6,914

Kent, MD Homes

Section Image
    • 117 High St, Chestertown, MD 21620
      117 High St, Chestertown, MD 21620
      117 High St, Chestertown, MD 21620
      /56

      Est $891,687 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
  • 332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    /29

    $252,400 Sold Aug 12, 2024

    • 1,408 Sq Ft
    • $179/SF
    • 118 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    332 Truslow Rd, Chestertown, MD 21620

    Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a

    James Blackwell Blackwell Real Estate, LLC

    332 Truslow Rd, Chestertown, MD 21620
    • 10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      /17

      Est $274,714 Not Listed For Sale

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

      10355 Bunting Rd, Chestertown, MD 21620

      10355 Bunting Rd, Chestertown, MD 21620
  • 415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    /24

    $718,000 Sold Aug 09, 2024

    • 1,376 Sq Ft
    • $522/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    415 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the

    Richard Budden Coldwell Banker Chesapeake Real Estate Company

    415 Fairview Dr, Chestertown, MD 21620
    • 225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      /38

      Est $612,162 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 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    /2

    $40,000 Sold Aug 05, 2024

    • Land
    • 4.03 Acres
    • $9,926 per Acre
    • 26 Days On Market

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620

    Wow 4 acres of privacy and public utilities available! Located just outside of Chestertown in Fairlee. Accessible through a 50' right of way shown in survey. Buyer to verify right of way and utilities. Call today!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    • 202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      202 Calvert St, Chestertown, MD 21620
      /32

      Est $494,751 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
  • 209 N Water St, Chestertown, MD 21620
    209 N Water St, Chestertown, MD 21620
    /2

    $1,100,000 Sold Jun 30, 2025

    • 2,909 Sq Ft
    • $378/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1900

    209 N Water St, Chestertown, MD 21620

    One of the "stand-out" North Water Street waterfront homes in Historic Chestertown that has raised children, hosted town development meetings, entertained many, and most recently provided the perfect escape for a loving three-generation family. The house is "old bones with refreshed skin" in many parts of this three-story traditional Four Square and full, multi-room basement. What distinguishes

    Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $313,167 Not Listed For Sale

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

      23240 Clarissa Rd, Chestertown, MD 21620

      23240 Clarissa Rd, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /2

    $539,000 Sold Jun 16, 2025

    • 3,050 Sq Ft
    • $177/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1879

    107 N Queen St, Chestertown, MD 21620

    The Vannort House stands proudly on historic Queen Street with a colonial-era smokehouse in the yard! Light & breezy: The 31' long screened-in side-porch has doors from the eat-in Kitchen, formal Dining Room, and the grand high-ceilinged Living Room! Keep all the doors open into the screened porch for an amazing indoor-outdoor way of living! A truly versatile layout for entertaining and

    Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $255,538 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 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    • Land
    • 13 Acres
    • $6,686 per Acre
    • 0 Days On Market

    0 None Unit MDKE2005014, Chestertown, MD 21620

    13.5 wooded acres with very limited access on north side of Chestertown. Should be excellent deer hunting. 16' paper right of way to access.

    William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $311,715 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
  • 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
    • 223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      /47

      Est $615,302 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
  • 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
    • 1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      /18

      Est $415,776 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 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
    • 8616 Orchard Dr, Chestertown, MD 21620
      8616 Orchard Dr, Chestertown, MD 21620
      8616 Orchard Dr, Chestertown, MD 21620
      /33

      Est $623,738 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
  • 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
    • 206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      206 Lincoln Dr, Chestertown, MD 21620
      /7

      Est $263,410 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft

      206 Lincoln Dr, Chestertown, MD 21620

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

      Est $420,058 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
  • 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
    • 212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      /45

      Est $317,265 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
  • 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
    • 5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      /31

      Est $892,731 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
  • 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
    • 8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      /26

      Est $292,833 Not Listed For Sale

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

      8890 Fairlee Rd, Chestertown, MD 21620

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

      Est $1,059,079 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
  • 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
    • 521 High St, Chestertown, MD 21620
      521 High St, Chestertown, MD 21620
      521 High St, Chestertown, MD 21620
      /15

      Est $399,654 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
  • 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
    • 25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      /54

      Est $675,358 Not Listed For Sale

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

      25300 Foxchase Dr, Chestertown, MD 21620

      25300 Foxchase Dr, 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 $297,064 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
    • 1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      /30

      Est $388,628 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,854 Sq Ft

      1 Reed Ct, Chestertown, MD 21620

      1 Reed Ct, Chestertown, MD 21620
    • 8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      /52

      Est $684,054 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 $359,798 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
    • 23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      /24

      Est $346,202 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,088 Sq Ft

      23795 Lands End Rd, Chestertown, MD 21620

      23795 Lands End Rd, Chestertown, MD 21620

Showing Results 481 - 520, Page 13 of 18

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