6,868

Chestertown, MD Homes

Section Image
  • 0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
    /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620

    Welcome to your serene retreat on Tonopah Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Tonopah Rd Unit MDKE2005470, Chestertown, MD 21620
  • 117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    /35

    $365,000 Sold Mar 28, 2025

    117 Court St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 744 Sq Ft
    • Built 1885

    Last Sold Summary

    • $491/SF
    • 23 Days On Market

    Current Estimated Value $371,074

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    117 Court St, Chestertown, MD 21620
    • 101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      101 S Kent St, Chestertown, MD 21620
      /23

      Est $385,349 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft

      101 S Kent St, Chestertown, MD 21620

      101 S Kent St, Chestertown, MD 21620
  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    21111 Texas Ave, Chestertown, MD 21620

    COMING SOON in Tolchester Estates!Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up

    Glory Bee Costa Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
  • 0 Vireo Rd, Chestertown, MD 21620
    0 Vireo Rd, Chestertown, MD 21620
    0 Vireo Rd, Chestertown, MD 21620
    /7

    $12,000 Sold Jan 24, 2025

    0 Vireo Rd, Chestertown, MD 21620

    • Land
    • 0.34 Acre
    • $35,294 per Acre

    Last Sold Summary

    • 239 Days On Market

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    0 Vireo Rd, Chestertown, MD 21620
    • 116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      116 N Queen St, Chestertown, MD 21620
      /54

      Est $630,826 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft

      116 N Queen St, Chestertown, MD 21620

      116 N Queen St, Chestertown, MD 21620
  • 103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    103 Metcalf Rd, Chestertown, MD 21620
    /25

    $259,900 New Construction

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

    103 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this October. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    103 Metcalf Rd, Chestertown, MD 21620
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    /18

    $205,000 Sold Jul 18, 2025

    310 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 2005

    Last Sold Summary

    • $169/SF
    • 24 Days On Market

    Current Estimated Value $208,738

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
    • 107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      107 Adela Way, Chestertown, MD 21620
      /31

      Est $500,649 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft

      107 Adela Way, Chestertown, MD 21620

      107 Adela Way, Chestertown, MD 21620
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    23069 Raleigh Rd, Chestertown, MD 21620

    Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

    George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    /34

    $237,000 Sold Jun 30, 2025

    898 Washington Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • Built 1967

    Last Sold Summary

    • $171/SF
    • 5 Days On Market

    Current Estimated Value $250,238

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • 105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      /43

      Est $430,486 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      105 Sutton Way, Chestertown, MD 21620

      105 Sutton Way, Chestertown, MD 21620
  • LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
  • 23575 Canvasback Rd, Chestertown, MD 21620
    23575 Canvasback Rd, Chestertown, MD 21620
    23575 Canvasback Rd, Chestertown, MD 21620
    /39

    $625,000 Sold Jan 15, 2025

    23575 Canvasback Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,527 Sq Ft
    • Built 2003

    Last Sold Summary

    • $177/SF
    • 97 Days On Market

    Current Estimated Value $650,022

    Last Listing Agent John Burke Gunther-McClary Real Estate

    23575 Canvasback Rd, Chestertown, MD 21620
    • 335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      /44

      Est $513,639 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,874 Sq Ft

      335 Devon Dr, Chestertown, MD 21620

      335 Devon Dr, Chestertown, MD 21620
  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $35,000 Under Contract

    • Land
    • 0.9 Acre
    • $38,889 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • 8774 Orchard Dr, Chestertown, MD 21620
    8774 Orchard Dr, Chestertown, MD 21620
    8774 Orchard Dr, Chestertown, MD 21620
    /36

    $660,000 Sold Dec 16, 2024

    8774 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,444 Sq Ft
    • Built 2003

    Last Sold Summary

    • $192/SF
    • 56 Days On Market

    Current Estimated Value $691,065

    Last Listing Agent Jennifer Thomas RE/MAX Executive

    8774 Orchard Dr, Chestertown, MD 21620
    • 112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      112 Pine Tree Rd, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    /3

    $553,500 Sold Apr 07, 2025

    234 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 2024

    Last Sold Summary

    • $231/SF
    • 0 Days On Market

    Current Estimated Value $561,283

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
    • 118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      /8

      Est $647,224 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,512 Sq Ft

      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      118 Little Harbor Way Unit 102, Chestertown, MD 21620
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $319,900

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

    213 Central Dr, Chestertown, MD 21620

    Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, Chestertown, MD 21620
  • 8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    /59

    $775,000 Sold Nov 08, 2025

    8293 Brices Mill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,836 Sq Ft
    • Built 1900

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
    • 331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      /33

      Est $1,078,357 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft

      331 Park Ln, Chestertown, MD 21620

      331 Park Ln, Chestertown, MD 21620
  • 0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
    /2

    $8,000

    • Land
    • 0.34 Acre
    • $23,529 per Acre

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620

    Welcome to your serene retreat on Cogar Road in charming Chestertown, MD! Nestled on a generous 15,000 square foot lot, this delightful home offers a perfect blend of comfort and leisure. Enjoy the vibrant community atmosphere with access to a fabulous clubhouse and a picturesque marina. Whether you're looking to unwind at home or explore the great outdoors, this property is your gateway to a

    Solomon Zaldivar Compass

    0 Cogar Rd Unit MDKE2005472, Chestertown, MD 21620
  • 209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    /3

    $124,000 Sold Aug 25, 2025

    209 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $122,772 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $125,843

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $356,678 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,796 Sq Ft

      228 Dutchess Rd, Chestertown, MD 21620

      228 Dutchess Rd, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    100 Metcalf Rd, Chestertown, MD 21620

    Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! Your Dream Home Checklist: * NO HOA! Freedom & Savings! * One-Level Living: Easy breezy! * Open Concept: Perfect for entertaining! The heart of the home is the spectacular eat-in

    Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    /32

    $700,000 Sold Oct 22, 2025

    26889 Morgnec Rd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft
    • Built 1966

    Last Sold Summary

    • $356/SF
    • 156 Days On Market

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      /11

      Est $305,503 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft

      102 Darden Rd, Chestertown, MD 21620

      102 Darden Rd, Chestertown, MD 21620
  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /7

    $250,000 Pending

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 113 Pine Cove Ln, Chestertown, MD 21620
    113 Pine Cove Ln, Chestertown, MD 21620
    /2

    $57,500 Sold Apr 30, 2025

    113 Pine Cove Ln, Chestertown, MD 21620

    • Land
    • 0.45 Acre
    • $127,778 per Acre

    Last Sold Summary

    • 185 Days On Market

    Current Estimated Value $61,000

    Last Listing Agent William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • 310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      /27

      Est $338,840 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft

      310 Longfellow Dr, Chestertown, MD 21620

      310 Longfellow Dr, Chestertown, MD 21620
  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    /19

    $300,000 Sold Sep 26, 2025

    925 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $284/SF
    • 50 Days On Market

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
    • 414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      /42

      Est $381,645 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft

      414 Pine Tree Rd, Chestertown, MD 21620

      414 Pine Tree Rd, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /51

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    /4

    $15,000 Sold Jun 02, 2025

    22671 Wood Yard Ln, Chestertown, MD 21620

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $244,000

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • 122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      /8

      Est $193,155 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft

      122 1st St, Chestertown, MD 21620

      122 1st St, Chestertown, MD 21620
  • 404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    /11

    $19,500 Under Contract

    • Land
    • 0.99 Acre
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Kent

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620

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