6,890

Chestertown, MD Homes

Section Image
  • 0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    /3

    $13,000

    Sold Mar 24, 2026

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    • Land
    • 3,920 Sq Ft
    • $144,444 per Acre

    Last Sold Summary

    • 699 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    • 502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      502 Cannon St, Chestertown, MD 21620
      /45

      Est $433,014

      Not Listed For Sale

      502 Cannon St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft
      • Built 1922
      502 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • 107 Longfellow Dr, Chestertown, MD 21620
    107 Longfellow Dr, Chestertown, MD 21620
    107 Longfellow Dr, Chestertown, MD 21620
    /37

    $278,500

    Sold May 14, 2026

    107 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • Built 1974

    Last Sold Summary

    • 6% Below List Price
    • 11 Days On Market

    Current Estimated Value $295,980

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow Dr, Chestertown, MD 21620
    • 111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      111 Manor Ave, Chestertown, MD 21620
      /44

      Est $423,801

      Not Listed For Sale

      111 Manor Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2007
      111 Manor Ave, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 200 Fey Rd, Chestertown, MD 21620
    200 Fey Rd, Chestertown, MD 21620
    200 Fey Rd, Chestertown, MD 21620
    /18

    $375,000

    Sold Oct 10, 2025

    200 Fey Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1996

    Last Sold Summary

    • $239/SF
    • 19 Days On Market

    Current Estimated Value $375,863

    Last Listing Agent Erik Hoferer Long & Foster Real Estate, Inc.

    200 Fey Rd, Chestertown, MD 21620
    • 631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      631 High St, Chestertown, MD 21620
      /9

      Est $234,779

      Not Listed For Sale

      631 High St, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,234 Sq Ft
      • Built 1917
      631 High St, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

  • 205 Pine St, Chestertown, MD 21620
    205 Pine St, Chestertown, MD 21620
    205 Pine St, Chestertown, MD 21620
    /23

    $296,337

    Sold Sep 30, 2025

    205 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft
    • Built 1955

    Last Sold Summary

    • $134/SF
    • 32 Days On Market

    Current Estimated Value $325,426

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, Chestertown, MD 21620
    • 207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      207 N Queen St, Chestertown, MD 21620
      /44

      Est $630,146

      Not Listed For Sale

      207 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft
      • Built 1900
      207 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 372 Days On Market

  • 10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    /49

    $960,000

    Sold Aug 27, 2025

    10715 Kasota Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • $282/SF
    • 5 Days On Market

    Current Estimated Value $1,027,735

    Last Listing Agent Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
    • 7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      7694 Waterview Ln, Chestertown, MD 21620
      /13

      Est $771,848

      Not Listed For Sale

      7694 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,322 Sq Ft
      • Built 1966
      7694 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

  • 9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, Chestertown, MD 21620
    9020 Georgetown Rd, Chestertown, MD 21620
    /10

    $65,000

    Sold Aug 11, 2025

    9020 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 2.36 Acres
    • $27,542 per Acre

    Last Sold Summary

    • 54 Days On Market

    Current Estimated Value $65,246

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
    • 10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      10705 Tilden Ln, Chestertown, MD 21620
      /50

      Est $1,325,337

      Not Listed For Sale

      10705 Tilden Ln, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,345 Sq Ft
      • Built 1943
      10705 Tilden Ln, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

  • 23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    /5

    $15,000

    Sold May 15, 2026

    23698 L Rd, Chestertown, MD 21620

    • Land
    • 2.6 Acres
    • $5,769 per Acre

    Last Sold Summary

    • 48% Below List Price
    • 127 Days On Market

    Current Estimated Value $137,500

    Last Listing Agent Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
    • 215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      /30

      Est $363,390

      Not Listed For Sale

      215 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1992
      215 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 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

    Current Estimated Value $432,330

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
    • 110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      /69

      Est $525,921

      Not Listed For Sale

      110 Camelot Dr, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft
      • Built 2007
      110 Camelot Dr, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • 318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    318 Lincoln Dr, Chestertown, MD 21620
    /21

    $255,000

    Sold Jan 16, 2026

    318 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1966

    Last Sold Summary

    • $266/SF
    • 58 Days On Market

    Current Estimated Value $257,067

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
    • 23315 Sandpiper Rd, Chestertown, MD 21620
      23315 Sandpiper Rd, Chestertown, MD 21620
      23315 Sandpiper Rd, Chestertown, MD 21620
      /37

      Est $299,041

      Not Listed For Sale

      23315 Sandpiper Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,272 Sq Ft
      • Built 1973
      23315 Sandpiper Rd, Chestertown, MD 21620

      Last Sold Summary

      • 120 Days On Market

  • 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 $243,966

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
    • 103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      /31

      Est $418,145

      Not Listed For Sale

      103 Trafford Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft
      • Built 2007
      103 Trafford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /73

    $850,000

    Sold Dec 19, 2025

    492 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 3,720 Sq Ft
    • Built 2001

    Last Sold Summary

    • $228/SF
    • 27 Days On Market

    Current Estimated Value $867,598

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
    • 503 N Kent St, Chestertown, MD 21620
      503 N Kent St, Chestertown, MD 21620
      503 N Kent St, Chestertown, MD 21620
      /26

      Est $365,967

      Not Listed For Sale

      503 N Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 1974
      503 N Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 79 Days On Market

  • 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

    Current Estimated Value $463,530

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
    • 202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      /34

      Est $400,022

      Not Listed For Sale

      202 Byford Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1965
      202 Byford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 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

    Current Estimated Value $163,466

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    23065 Old Fairlee Rd, Chestertown, MD 21620
    • 7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      /65

      Est $1,018,142

      Not Listed For Sale

      7755 Waterview Ln, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 4,730 Sq Ft
      • Built 2011
      7755 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 110 Days On Market

  • 100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    /21

    $215,000

    Sold Jul 21, 2026

    100 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft
    • Built 1953

    Last Sold Summary

    • $157/SF
    • 5 Days On Market

    Current Estimated Value $212,252

    Last Listing Agent David Moore Real Broker, LLC

    100 Prospect St, Chestertown, MD 21620
    • 7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      /22

      Est $501,503

      Not Listed For Sale

      7920 Carriage Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft
      • Built 1976
      7920 Carriage Ln, Chestertown, MD 21620

      Last Sold Summary

      • 21 Days On Market

  • 9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    /48

    $535,000

    Sold Jul 10, 2026

    9816 Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 1970

    Last Sold Summary

    • $329/SF
    • 13 Days On Market

    Current Estimated Value $528,792

    Last Listing Agent Scott Hogan Long & Foster Real Estate, Inc.

    9816 Fairlee Rd, Chestertown, MD 21620
    • 209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      209 E Campus Ave, Chestertown, MD 21620
      /34

      Est $440,480

      Not Listed For Sale

      209 E Campus Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft
      • Built 1947
      209 E Campus Ave, Chestertown, MD 21620

      Last Sold Summary

      • 145 Days On Market

  • 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

    Current Estimated Value $235,653

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
    • 9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      9545 Chantilly Farm Ln, Chestertown, MD 21620
      /64

      Est $1,483,000

      Not Listed For Sale

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 1986
      9545 Chantilly Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /68

    $855,000

    Sold Jun 24, 2026

    205 River Rd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $297/SF
    • 6 Days On Market

    Current Estimated Value $766,367

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    205 River Rd, Chestertown, MD 21620
    • 5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620
      /44

      Est $603,020

      Not Listed For Sale

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1890
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 26 Days On Market

  • 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

    Current Estimated Value $569,825

    Last Listing Agent Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
    • 8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      8500 Broad Neck Rd, Chestertown, MD 21620
      /25

      Est $494,506

      Not Listed For Sale

      8500 Broad Neck Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 2014
      8500 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 42 Days On Market

  • 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 $330,843

    Last Listing Agent David Moore Real Broker, LLC

    10578 Tonopah Rd, Chestertown, MD 21620
    • 208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      /44

      Est $404,152

      Not Listed For Sale

      208 Byford Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,045 Sq Ft
      • Built 1976
      208 Byford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

  • 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

    Current Estimated Value $784,361

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
    • 213 N Queen St, Chestertown, MD 21620
      213 N Queen St, Chestertown, MD 21620
      213 N Queen St, Chestertown, MD 21620
      /3

      Est $691,967

      Not Listed For Sale

      213 N Queen St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,945 Sq Ft
      • Built 1904
      213 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

Showing Results 401 - 440, Page 11 of 18

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