6,868

Chestertown, MD Homes

Section Image
  • 201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    201 Boundary Ave, Chestertown, MD 21620
    /46

    $425,000 Sold Nov 17, 2025

    201 Boundary Ave, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1968

    Last Sold Summary

    • $137/SF
    • 59 Days On Market

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
    • 208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      /44

      Est $449,933 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,045 Sq Ft

      208 Byford Dr, Chestertown, MD 21620

      208 Byford Dr, Chestertown, MD 21620
  • 216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    216 Silver Heel Rd, Chestertown, MD 21620
    /32

    $360,000 Sold Jun 12, 2025

    216 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2022

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $362,191

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
    • 247 Devon Dr, Chestertown, MD 21620
      247 Devon Dr, Chestertown, MD 21620
      247 Devon Dr, Chestertown, MD 21620
      /24

      Est $507,740 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,316 Sq Ft

      247 Devon Dr, Chestertown, MD 21620

      247 Devon Dr, Chestertown, MD 21620
  • 209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    /63

    $535,000 Sold Mar 13, 2025

    209 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,328 Sq Ft
    • Built 1885

    Last Sold Summary

    • $230/SF
    • 10 Days On Market

    Current Estimated Value $600,997

    Last Listing Agent Andrea Alderdice Long & Foster Real Estate, Inc.

    209 N Queen St, Chestertown, MD 21620
    • 213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      /24

      Est $394,806 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft

      213 Devon Dr, Chestertown, MD 21620

      213 Devon Dr, Chestertown, MD 21620
  • 118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    118 Tuxedo Rd, Chestertown, MD 21620
    /26

    $235,000 Sold Aug 07, 2025

    118 Tuxedo Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 121 Days On Market

    Current Estimated Value $247,842

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
    • 8930 Orchard Dr, Chestertown, MD 21620
      8930 Orchard Dr, Chestertown, MD 21620
      8930 Orchard Dr, Chestertown, MD 21620
      /50

      Est $687,498 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,147 Sq Ft

      8930 Orchard Dr, Chestertown, MD 21620

      8930 Orchard Dr, Chestertown, MD 21620
  • 25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    /31

    $435,000 Sold Nov 03, 2025

    25800 Collins Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft
    • Built 1960

    Last Sold Summary

    • $201/SF
    • 22 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
    • 614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      /22

      Est $225,563 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      614 High St, Chestertown, MD 21620

      614 High St, Chestertown, MD 21620
  • 23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    /10

    $145,000 Sold Oct 14, 2025

    23065 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1957

    Last Sold Summary

    • $123/SF
    • 5 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    23065 Old Fairlee Rd, Chestertown, MD 21620
    • 612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      /21

      Est $209,756 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft

      612 High St, Chestertown, MD 21620

      612 High St, Chestertown, MD 21620
  • 101 Landing Ln Unit 39, Chestertown, MD 21620
    101 Landing Ln Unit 39, Chestertown, MD 21620
    101 Landing Ln Unit 39, Chestertown, MD 21620
    /35

    $600,000 Sold Jan 03, 2025

    101 Landing Ln Unit 39, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 3,300 Sq Ft
    • Built 2013

    Last Sold Summary

    • $182/SF
    • 151 Days On Market

    Current Estimated Value $656,408

    Last Listing Agent Sarah King Cross Street Realtors LLC

    101 Landing Ln Unit 39, Chestertown, MD 21620
    • 7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      /72

      Est $836,654 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft

      7996 Aldan Dr, Chestertown, MD 21620

      7996 Aldan Dr, Chestertown, MD 21620
  • 126 Metcalf Rd, Chestertown, MD 21620
    126 Metcalf Rd, Chestertown, MD 21620
    126 Metcalf Rd, Chestertown, MD 21620
    /25

    $230,000 Sold Nov 20, 2025

    126 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $202/SF
    • 21 Days On Market

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
    • 211 Manor Ave, Chestertown, MD 21620
      211 Manor Ave, Chestertown, MD 21620
      211 Manor Ave, Chestertown, MD 21620
      /22

      Est $283,554 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,388 Sq Ft

      211 Manor Ave, Chestertown, MD 21620

      211 Manor Ave, Chestertown, MD 21620
  • 10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    /20

    $525,000 Sold Oct 17, 2025

    10165 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,774 Sq Ft
    • Built 1987

    Last Sold Summary

    • $189/SF
    • 28 Days On Market

    Last Listing Agent Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
    • 8042 Brices Mill Rd, Chestertown, MD 21620
      8042 Brices Mill Rd, Chestertown, MD 21620
      8042 Brices Mill Rd, Chestertown, MD 21620
      /12

      Est $635,510 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft

      8042 Brices Mill Rd, Chestertown, MD 21620

      8042 Brices Mill Rd, Chestertown, MD 21620
  • 411 Fairview Dr, Chestertown, MD 21620
    411 Fairview Dr, Chestertown, MD 21620
    411 Fairview Dr, Chestertown, MD 21620
    /30

    $649,000 Sold Dec 20, 2024

    411 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1977

    Last Sold Summary

    • $386/SF
    • 27 Days On Market

    Current Estimated Value $650,632

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    411 Fairview Dr, Chestertown, MD 21620
    • 5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      /20

      Est $322,828 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      5772 Johnsontown Rd, Chestertown, MD 21620

      5772 Johnsontown Rd, Chestertown, MD 21620
  • 10578 Tonopah Rd, Chestertown, MD 21620
    10578 Tonopah Rd, Chestertown, MD 21620
    10578 Tonopah Rd, Chestertown, MD 21620
    /19

    $335,000 Sold Aug 08, 2025

    10578 Tonopah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $223/SF
    • 17 Days On Market

    Current Estimated Value $329,448

    Last Listing Agent David Moore Real Broker, LLC

    10578 Tonopah Rd, Chestertown, MD 21620
    • 10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      /17

      Est $282,299 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,237 Sq Ft

      10755 Glenola Rd, Chestertown, MD 21620

      10755 Glenola Rd, Chestertown, MD 21620
  • 201 Radcliffe Dr, Chestertown, MD 21620
    201 Radcliffe Dr, Chestertown, MD 21620
    201 Radcliffe Dr, Chestertown, MD 21620
    /36

    $795,000 Sold Nov 07, 2025

    201 Radcliffe Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,736 Sq Ft
    • Built 2011

    Last Sold Summary

    • $291/SF
    • 4 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
    • 8550 Caulks Field Rd, Chestertown, MD 21620
      8550 Caulks Field Rd, Chestertown, MD 21620
      8550 Caulks Field Rd, Chestertown, MD 21620
      /25

      Est $345,369 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      8550 Caulks Field Rd, Chestertown, MD 21620

      8550 Caulks Field Rd, Chestertown, MD 21620
  • 109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    /24

    $344,900 Sold Jun 25, 2025

    109 Edmore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1993

    Last Sold Summary

    • $257/SF
    • 24 Days On Market

    Current Estimated Value $342,495

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
    • 8049 Quaker Neck Rd, Chestertown, MD 21620
      8049 Quaker Neck Rd, Chestertown, MD 21620
      8049 Quaker Neck Rd, Chestertown, MD 21620
      /28

      Est $817,717 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,660 Sq Ft

      8049 Quaker Neck Rd, Chestertown, MD 21620

      8049 Quaker Neck Rd, Chestertown, MD 21620
  • 7775 Waterview Ln, Chestertown, MD 21620
    7775 Waterview Ln, Chestertown, MD 21620
    7775 Waterview Ln, Chestertown, MD 21620
    /37

    $625,000 Sold Jan 02, 2025

    7775 Waterview Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • Built 1937

    Last Sold Summary

    • $351/SF
    • 81 Days On Market

    Current Estimated Value $640,129

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7775 Waterview Ln, Chestertown, MD 21620
    • 626 High St, Chestertown, MD 21620
      626 High St, Chestertown, MD 21620
      626 High St, Chestertown, MD 21620
      /42

      Est $340,427 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,855 Sq Ft

      626 High St, Chestertown, MD 21620

      626 High St, Chestertown, MD 21620
  • 114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    /33

    $270,000 Sold Aug 25, 2025

    114 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1978

    Last Sold Summary

    • $256/SF
    • 72 Days On Market

    Current Estimated Value $271,831

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
    • 403 E Campus Ave, Chestertown, MD 21620
      403 E Campus Ave, Chestertown, MD 21620
      403 E Campus Ave, Chestertown, MD 21620
      /28

      Est $293,335 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      403 E Campus Ave, Chestertown, MD 21620

      403 E Campus Ave, Chestertown, MD 21620
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    /22

    $175,000 Sold Jul 25, 2025

    110 Philosophers Terrace, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $195/SF
    • 85 Days On Market

    Current Estimated Value $194,932

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
    • 10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      /27

      Est $300,745 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      10572 Klamath Rd, Chestertown, MD 21620

      10572 Klamath Rd, Chestertown, MD 21620
  • 21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    /16

    $195,000 Sold Apr 11, 2025

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1955

    Last Sold Summary

    • $144/SF
    • 0 Days On Market

    Current Estimated Value $199,205

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    • 219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      /8

      Est $445,924 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft

      219 Philosophers Terrace, Chestertown, MD 21620

      219 Philosophers Terrace, Chestertown, MD 21620
  • 206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    /36

    $375,000 Sold Aug 13, 2025

    206 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,302 Sq Ft
    • Built 2022

    Last Sold Summary

    • $163/SF
    • 1 Day On Market

    Last Listing Agent TJ Bennett Samson Properties

    206 Silver Heel Dr, Chestertown, MD 21620
    • 112 S Mill St, Chestertown, MD 21620
      112 S Mill St, Chestertown, MD 21620
      112 S Mill St, Chestertown, MD 21620
      /34

      Est $733,815 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft

      112 S Mill St, Chestertown, MD 21620

      112 S Mill St, Chestertown, MD 21620
  • 7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    /93

    $1,550,000 Sold Nov 07, 2025

    7961 Quaker Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft
    • Built 1952

    Last Sold Summary

    • $372/SF
    • 150 Days On Market

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
    • 209 Birch Run Rd, Chestertown, MD 21620
      209 Birch Run Rd, Chestertown, MD 21620
      209 Birch Run Rd, Chestertown, MD 21620
      /25

      Est $593,672 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,488 Sq Ft

      209 Birch Run Rd, Chestertown, MD 21620

      209 Birch Run Rd, Chestertown, MD 21620
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /77

    $4,221,800 Sold Nov 24, 2025

    23620 Lands End Rd, Chestertown, MD 21620

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft
    • Built 2001

    Last Sold Summary

    • $429/SF
    • 219 Days On Market

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
    • 203 Leeds Ct, Chestertown, MD 21620
      203 Leeds Ct, Chestertown, MD 21620
      203 Leeds Ct, Chestertown, MD 21620
      /41

      Est $471,028 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft

      203 Leeds Ct, Chestertown, MD 21620

      203 Leeds Ct, Chestertown, MD 21620

Showing Results 401 - 440, Page 11 of 18

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