6,895

Chestertown, MD Homes

Section Image
  • 226 Blakefield Dr, Chestertown, MD 21620
    226 Blakefield Dr, Chestertown, MD 21620
    /2

    $539,000 Sold Mar 31, 2025

    • 2,400 Sq Ft
    • $225/SF
    • 4 Beds
    • 3 Baths
    • Built 2025

    226 Blakefield Dr, Chestertown, MD 21620

    New Construction Sold in the Blakefield Community . 4 Bedrooms, 3 Full Baths

    datacorrect BrightMLS Non Subscribing Office

    226 Blakefield Dr, Chestertown, MD 21620
    • 411 Greenwood Ave, Chestertown, MD 21620
      411 Greenwood Ave, Chestertown, MD 21620
      411 Greenwood Ave, Chestertown, MD 21620
      /45

      Est $423,348 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,676 Sq Ft

      411 Greenwood Ave, Chestertown, MD 21620

      411 Greenwood Ave, Chestertown, MD 21620
  • 833 Woods Rd, Chestertown, MD 21620
    833 Woods Rd, Chestertown, MD 21620
    /2

    $155,000 Sold Dec 17, 2024

    • Land
    • 3.00 Acres
    • $51,667 per Acre
    • 13 Days On Market

    833 Woods Rd, Chestertown, MD 21620

    Nice wooded 3-acre lot to build your dream home! Close to Chestertown and Rt 301 for commuters. The lot has perc and septic already exists. Some of the lot has been cleared where home can be built.

    Tina Brown Benson & Mangold, LLC

    833 Woods Rd, Chestertown, MD 21620
    • 27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      /45

      Est $555,065 Not Listed For Sale

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

      27325 Preston Ln, Chestertown, MD 21620

      27325 Preston Ln, Chestertown, MD 21620
  • 0 Glenola Rd, Chestertown, MD 21620
    0 Glenola Rd, Chestertown, MD 21620
    /2

    $20,000 Sold Dec 13, 2024

    • Land
    • 0.35 Acre
    • $57,143 per Acre
    • 112 Days On Market

    0 Glenola Rd, Chestertown, MD 21620

    Perc approved lot for sale in Chesapeake Landing. A total of .34 combined with both lots. Community has a voluntary HOA giving you access to the boat ramp, marina and a slip for an extra fee.

    John Burke Gunther-McClary Real Estate

    0 Glenola Rd, Chestertown, MD 21620
    • 117 High St, Chestertown, MD 21620
      117 High St, Chestertown, MD 21620
      117 High St, Chestertown, MD 21620
      /56

      Est $853,206 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,226 Sq Ft

      117 High St, Chestertown, MD 21620

      117 High St, Chestertown, MD 21620
  • 7517 Sunburst Ave, Chestertown, MD 21620
    7517 Sunburst Ave, Chestertown, MD 21620
    /2

    $254,900 Sold Nov 27, 2024

    • 1,320 Sq Ft
    • $193/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2020

    7517 Sunburst Ave, Chestertown, MD 21620

    Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan. Open kitchen living space features LVP flooring, kitchen island, stainless steel appliances, and large windows with lots of sunlight streaming in! Come check it out today!

    John Carroll Village Real Estate Company LLC

    7517 Sunburst Ave, Chestertown, MD 21620
    • 10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      /17

      Est $272,122 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      10355 Bunting Rd, Chestertown, MD 21620

      10355 Bunting Rd, Chestertown, MD 21620
  • 340 Cannon St, Chestertown, MD 21620
    340 Cannon St, Chestertown, MD 21620
    /2

    $255,000 Sold Nov 15, 2024

    • 1,582 Sq Ft
    • $161/SF
    • 4 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1920

    340 Cannon St, Chestertown, MD 21620

    Location! Location! Location! *** Great Investment Opportunity *** Just one block from the heart of Historic Chestertown, this spacious victorian home is waiting for your personal touch and TLC. Property has 3 bedrooms, 1 full bathroom (on the upper level) and 1 half bathroom (on the main level). This home also offers an amazing element of surprise in the attic space which can be converted

    Kysha Merritt Samson Properties

    340 Cannon St, Chestertown, MD 21620
    • 225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      /38

      Est $605,778 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,749 Sq Ft

      225 Richard Dr, Chestertown, MD 21620

      225 Richard Dr, Chestertown, MD 21620
  • 0 Fall St Unit MDKE2004200, Chestertown, MD 21620
    0 Fall St Unit MDKE2004200, Chestertown, MD 21620
    /2

    $6,000 Sold Nov 07, 2024

    • Land
    • 0.31 Acre
    • $19,355 per Acre
    • 62 Days On Market

    0 Fall St Unit MDKE2004200, Chestertown, MD 21620

    Six lots combined into one .3 acre property. Walking distance to the Chesapeake Bay, Tolchester beach, marina and Shanty. The county says sewer hook up is not available.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Fall St Unit MDKE2004200, Chestertown, MD 21620
    • 202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      /32

      Est $493,913 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,988 Sq Ft

      202 Calvert St, Chestertown, MD 21620

      202 Calvert St, Chestertown, MD 21620
  • 211 N Lynchburg St, Chestertown, MD 21620
    211 N Lynchburg St, Chestertown, MD 21620
    /2

    $7,200 Sold Oct 31, 2024

    • Land
    • 0.03 Acre
    • $240,000 per Acre
    • 35 Days On Market

    211 N Lynchburg St, Chestertown, MD 21620

    This 20'x64' lot is located just outside of downtown Chestertown attractions. A Chesterown zoning administrator said "A prospective buyer would have to get a variance from the Board of Zoning Appeals, which would almost certainly be granted. " Public utilities are available. Priced to sell!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    211 N Lynchburg St, Chestertown, MD 21620
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $288,462 Not Listed For Sale

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

      23240 Clarissa Rd, Chestertown, MD 21620

      23240 Clarissa Rd, Chestertown, MD 21620
  • 241 Duke of Kent St, Chestertown, MD 21620
    241 Duke of Kent St, Chestertown, MD 21620
    /2

    $369,000 Sold Aug 05, 2024

    • 1,494 Sq Ft
    • $247/SF
    • 3 Beds
    • 2 Baths
    • Built 1999

    241 Duke of Kent St, Chestertown, MD 21620

    Well maintained home in Queen Anne's County featuring 3 bedrooms, 2 full baths, separate dining room as well as an eat-in kitchen. Full size laundry room with exterior exit to the partially fenced back yard and an oversized 2 car garage with room for vehicles and storage. The entire home has been freshly painted and has all new carpet, and new flooring in the kitchen, laundry, and bathrooms.

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    241 Duke of Kent St, Chestertown, MD 21620
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $242,000 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,152 Sq Ft

      306 Roosevelt Dr, Chestertown, MD 21620

      306 Roosevelt Dr, Chestertown, MD 21620
  • 101 Rivershore Rd, Chestertown, MD 21620
    101 Rivershore Rd, Chestertown, MD 21620
    /2

    $1,125,000 Sold Jun 10, 2025

    • 1,968 Sq Ft
    • $572/SF
    • 3 Beds
    • 2 Baths
    • Built 1950

    101 Rivershore Rd, Chestertown, MD 21620

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $307,229 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft

      27370 Morgnec Rd, Chestertown, MD 21620

      27370 Morgnec Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
    /2

    $330,000 Sold Nov 20, 2024

    • Land
    • 41 Acres
    • $8,065 per Acre

    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620

    Jim Bim Winning Edge

    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
    • 223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      /47

      Est $574,785 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,004 Sq Ft

      223 S Queen St, Chestertown, MD 21620

      223 S Queen St, Chestertown, MD 21620
  • 23693 L Rd, Chestertown, MD 21620
    23693 L Rd, Chestertown, MD 21620
    /2

    $18,000 Sold Sep 06, 2024

    • Land
    • 2.00 Acres
    • $9,000 per Acre
    • 409 Days On Market

    23693 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23693 L Rd, Chestertown, MD 21620
    • 1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      /18

      Est $409,044 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,854 Sq Ft

      1005 Twin Ct, Chestertown, MD 21620

      1005 Twin Ct, Chestertown, MD 21620
    • 8616 Orchard Dr, Chestertown, MD 21620
      8616 Orchard Dr, Chestertown, MD 21620
      8616 Orchard Dr, Chestertown, MD 21620
      /33

      Est $625,693 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,422 Sq Ft

      8616 Orchard Dr, Chestertown, MD 21620

      8616 Orchard Dr, Chestertown, MD 21620
    • 206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      /7

      Est $256,266 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      206 Lincoln Dr, Chestertown, MD 21620

      206 Lincoln Dr, Chestertown, MD 21620
    • 106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      /43

      Est $399,480 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft

      106 Devon Dr, Chestertown, MD 21620

      106 Devon Dr, Chestertown, MD 21620
    • 212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      /45

      Est $298,789 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,148 Sq Ft

      212 Rolling Rd, Chestertown, MD 21620

      212 Rolling Rd, Chestertown, MD 21620
    • 5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      /31

      Est $917,324 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,736 Sq Ft

      5598 Langford Bay Rd, Chestertown, MD 21620

      5598 Langford Bay Rd, Chestertown, MD 21620
    • 8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      /26

      Est $289,924 Not Listed For Sale

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

      8890 Fairlee Rd, Chestertown, MD 21620

      8890 Fairlee Rd, Chestertown, MD 21620
    • 109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      /51

      Est $982,129 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,030 Sq Ft

      109 N Water St, Chestertown, MD 21620

      109 N Water St, Chestertown, MD 21620
    • 521 High St, Chestertown, MD 21620
      521 High St, Chestertown, MD 21620
      521 High St, Chestertown, MD 21620
      /15

      Est $390,592 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,356 Sq Ft

      521 High St, Chestertown, MD 21620

      521 High St, Chestertown, MD 21620
    • 25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      /54

      Est $668,678 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,832 Sq Ft

      25300 Foxchase Dr, Chestertown, MD 21620

      25300 Foxchase Dr, Chestertown, MD 21620
    • 103 S Kent St, Chestertown, MD 21620
      103 S Kent St, Chestertown, MD 21620
      103 S Kent St, Chestertown, MD 21620
      /33

      Est $433,798 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,458 Sq Ft

      103 S Kent St, Chestertown, MD 21620

      103 S Kent St, Chestertown, MD 21620
    • 22974 Bay Shore Rd, Chestertown, MD 21620
      22974 Bay Shore Rd, Chestertown, MD 21620
      22974 Bay Shore Rd, Chestertown, MD 21620
      /24

      Est $292,013 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,440 Sq Ft

      22974 Bay Shore Rd, Chestertown, MD 21620

      22974 Bay Shore Rd, Chestertown, MD 21620
    • 10165 John Carvill Rd, Chestertown, MD 21620
      10165 John Carvill Rd, Chestertown, MD 21620
      10165 John Carvill Rd, Chestertown, MD 21620
      /40

      Est $593,857 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,774 Sq Ft

      10165 John Carvill Rd, Chestertown, MD 21620

      10165 John Carvill Rd, Chestertown, MD 21620
    • 8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      /52

      Est $648,580 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,708 Sq Ft

      8623 Orchard Dr, Chestertown, MD 21620

      8623 Orchard Dr, Chestertown, MD 21620
    • 303 E Campus Ave, Chestertown, MD 21620
      303 E Campus Ave, Chestertown, MD 21620
      303 E Campus Ave, Chestertown, MD 21620
      /41

      Est $362,796 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,532 Sq Ft

      303 E Campus Ave, Chestertown, MD 21620

      303 E Campus Ave, Chestertown, MD 21620
    • 3 Reed Ct, Chestertown, MD 21620
      3 Reed Ct, Chestertown, MD 21620
      3 Reed Ct, Chestertown, MD 21620
      /50

      Est $537,640 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,828 Sq Ft

      3 Reed Ct, Chestertown, MD 21620

      3 Reed Ct, Chestertown, MD 21620
    • 114 N Water St, Chestertown, MD 21620
      114 N Water St, Chestertown, MD 21620
      114 N Water St, Chestertown, MD 21620
      /40

      Est $851,996 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,640 Sq Ft

      114 N Water St, Chestertown, MD 21620

      114 N Water St, Chestertown, MD 21620
    • 21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      /22

      Est $217,999 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,064 Sq Ft

      21239 Kansas Ave, Chestertown, MD 21620

      21239 Kansas Ave, Chestertown, MD 21620
    • 214 Richard Dr, Chestertown, MD 21620
      214 Richard Dr, Chestertown, MD 21620
      214 Richard Dr, Chestertown, MD 21620
      /41

      Est $410,403 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,723 Sq Ft

      214 Richard Dr, Chestertown, MD 21620

      214 Richard Dr, Chestertown, MD 21620

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