6,886

Chestertown, MD Homes

Section Image
  • /22

    $155,200 Sold Mar 31, 2025

    Lot 4 Muirfield Dr, Chestertown, MD 21620

    • Land
    • 1.9 Acres
    • $81,684 per Acre

    Last Sold Summary

    • 300 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    Lot 4 Muirfield Dr, Chestertown, MD 21620
    • /13

      Est $347,774 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

      • 16% Above List Price
      • $198/SF
      • 41 Days On Market

      Last Sold Price $300,000

      Last Listing Agent David Moore Real Broker, LLC

  • /54

    $249,500

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    112 Metcalf Rd, Chestertown, MD 21620

    This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking

    April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
  • /30

    $1,100,000 Sold Jan 16, 2026

    300 Hickory Ln, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 1940

    Last Sold Summary

    • $302/SF
    • 163 Days On Market

    Current Estimated Value $1,146,131

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
    • /39

      Est $329,368 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

      • 8% Above List Price
      • $295/SF
      • 1 Day On Market

      Last Sold Price $305,435

      Last Listing Agent Jimmy White Long & Foster

  • /8

    $89,500

    • Land
    • 3.92 Acres
    • $22,832 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated palustrine forested shrub wetlands, though

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • /43

    $379,900 Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $397,238

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
    • /12

      Est $365,553 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

      • 59% Above List Price
      • $131/SF
      • 12 Days On Market

      Last Sold Price $230,111

      Last Listing Agent Alex Modaressi RE/MAX

  • /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
  • /71

    $745,000 Sold Jun 26, 2025

    9050 Point Ln, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,166 Sq Ft
    • Built 2000

    Last Sold Summary

    • $235/SF
    • 7 Days On Market

    Current Estimated Value $781,571

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    9050 Point Ln, Chestertown, MD 21620
    • /27

      Est $288,449 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

      • 3% Above List Price
      • $233/SF
      • 37 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /2

    $38,000

    • Land
    • 0.34 Acre
    • $111,765 per Acre

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Redfield Rd Unit MDKE2002842, Chestertown, MD 21620
  • /25

    $385,000 Sold Apr 11, 2025

    149 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft
    • Built 1982

    Last Sold Summary

    • $213/SF
    • 19 Days On Market

    Current Estimated Value $395,710

    Last Listing Agent Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
    • /13

      Est $250,427 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

      • 16% Above List Price
      • $215/SF
      • 83 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Kristie Midash L. C. Parker Real Estate

  • /22

    $350,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft

    121 Primrose Rd, Chestertown, MD 21620

    Motivated Seller. Welcome to 121 Primrose Road, a well-built two-story home offering 2,034 square feet of living space on a .345-acre lot, located just outside downtown Chestertown in a quiet setting. The upper level includes three bedrooms and two full bathrooms, while the main level offers a convenient half bath. The first floor features a bright living area, a traditional dining space, and a

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose Rd, Chestertown, MD 21620
  • /32

    $782,500 Sold May 09, 2025

    308 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2017

    Last Sold Summary

    • $355/SF
    • 10 Days On Market

    Current Estimated Value $811,681

    Last Listing Agent John Burke Gunther-McClary Real Estate

    308 Landing Ln, Chestertown, MD 21620
    • /28

      Est $301,945 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

      • 21% Above List Price
      • $269/SF
      • 46 Days On Market

      Last Sold Price $249,900

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • /29

    $264,900 Sold Oct 30, 2025

    24415 Chestertown Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,110 Sq Ft
    • Built 1962

    Last Sold Summary

    • $239/SF
    • 23 Days On Market

    Current Estimated Value $263,934

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    24415 Chestertown Rd, Chestertown, MD 21620
    • /47

      Est $331,504 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

      • 11% Above List Price
      • $221/SF
      • 45 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Gregory Osborn Long & Foster

  • /22

    $319,000 Sold Mar 31, 2025

    201 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1985

    Last Sold Summary

    • $269/SF
    • 49 Days On Market

    Current Estimated Value $327,369

    Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
    • /69

      Est $1,394,906 Not Listed For Sale

      10069 John Carvill Rd, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft
      • Built 1978
      10069 John Carvill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $436/SF
      • 5 Days On Market

      Last Sold Price $1,250,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /30

    $400,000 Sold Mar 12, 2025

    204 Pine Cove Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft
    • Built 2021

    Last Sold Summary

    • $185/SF
    • 19 Days On Market

    Current Estimated Value $412,608

    Last Listing Agent Kelly Harris Coldwell Banker Realty

    204 Pine Cove Ln, Chestertown, MD 21620
    • /37

      Est $596,147 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% Above List Price
      • $385/SF
      • 6 Days On Market

      Last Sold Price $564,500

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /39

    $355,000 Sold Mar 31, 2025

    105 Justin Buch Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1991

    Last Sold Summary

    • $296/SF
    • 19 Days On Market

    Current Estimated Value $354,375

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
    • /45

      Est $478,058 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

      • 19% Above List Price
      • $275/SF
      • 7 Days On Market

      Last Sold Price $402,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /70

    $550,000 Sold Dec 05, 2025

    302 Rosin Dr, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 3,877 Sq Ft
    • Built 1996

    Last Sold Summary

    • $142/SF
    • 5 Days On Market

    Current Estimated Value $555,174

    Last Listing Agent Lori Willis Century 21 Gold Key Realty

    302 Rosin Dr, Chestertown, MD 21620
    • /44

      Est $426,238 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

      • 9% Above List Price
      • $229/SF
      • 3 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /48

    $535,000 Sold Nov 05, 2025

    5179 Quaker Neck Rd, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1890

    Last Sold Summary

    • $466/SF
    • 168 Days On Market

    Current Estimated Value $528,137

    Last Listing Agent Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
    • /9

      Est $262,125 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

      • 5% Above List Price
      • $203/SF
      • 36 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

  • /28

    $549,000 Sold Jun 26, 2025

    305 Washington Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,476 Sq Ft
    • Built 1930

    Last Sold Summary

    • $222/SF
    • 0 Days On Market

    Current Estimated Value $586,449

    Last Listing Agent William Norris Select Land & Homes, LLC

    305 Washington Ave, Chestertown, MD 21620
    • /44

      Est $658,422 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

      • 2% Above List Price
      • $287/SF
      • 372 Days On Market

      Last Sold Price $645,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /49

    $840,000 Sold Jun 27, 2025

    26865 Mallard Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,355 Sq Ft
    • Built 1963

    Last Sold Summary

    • $250/SF
    • 182 Days On Market

    Current Estimated Value $944,061

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    26865 Mallard Rd, Chestertown, MD 21620
    • /13

      Est $835,611 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

      • 12% Above List Price
      • $225/SF

      Last Sold Price $749,000

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /45

    $459,000 Sold Jun 23, 2025

    811 S Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $476,981

    Last Listing Agent Christine Leonard Redfin Corp

    811 S Meadowview Dr, Chestertown, MD 21620
    • /50

      Est $1,402,647 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

      • 8% Above List Price
      • $389/SF
      • 18 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Glenn Sutton TTR Sotheby's International Realty

  • /24

    $285,000 Sold Aug 08, 2025

    117 N Water St Unit 3B, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft
    • Built 1886

    Last Sold Summary

    • $437/SF
    • 457 Days On Market

    Current Estimated Value $782,891

    Last Listing Agent John Burke Gunther-McClary Real Estate

    117 N Water St Unit 3B, Chestertown, MD 21620
    • /30

      Est $401,934 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

      • 15% Above List Price
      • $208/SF
      • 1 Day On Market

      Last Sold Price $350,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /42

    $260,000 Sold Feb 18, 2026

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1954

    Last Sold Summary

    • $230/SF
    • 170 Days On Market

    Current Estimated Value $277,870

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
    • /69

      Est $539,412 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

      • 14% Above List Price
      • $148/SF
      • 10 Days On Market

      Last Sold Price $475,000

      Last Listing Agent Chase Broadhurst EXP Realty, LLC

  • /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 $148,275

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620

Showing Results 321 - 360, Page 9 of 18

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