6,881

Chestertown, MD Homes

Section Image
    • 8999 Orchard Dr, Chestertown, MD 21620
      8999 Orchard Dr, Chestertown, MD 21620
      8999 Orchard Dr, Chestertown, MD 21620
      /51

      Est $716,091 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,478 Sq Ft

      8999 Orchard Dr, Chestertown, MD 21620

      8999 Orchard Dr, Chestertown, MD 21620
  • 21357 Belair Ave, Chestertown, MD 21620
    21357 Belair Ave, Chestertown, MD 21620
    21357 Belair Ave, Chestertown, MD 21620
    /27

    $360,000 Sold May 07, 2024

    • 2,008 Sq Ft
    • $179/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2010

    21357 Belair Ave, Chestertown, MD 21620

    OPEN HOUSE CANCELLED. SELLER HAS ACCEPTED OFFER. 9 year old cape with wonderful open floor plan. Nestled in the woods for privacy. Bay water privileges and marina nearby. This property is part of Tolchester Estates.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    21357 Belair Ave, Chestertown, MD 21620
    • 202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      /32

      Est $477,965 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
  • 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
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $291,613 Not Listed For Sale

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

      23240 Clarissa Rd, Chestertown, MD 21620

      23240 Clarissa Rd, 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
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $244,428 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
  • 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
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $290,862 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
  • 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
    • 223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      /47

      Est $569,774 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
  • 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
    • 1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      /18

      Est $368,013 Not Listed For Sale

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

      1005 Twin Ct, Chestertown, MD 21620

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

      Est $607,014 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
  • 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
    • 206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      /7

      Est $251,426 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      206 Lincoln Dr, Chestertown, MD 21620

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

      Est $393,736 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
  • Lots 233 & 234 Clarissa, Chestertown, MD 21620
    Lots 233 & 234 Clarissa, Chestertown, MD 21620
    /2

    $3,000 Sold May 30, 2024

    • Land
    • 0.46 Acre
    • $6,522 per Acre
    • 501 Days On Market

    Lots 233 & 234 Clarissa, Chestertown, MD 21620

    Opportunity to own property at Chesapeake Landing. Chesapeake Landing has a voluntary HOA which gives you access to the boat ramp and the Chesapeake Bay and Worton Marina. The marina and boat slip are extra. This lot will not perc and cannot be built on per Kent County Health Department.

    Jo Ann Edwards The Hogans Agency

    Lots 233 & 234 Clarissa, Chestertown, MD 21620
    • 212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      /45

      Est $288,946 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
  • 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
    • 5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      /31

      Est $856,609 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
  • 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
    • 8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      /26

      Est $283,309 Not Listed For Sale

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

      8890 Fairlee Rd, Chestertown, MD 21620

      8890 Fairlee Rd, Chestertown, MD 21620
    • 509 N Kent St, Chestertown, MD 21620
      509 N Kent St, Chestertown, MD 21620
      509 N Kent St, Chestertown, MD 21620
      /24

      Est $348,981 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,506 Sq Ft

      509 N Kent St, Chestertown, MD 21620

      509 N Kent St, 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 $962,307 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 $385,292 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 $661,501 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 $417,169 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 $285,413 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 $563,465 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 $650,876 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 $344,107 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 $532,330 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
    • 9827 Breezecroft Ln, Chestertown, MD 21620
      9827 Breezecroft Ln, Chestertown, MD 21620
      9827 Breezecroft Ln, Chestertown, MD 21620
      /34

      Est $1,064,073 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 3,352 Sq Ft

      9827 Breezecroft Ln, Chestertown, MD 21620

      9827 Breezecroft Ln, 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 $796,083 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
    • 211 Mount Vernon Ave, Chestertown, MD 21620
      211 Mount Vernon Ave, Chestertown, MD 21620
      211 Mount Vernon Ave, Chestertown, MD 21620
      /38

      Est $401,210 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,820 Sq Ft

      211 Mount Vernon Ave, Chestertown, MD 21620

      211 Mount Vernon Ave, Chestertown, MD 21620
    • 21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      /22

      Est $222,406 Not Listed For Sale

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

      21239 Kansas Ave, Chestertown, MD 21620

      21239 Kansas Ave, Chestertown, MD 21620
    • 117 N Queen St, Chestertown, MD 21620
      117 N Queen St, Chestertown, MD 21620
      117 N Queen St, Chestertown, MD 21620
      /38

      Est $601,697 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,820 Sq Ft

      117 N Queen St, Chestertown, MD 21620

      117 N Queen St, Chestertown, MD 21620

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