6,867

Chestertown, MD Homes

Section Image
    • 217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      /50

      Est $536,702 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,208 Sq Ft

      217 Birch Run Rd, Chestertown, MD 21620

      217 Birch Run Rd, Chestertown, MD 21620
  • 109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    /38

    $389,900 Sold Feb 06, 2025

    109 Grant Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2021

    Last Sold Summary

    • $290/SF
    • 40 Days On Market

    Current Estimated Value $395,582

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    109 Grant Ct, Chestertown, MD 21620
    • 7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      /15

      Est $252,414 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft

      7509 Sunburst Ave, Chestertown, MD 21620

      7509 Sunburst Ave, Chestertown, MD 21620
  • 125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    /48

    $350,000 Sold Dec 30, 2024

    125 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft
    • Built 1976

    Last Sold Summary

    • $167/SF
    • 50 Days On Market

    Current Estimated Value $358,677

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    125 Primrose Rd, Chestertown, MD 21620
    • 100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      /39

      Est $342,708 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft

      100 Malone Ave, Chestertown, MD 21620

      100 Malone Ave, Chestertown, MD 21620
  • 116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    /38

    $289,500 Sold May 05, 2025

    116 Oak Leaf Dr, Chestertown, MD 21620

    • 2 Beds
    • 4 Baths
    • 1,867 Sq Ft
    • Built 2004

    Last Sold Summary

    • $155/SF
    • 13 Days On Market

    Current Estimated Value $298,455

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
    • 22600 Fairgale Farm Ln, Chestertown, MD 21620
      22600 Fairgale Farm Ln, Chestertown, MD 21620
      22600 Fairgale Farm Ln, Chestertown, MD 21620
      /49

      Est $1,707,202 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,033 Sq Ft

      22600 Fairgale Farm Ln, Chestertown, MD 21620

      22600 Fairgale Farm Ln, Chestertown, MD 21620
  • 21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    /24

    $280,000 Sold Aug 07, 2025

    21363 Indiana Ave, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 10 Days On Market

    Current Estimated Value $274,766

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
    • 204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      /54

      Est $416,330 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft

      204 Richard Dr, Chestertown, MD 21620

      204 Richard Dr, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /60

    $725,000 Sold Aug 05, 2025

    24576 Langford Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft
    • Built 1989

    Last Sold Summary

    • $180/SF
    • 134 Days On Market

    Current Estimated Value $703,932

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
    • 115 N Queen St, Chestertown, MD 21620
      115 N Queen St, Chestertown, MD 21620
      115 N Queen St, Chestertown, MD 21620
      /62

      Est $699,850 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft

      115 N Queen St, Chestertown, MD 21620

      115 N Queen St, Chestertown, MD 21620
  • 0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    /2

    $75,000 Sold Sep 26, 2025

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620

    • Land
    • 1.49 Acres
    • $50,336 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    • 307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      /56

      Est $876,773 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,355 Sq Ft

      307 Washington Ave, Chestertown, MD 21620

      307 Washington Ave, Chestertown, MD 21620
  • 225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    /34

    $395,000 Sold Nov 10, 2025

    225 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2000

    Last Sold Summary

    • $214/SF
    • 16 Days On Market

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
    • 111 S Mill St, Chestertown, MD 21620
      111 S Mill St, Chestertown, MD 21620
      111 S Mill St, Chestertown, MD 21620
      /49

      Est $729,682 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 2,776 Sq Ft

      111 S Mill St, Chestertown, MD 21620

      111 S Mill St, Chestertown, MD 21620
  • 23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    /45

    $1,150,000 Sold Dec 10, 2025

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft
    • Built 1990

    Last Sold Summary

    • $259/SF
    • 361 Days On Market

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    • 24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      /24

      Est $369,836 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      24291 Chestertown Rd, Chestertown, MD 21620

      24291 Chestertown Rd, Chestertown, MD 21620
  • 21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    /31

    $191,000 Sold Oct 03, 2025

    21317 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft
    • Built 1955

    Last Sold Summary

    • $151/SF
    • 67 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
    • 425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      /18

      Est $671,901 Not Listed For Sale

      • Studio
      • 3,114 Sq Ft

      425 High St, Chestertown, MD 21620

      425 High St, Chestertown, MD 21620
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /22

    $490,000 Sold May 21, 2025

    101 S Mill St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft
    • Built 1900

    Last Sold Summary

    • $332/SF
    • 14 Days On Market

    Current Estimated Value $490,562

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • 100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      /41

      Est $465,857 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,000 Sq Ft

      100 Foxview Ct, Chestertown, MD 21620

      100 Foxview Ct, Chestertown, MD 21620
  • 10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    /49

    $905,000 Sold Nov 14, 2025

    10050 Forrest Ln, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1993

    Last Sold Summary

    • $497/SF
    • 4 Days On Market

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • 306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      /56

      Est $479,809 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft

      306 Mayfair Dr, Chestertown, MD 21620

      306 Mayfair Dr, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /2

    $119,500 Sold Jun 26, 2025

    205 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $118,317 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $123,526

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
    • 22954 Bay Shore Rd, Chestertown, MD 21620
      22954 Bay Shore Rd, Chestertown, MD 21620
      22954 Bay Shore Rd, Chestertown, MD 21620
      /73

      Est $255,704 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 2,336 Sq Ft

      22954 Bay Shore Rd, Chestertown, MD 21620

      22954 Bay Shore Rd, Chestertown, MD 21620
  • 106 Silver Heel Rd, Chestertown, MD 21620
    106 Silver Heel Rd, Chestertown, MD 21620
    106 Silver Heel Rd, Chestertown, MD 21620
    /43

    $355,000 Sold Jan 10, 2025

    106 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,672 Sq Ft
    • Built 2023

    Last Sold Summary

    • $212/SF
    • 0 Days On Market

    Current Estimated Value $365,820

    Last Listing Agent Chuck Zepp EXP Realty, LLC

    106 Silver Heel Rd, Chestertown, MD 21620
    • 8891 Georgetown Rd, Chestertown, MD 21620
      8891 Georgetown Rd, Chestertown, MD 21620
      8891 Georgetown Rd, Chestertown, MD 21620
      /32

      Est $295,721 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,600 Sq Ft

      8891 Georgetown Rd, Chestertown, MD 21620

      8891 Georgetown Rd, Chestertown, MD 21620
  • 10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    /47

    $872,500 Sold Nov 21, 2025

    10761 Kasota Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft
    • Built 2005

    Last Sold Summary

    • $338/SF
    • 32 Days On Market

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • 307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      /24

      Est $308,828 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft

      307 Cedar St, Chestertown, MD 21620

      307 Cedar St, Chestertown, MD 21620
  • 313 S Queen St, Chestertown, MD 21620
    313 S Queen St, Chestertown, MD 21620
    313 S Queen St, Chestertown, MD 21620
    /57

    $427,000 Sold Jan 29, 2025

    313 S Queen St, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 1,995 Sq Ft
    • Built 1997

    Last Sold Summary

    • $214/SF
    • 1 Day On Market

    Current Estimated Value $459,907

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    313 S Queen St, Chestertown, MD 21620
    • 109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      /54

      Est $464,237 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,428 Sq Ft

      109 Birch Run Rd, Chestertown, MD 21620

      109 Birch Run Rd, Chestertown, MD 21620
  • 130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    /25

    $431,000 Sold Apr 22, 2025

    130 Sheaffer Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • Built 1999

    Last Sold Summary

    • $244/SF
    • 1 Day On Market

    Current Estimated Value $440,025

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    130 Sheaffer Rd, Chestertown, MD 21620
    • 23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      /32

      Est $385,624 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft

      23530 Clarissa Rd, Chestertown, MD 21620

      23530 Clarissa Rd, Chestertown, MD 21620
  • 127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $355,000 Sold Oct 02, 2025

    127 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1963

    Last Sold Summary

    • $427/SF
    • 10 Days On Market

    Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

    127 Char Nor Manor Blvd, Chestertown, MD 21620
    • 24581 Willow Oak Ln, Chestertown, MD 21620
      24581 Willow Oak Ln, Chestertown, MD 21620
      24581 Willow Oak Ln, Chestertown, MD 21620
      /5

      Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft

      24581 Willow Oak Ln, Chestertown, MD 21620

      24581 Willow Oak Ln, Chestertown, MD 21620
  • 103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    /90

    $585,000 Sold Nov 13, 2025

    103 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft
    • Built 2008

    Last Sold Summary

    • $105/SF
    • 54 Days On Market

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • 27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      /45

      Est $540,932 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,824 Sq Ft

      27325 Preston Ln, Chestertown, MD 21620

      27325 Preston Ln, Chestertown, MD 21620
  • 10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    /29

    $296,500 Sold Jul 25, 2025

    10670 Tintah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1999

    Last Sold Summary

    • $211/SF
    • 11 Days On Market

    Current Estimated Value $297,694

    Last Listing Agent Bronwyn Scott Samson Properties

    10670 Tintah Rd, Chestertown, MD 21620
    • 8489 Broad Neck Rd, Chestertown, MD 21620
      8489 Broad Neck Rd, Chestertown, MD 21620
      8489 Broad Neck Rd, Chestertown, MD 21620
      /25

      Est $317,156 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft

      8489 Broad Neck Rd, Chestertown, MD 21620

      8489 Broad Neck Rd, Chestertown, MD 21620
  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /23

    $290,000 Sold Aug 13, 2025

    107 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 2005

    Last Sold Summary

    • $210/SF
    • 234 Days On Market

    Current Estimated Value $307,597

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620

Showing Results 441 - 480, Page 12 of 18

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