7,017

Homes in ZIP Code 21620

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  • 3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    /18

    $636,383 Sold Apr 24, 2025

    3650 Gratitude Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,599 Sq Ft
    • Built 2025

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Last Listing Agent Tineshia Johnson NVR, INC.

    3650 Gratitude Way, Chestertown, MD 21620
    • 335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      335 Devon Dr, Chestertown, MD 21620
      /44

      Est $540,192 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
  • 10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    /94

    $1,495,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 5,241 Sq Ft

    10800 Cliff Rd, Chestertown, MD 21620

    Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The

    Lona Todd Taylor Properties

    10800 Cliff Rd, 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 $372,976

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    117 Court St, 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
  • 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 $215,279

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, 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 $646,395 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
  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000 Pending

    • 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 $252,766

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • 331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      /33

      Est $922,095 Not Listed For Sale

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

      331 Park Ln, Chestertown, MD 21620

      331 Park Ln, 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
  • 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 $572,064

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      /23

      Est $335,398 Not Listed For Sale

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

      228 Dutchess Rd, Chestertown, MD 21620

      228 Dutchess Rd, 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
  • 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
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      /11

      Est $305,297 Not Listed For Sale

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

      102 Darden Rd, Chestertown, MD 21620

      102 Darden Rd, Chestertown, MD 21620
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $350,000

    • 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
  • 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
    • 310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      /27

      Est $341,413 Not Listed For Sale

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

      310 Longfellow Dr, Chestertown, MD 21620

      310 Longfellow Dr, Chestertown, MD 21620
  • 213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    213 Central Dr, Chestertown, MD 21620
    /23

    $314,900

    • 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
  • 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

    Current Estimated Value $693,305

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec 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 $378,774 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
  • 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
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    /7

    $80,000 Sold Dec 22, 2025

    5700 Johnsontown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1900

    Last Sold Summary

    • $70/SF
    • 107 Days On Market

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • 122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      /8

      Est $229,259 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft

      122 1st St, Chestertown, MD 21620

      122 1st St, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    /16

    $165,000

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft

    141 Prospect St, Chestertown, MD 21620

    INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find!Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something

    Jeff Guthrie Taylor Properties

    141 Prospect St, 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 $61,500

    Last Listing Agent William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • 204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      /35

      Est $361,781 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft

      204 Princess Anne Dr, Chestertown, MD 21620

      204 Princess Anne Dr, 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
  • 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

    Current Estimated Value $299,479

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
    • 201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      /36

      Est $390,817 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft

      201 Princess Anne Dr, Chestertown, MD 21620

      201 Princess Anne 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
  • 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 $108,688

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • 124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      /18

      Est $293,957 Not Listed For Sale

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

      124 Wilton Rd, Chestertown, MD 21620

      124 Wilton Rd, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /11

    $212,000

    • Land
    • 10.05 Acres
    • $21,095 per Acre

    0 Hoffecker Rd, Chestertown, MD 21620

    Discover a rare opportunity to create your future home on this beautiful parcel of land, set in a peaceful and scenic setting. With ample space and flexibility, the property offers endless possibilities for a custom build, from a cozy retreat to a thoughtfully designed estate. Enjoy the tranquility of country living while remaining conveniently close to local shops, dining, and nearby routes for

    Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
  • 25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    /53

    $375,000 Sold Apr 16, 2025

    25740 Collins Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,389 Sq Ft
    • Built 1956

    Last Sold Summary

    • $111/SF
    • 29 Days On Market

    Current Estimated Value $405,125

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • 121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      /33

      Est $726,920 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,327 Sq Ft

      121 Lyons Ln, Chestertown, MD 21620

      121 Lyons Ln, 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
  • 8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    /47

    $700,000 Sold Dec 04, 2025

    8951 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2014

    Last Sold Summary

    • $187/SF
    • 2 Days On Market

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

Maryland Kent County Chestertown 21620

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