,435

      Not Listed For Sale

      24576 Langford Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 4,023 Sq Ft
      • Built 1989
      24576 Langford Rd, Chestertown, MD 21620

      Last Sold Summary

      • 134 Days On Market

      Last Listing Agent Nancy McGuire Maryland Heritage Properties

    • 7671 Waterview Ln, Chestertown, MD 21620
      7671 Waterview Ln, Chestertown, MD 21620
      7671 Waterview Ln, Chestertown, MD 21620
      /13

      Est $419,325

      Not Listed For Sale

      7671 Waterview Ln, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 2,153 Sq Ft
      • Built 1952
      7671 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Aaron Butler Real Estate Consultants

    • 7500 Shortall St, Chestertown, MD 21620
      7500 Shortall St, Chestertown, MD 21620
      7500 Shortall St, Chestertown, MD 21620
      /24

      Est $309,681

      Not Listed For Sale

      7500 Shortall St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 2018
      7500 Shortall St, Chestertown, MD 21620

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Lona Todd Taylor Properties

    • 7519 Quaker Neck Rd, Chestertown, MD 21620
      7519 Quaker Neck Rd, Chestertown, MD 21620
      7519 Quaker Neck Rd, Chestertown, MD 21620
      /19

      Est $253,702

      Not Listed For Sale

      7519 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,136 Sq Ft
      • Built 1956
      7519 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lori Sample RE/MAX Chesapeake

    • 7413 Poplar Ave, Chestertown, MD 21620
      7413 Poplar Ave, Chestertown, MD 21620
      7413 Poplar Ave, Chestertown, MD 21620
      /11

      Est $170,467

      Not Listed For Sale

      7413 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1962
      7413 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • 6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      /73

      Est $544,777

      Not Listed For Sale

      6270 Quaker Neck Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 2011
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    • 7775 Waterview Ln, Chestertown, MD 21620
      7775 Waterview Ln, Chestertown, MD 21620
      7775 Waterview Ln, Chestertown, MD 21620
      /37

      Est $593,764

      Not Listed For Sale

      7775 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 1937
      7775 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • 6292 Broad Neck Rd, Chestertown, MD 21620
      6292 Broad Neck Rd, Chestertown, MD 21620
      6292 Broad Neck Rd, Chestertown, MD 21620
      /19

      Est $220,180

      Not Listed For Sale

      6292 Broad Neck Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,150 Sq Ft
      • Built 1900
      6292 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    • 22939 Bay Shore Rd, Chestertown, MD 21620
      22939 Bay Shore Rd, Chestertown, MD 21620
      22939 Bay Shore Rd, Chestertown, MD 21620
      /32

      Est $334,311

      Not Listed For Sale

      22939 Bay Shore Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,505 Sq Ft
      • Built 1999
      22939 Bay Shore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    • 22956 Fairgale Farm Ln, Chestertown, MD 21620
      22956 Fairgale Farm Ln, Chestertown, MD 21620
      22956 Fairgale Farm Ln, Chestertown, MD 21620
      /82

      Est $1,326,358

      Not Listed For Sale

      22956 Fairgale Farm Ln, Chestertown, MD 21620

      • 5 Beds
      • 4.5 Baths
      • 6,459 Sq Ft
      • Built 2000
      22956 Fairgale Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    • 23055 Parsons Rd, Chestertown, MD 21620
      23055 Parsons Rd, Chestertown, MD 21620
      23055 Parsons Rd, Chestertown, MD 21620
      /33

      Est $330,055

      Not Listed For Sale

      23055 Parsons Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,473 Sq Ft
      • Built 1965
      23055 Parsons Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Sharon Clark Clark & Co Realty, LLC

    • 24349 Chestertown Rd, Chestertown, MD 21620
      24349 Chestertown Rd, Chestertown, MD 21620
      24349 Chestertown Rd, Chestertown, MD 21620
      /32

      Est $331,973

      Not Listed For Sale

      24349 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,327 Sq Ft
      • Built 1962
      24349 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    • 8842 Fairlee Rd, Chestertown, MD 21620
      8842 Fairlee Rd, Chestertown, MD 21620
      8842 Fairlee Rd, Chestertown, MD 21620
      /13

      Est $228,554

      Not Listed For Sale

      8842 Fairlee Rd, Chestertown, MD 21620

      • Built 1960
      8842 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    • 23060 Old Fairlee Rd, Chestertown, MD 21620
      23060 Old Fairlee Rd, Chestertown, MD 21620
      23060 Old Fairlee Rd, Chestertown, MD 21620
      /7

      Est $116,851

      Not Listed For Sale

      23060 Old Fairlee Rd, Chestertown, MD 21620

      • Studio
      • 1,040 Sq Ft
      • Built 1900
      23060 Old Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 210 Days On Market

      Last Listing Agent Julia Hilfiker Gunther-McClary Real Estate

    • 9050 Point Ln, Chestertown, MD 21620
      9050 Point Ln, Chestertown, MD 21620
      9050 Point Ln, Chestertown, MD 21620
      /71

      Est $782,703

      Not Listed For Sale

      9050 Point Ln, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 3,166 Sq Ft
      • Built 2000
      9050 Point Ln, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    • 9096 Fairlee Rd, Chestertown, MD 21620
      9096 Fairlee Rd, Chestertown, MD 21620
      9096 Fairlee Rd, Chestertown, MD 21620
      /23

      Est $266,242

      Not Listed For Sale

      9096 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1900
      9096 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • 8899 Georgetown Rd, Chestertown, MD 21620
      8899 Georgetown Rd, Chestertown, MD 21620
      8899 Georgetown Rd, Chestertown, MD 21620
      /17

      Est $248,209

      Not Listed For Sale

      8899 Georgetown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 966 Sq Ft
      • Built 1968
      8899 Georgetown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • 22532 Tolchester Beach Rd, Chestertown, MD 21620
      22532 Tolchester Beach Rd, Chestertown, MD 21620
      22532 Tolchester Beach Rd, Chestertown, MD 21620
      /8

      Not Listed For Sale

      22532 Tolchester Beach Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,696 Sq Ft
      • Built 1920
      22532 Tolchester Beach Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Matthew Altizer ANR Realty, LLC

    • 10630 Club Rd, Chestertown, MD 21620
      10630 Club Rd, Chestertown, MD 21620
      10630 Club Rd, Chestertown, MD 21620
      /28

      Est $364,375

      Not Listed For Sale

      10630 Club Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1963
      10630 Club Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

    • 8970 Cumberland St, Chestertown, MD 21620
      8970 Cumberland St, Chestertown, MD 21620
      8970 Cumberland St, Chestertown, MD 21620
      /44

      Est $251,738

      Not Listed For Sale

      8970 Cumberland St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1945
      8970 Cumberland St, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jonathan Scheffenacker Redfin Corp

    • 21199 Iowa Ave, Chestertown, MD 21620
      21199 Iowa Ave, Chestertown, MD 21620
      21199 Iowa Ave, Chestertown, MD 21620
      /29

      Est $323,688

      Not Listed For Sale

      21199 Iowa Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 2003
      21199 Iowa Ave, Chestertown, MD 21620

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Thomas Huston Real Broker LLC

    • 8858 Georgetown Rd, Chestertown, MD 21620
      8858 Georgetown Rd, Chestertown, MD 21620
      8858 Georgetown Rd, Chestertown, MD 21620
      /15

      Est $335,901

      Not Listed For Sale

      8858 Georgetown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 2024
      8858 Georgetown Rd, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Andy Batch Keller Williams Select Realtors of Annapolis

    • 22153 1st Point Rd, Chestertown, MD 21620
      22153 1st Point Rd, Chestertown, MD 21620
      22153 1st Point Rd, Chestertown, MD 21620
      /87

      Est $1,097,133

      Not Listed For Sale

      22153 1st Point Rd, Chestertown, MD 21620

      • 5 Beds
      • 6 Baths
      • 3,078 Sq Ft
      • Built 1975
      22153 1st Point Rd, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    • 23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      /34

      Est $169,724

      Not Listed For Sale

      23087 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 808 Sq Ft
      • Built 1964
      23087 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Amy Occorso Real Estate Professionals, Inc.

    • 9220 N Bayview Ave, Chestertown, MD 21620
      9220 N Bayview Ave, Chestertown, MD 21620
      9220 N Bayview Ave, Chestertown, MD 21620
      /22

      Est $1,246,438

      Not Listed For Sale

      9220 N Bayview Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,028 Sq Ft
      • Built 1993
      9220 N Bayview Ave, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

    • 24105 Chestertown Rd, Chestertown, MD 21620
      24105 Chestertown Rd, Chestertown, MD 21620
      24105 Chestertown Rd, Chestertown, MD 21620
      /17

      Est $289,354

      Not Listed For Sale

      24105 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,317 Sq Ft
      • Built 1970
      24105 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

Showing Results 561 - 600, Page 15 of 18

Maryland Kent County

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group