6,817

Chestertown, MD Homes

Section Image
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /21

    $160,000

    Sold Feb 13, 2026

    21316 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1955

    Last Sold Summary

    • $130/SF
    • 137 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21316 Persimmon Dr, Chestertown, MD 21620
    • 215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      215 Devon Dr, Chestertown, MD 21620
      /30

      Est $369,745

      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

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 231 Richard Dr, Chestertown, MD 21620
    231 Richard Dr, Chestertown, MD 21620
    /2

    $1,050,000

    Sold Jun 26, 2026

    231 Richard Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft
    • Built 1981

    Last Sold Summary

    • 18% Below List Price
    • $355/SF
    • 86 Days On Market

    Current Estimated Value $1,118,242

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
    • 110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      110 Camelot Dr, Chestertown, MD 21620
      /69

      Est $520,788

      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

      Last Listing Agent Chase Broadhurst RE/MAX Advantage Realty

  • 105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    105 Parma Rd, Chestertown, MD 21620
    /28

    $322,000

    Sold Nov 14, 2025

    105 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1992

    Last Sold Summary

    • $261/SF
    • 5 Days On Market

    Current Estimated Value $326,131

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    105 Parma Rd, Chestertown, MD 21620
    • 23315 Sandpiper Rd, Chestertown, MD 21620
      23315 Sandpiper Rd, Chestertown, MD 21620
      23315 Sandpiper Rd, Chestertown, MD 21620
      /37

      Est $304,826

      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

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $475,000

    Sold Dec 11, 2025

    101 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1979

    Last Sold Summary

    • $242/SF
    • 38 Days On Market

    Current Estimated Value $485,708

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
    • 103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      /31

      Est $401,161

      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

      Last Listing Agent Deric Beckett Berkshire Hathaway HomeServices PenFed Realty

  • 726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    726 Aldora Dr, Chestertown, MD 21620
    /35

    $485,960

    Sold Oct 31, 2025

    726 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $229/SF
    • 14 Days On Market

    Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

    726 Aldora Dr, 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 $371,453

      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

      Last Listing Agent Hugh Wyble Wyble Enterprises

  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /56

    $660,000

    Sold Jun 05, 2026

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 5% Below List Price
    • $412/SF
    • 83 Days On Market

    Current Estimated Value $661,490

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    • 202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      202 Byford Dr, Chestertown, MD 21620
      /34

      Est $408,139

      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

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 513 Round Top Rd, Chestertown, MD 21620
    513 Round Top Rd, Chestertown, MD 21620
    513 Round Top Rd, Chestertown, MD 21620
    /18

    $220,000

    Sold Apr 14, 2026

    513 Round Top Rd, Chestertown, MD 21620

    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $176/SF
    • 3 Days On Market

    Current Estimated Value $227,394

    Last Listing Agent Ben Garner Cummings & Co. Realtors

    513 Round Top Rd, Chestertown, MD 21620
    • 7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      7755 Waterview Ln, Chestertown, MD 21620
      /65

      Est $1,044,613

      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

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    /45

    $705,000

    Sold Sep 26, 2025

    9194 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1939

    Last Sold Summary

    • $483/SF
    • 19 Days On Market

    Current Estimated Value $709,069

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
    • 7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      7920 Carriage Ln, Chestertown, MD 21620
      /22

      Est $490,278

      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

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • 204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    204 Rolling Rd, Chestertown, MD 21620
    /31

    $340,000

    Sold Mar 19, 2026

    204 Rolling Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft
    • Built 1975

    Last Sold Summary

    • $148/SF
    • 56 Days On Market

    Current Estimated Value $360,776

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling 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 $429,515

      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

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • 115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    115 Acorn Dr, Chestertown, MD 21620
    /40

    $290,000

    Sold Jun 04, 2026

    115 Acorn Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,864 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 11 Days On Market

    Current Estimated Value $291,822

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    115 Acorn Dr, 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 $1,461,398

      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

      Last Listing Agent William Norris Select Land & Homes, LLC

  • 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
    • 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 $594,078

      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

      Last Listing Agent Christopher McClary Gunther-McClary Real Estate

  • 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 $298,110

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow Dr, 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 $496,097

      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

      Last Listing Agent Ginny Dauses Coldwell Banker Waterman Realty

  • 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 $381,125

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

    200 Fey Rd, Chestertown, MD 21620
    • 208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      208 Byford Dr, Chestertown, MD 21620
      /44

      Est $415,908

      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

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • 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 $326,344

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, 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 $656,338

      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

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • 202 Pine St, Chestertown, MD 21620
    202 Pine St, Chestertown, MD 21620
    /2

    $222,000

    Sold Sep 08, 2026

    202 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,341 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Above List Price
    • $166/SF
    • 7 Days On Market

    Current Estimated Value $276,943

    Last Listing Agent Jay McCall Coldwell Banker Chesapeake Real Estate Company

    202 Pine St, Chestertown, MD 21620
    • 213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      /24

      Est $398,885

      Not Listed For Sale

      213 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft
      • Built 2005
      213 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Christopher Buss Weichert Realtors - Blue Ribbon

  • 407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    407 High St, Chestertown, MD 21620
    /57

    $725,000

    Sold Sep 08, 2026

    407 High St, Chestertown, MD 21620

    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft
    • Built 1780

    Last Sold Summary

    • 12% Below List Price
    • $238/SF
    • 49 Days On Market

    Current Estimated Value $784,225

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
    • 7071 Pomona Rd, Chestertown, MD 21620
      7071 Pomona Rd, Chestertown, MD 21620
      7071 Pomona Rd, Chestertown, MD 21620
      /47

      Est $722,759

      Not Listed For Sale

      7071 Pomona Rd, Chestertown, MD 21620

      • 4 Beds
      • 4 Baths
      • 2,544 Sq Ft
      • Built 1991
      7071 Pomona Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 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 $95,000

    Last Listing Agent Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
    • 614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      /22

      Est $200,792

      Not Listed For Sale

      614 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1920
      614 High St, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • 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 $439,046

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
    • 612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      /21

      Est $196,619

      Not Listed For Sale

      612 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1920
      612 High St, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • 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 $256,814

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
    • 7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      /72

      Est $880,932

      Not Listed For Sale

      7996 Aldan Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft
      • Built 2001
      7996 Aldan Dr, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 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 $876,578

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
    • 7988 Aldan Dr, Chestertown, MD 21620
      7988 Aldan Dr, Chestertown, MD 21620
      7988 Aldan Dr, Chestertown, MD 21620
      /56

      Est $796,482

      Not Listed For Sale

      7988 Aldan Dr, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,394 Sq Ft
      • Built 2000
      7988 Aldan Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

Showing Results 401 - 440, Page 11 of 18

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