6,890

Chestertown, MD Homes

Section Image
  • 236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    236 Merganser Dr, Chestertown, MD 21620
    /14

    $85,000

    Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Current Estimated Value $158,393

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
    • 105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      105 S Water St, Chestertown, MD 21620
      /58

      Est $804,469

      Not Listed For Sale

      105 S Water St, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft
      • Built 1900
      105 S Water St, Chestertown, MD 21620

      Last Sold Summary

      • 64 Days On Market

  • 23741 L Rd, Chestertown, MD 21620
    23741 L Rd, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 1 Acre
    • $15,000 per Acre

    23741 L Rd, Chestertown, MD 21620

    Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all due diligence regarding perc testing, building suitability, zoning, utilities, and intended use.

    Taylor Leaverton Benson & Mangold, LLC

    23741 L Rd, Chestertown, MD 21620
  • 21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    21125 Iowa Ave, Chestertown, MD 21620
    /26

    $339,900

    Sold Jun 05, 2026

    21125 Iowa Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1962

    Last Sold Summary

    • $263/SF
    • 54 Days On Market

    Current Estimated Value $334,882

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21125 Iowa Ave, Chestertown, MD 21620
    • 114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      114 School Rd, Chestertown, MD 21620
      /39

      Est $256,693

      Not Listed For Sale

      114 School Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft
      • Built 1966
      114 School Rd, Chestertown, MD 21620

      Last Sold Summary

      • 71 Days On Market

  • 896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    896 Washington Ave, Chestertown, MD 21620
    /34

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    896 Washington Ave, Chestertown, MD 21620

    A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    896 Washington Ave, Chestertown, MD 21620
  • 10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    10121 Fairlee Rd, Chestertown, MD 21620
    /67

    $2,100,000

    Sold Feb 02, 2026

    10121 Fairlee Rd, Chestertown, MD 21620

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft
    • Built 1858

    Last Sold Summary

    • $424/SF
    • 58 Days On Market

    Current Estimated Value $2,132,111

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
    • 23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      23118 Raleigh Rd, Chestertown, MD 21620
      /36

      Est $397,189

      Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

  • 0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
    /2

    $38,000

    $23K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • 148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    148 E Step Rd, Chestertown, MD 21620
    /46

    $365,000

    Sold Apr 17, 2026

    148 E Step Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $261/SF
    • 16 Days On Market

    Current Estimated Value $363,510

    Last Listing Agent Norman Lee III Anne Arundel Properties, Inc.

    148 E Step Rd, Chestertown, MD 21620
    • 10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      10550 Klamath Rd, Chestertown, MD 21620
      /33

      Est $329,168

      Not Listed For Sale

      10550 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2006
      10550 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    9126 Fairlee Rd, Chestertown, MD 21620
    /20

    $344,000

    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620
  • 6 Byford Ct, Chestertown, MD 21620
    6 Byford Ct, Chestertown, MD 21620
    /2

    $749,500

    Sold Apr 13, 2026

    6 Byford Ct, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1978

    Last Sold Summary

    • $239/SF
    • 0 Days On Market

    Current Estimated Value $751,731

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6 Byford Ct, Chestertown, MD 21620
    • 116 Harlan Loop, Chestertown, MD 21620
      116 Harlan Loop, Chestertown, MD 21620
      116 Harlan Loop, Chestertown, MD 21620
      /28

      Est $532,851

      Not Listed For Sale

      116 Harlan Loop, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 4,067 Sq Ft
      • Built 2009
      116 Harlan Loop, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    206 Barroll Dr, Chestertown, MD 21620
    /35

    $438,000

    Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $441,809

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
    • 23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      23235 Myers Rd, Chestertown, MD 21620
      /7

      Est $322,697

      Not Listed For Sale

      23235 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23235 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

  • 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
    • 23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      23399 Cloquet Rd, Chestertown, MD 21620
      /13

      Est $337,807

      Not Listed For Sale

      23399 Cloquet Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2004
      23399 Cloquet Rd, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

  • 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 $1,112,619

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
    • 305 Washington Ave, Chestertown, MD 21620
      305 Washington Ave, Chestertown, MD 21620
      305 Washington Ave, Chestertown, MD 21620
      /28

      Est $564,102

      Not Listed For Sale

      305 Washington Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,476 Sq Ft
      • Built 1930
      305 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • 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 $322,348

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    105 Parma Rd, Chestertown, MD 21620
    • 101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      101 S College Ave, Chestertown, MD 21620
      /39

      Est $332,162

      Not Listed For Sale

      101 S College Ave, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft
      • Built 1920
      101 S College Ave, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 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 $483,785

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
    • 203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      203 Radcliffe Dr, Chestertown, MD 21620
      /12

      Est $349,459

      Not Listed For Sale

      203 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft
      • Built 1963
      203 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

  • 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
    • 316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      316 Roosevelt Dr, Chestertown, MD 21620
      /27

      Est $280,315

      Not Listed For Sale

      316 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1966
      316 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 37 Days On Market

  • 10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    /20

    $246,000

    Sold Aug 15, 2025

    10624 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $246/SF
    • 17 Days On Market

    Current Estimated Value $238,614

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
    • 508 Cannon St, Chestertown, MD 21620
      508 Cannon St, Chestertown, MD 21620
      508 Cannon St, Chestertown, MD 21620
      /20

      Est $297,353

      Not Listed For Sale

      508 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,240 Sq Ft
      • Built 1921
      508 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • 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 $659,854

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    • 21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      21286 Maine Ave, Chestertown, MD 21620
      /13

      Est $239,421

      Not Listed For Sale

      21286 Maine Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft
      • Built 2001
      21286 Maine Ave, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

  • 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
    • 545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      545 High St, Chestertown, MD 21620
      /28

      Est $273,283

      Not Listed For Sale

      545 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft
      • Built 1900
      545 High St, Chestertown, MD 21620

      Last Sold Summary

      • 46 Days On Market

  • 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 $694,229

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
    • 9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      9041 S Bayview Dr, Chestertown, MD 21620
      /47

      Est $331,581

      Not Listed For Sale

      9041 S Bayview Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft
      • Built 2009
      9041 S Bayview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

  • 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 $372,623

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling Rd, Chestertown, MD 21620
    • 10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      10640 Watonga Rd, Chestertown, MD 21620
      /31

      Est $305,044

      Not Listed For Sale

      10640 Watonga Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,196 Sq Ft
      • Built 1995
      10640 Watonga Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 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 $294,068

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    115 Acorn Dr, Chestertown, MD 21620
    • 217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      217 Radcliffe Dr, Chestertown, MD 21620
      /37

      Est $560,349

      Not Listed For Sale

      217 Radcliffe Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,467 Sq Ft
      • Built 2003
      217 Radcliffe Dr, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

  • 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

Showing Results 361 - 400, Page 10 of 18

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