7,032

Homes in ZIP Code 21620

Section Image
    • /27

      Est $342,811 Not Listed For Sale

      310 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 2002
      310 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $205/SF
      • 20 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /16

    $170,000

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    107 Conley Dr, Chestertown, MD 21620

    Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and flooring . Call for details and will assist you with your dream of owning your own home.

    Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, Chestertown, MD 21620
  • /2

    $11,000 Sold Feb 19, 2026

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    • Land
    • 2 Acres
    • $5,500 per Acre

    Last Sold Summary

    • 806 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    • /42

      Est $383,457 Not Listed For Sale

      414 Pine Tree Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft
      • Built 1968
      414 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $207/SF
      • 47 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Kimberly Raeder Keller Williams Select Realtors of Annapolis

  • /24

    $419,900

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

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors,

    Jeff Guthrie Taylor Properties

    109 S College Ave, 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 $128,694

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • /8

      Est $204,287 Not Listed For Sale

      122 1st St, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1955
      122 1st St, Chestertown, MD 21620

      Last Sold Summary

      • 51% Above List Price
      • $188/SF
      • 5 Days On Market

      Last Sold Price $135,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /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
  • /47

    $359,000 Sold Feb 03, 2026

    8833 Georgetown Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 1900

    Last Sold Summary

    • $221/SF
    • 76 Days On Market

    Current Estimated Value $354,000

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
    • /35

      Est $371,519 Not Listed For Sale

      204 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1984
      204 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $239/SF
      • 82 Days On Market

      Last Sold Price $359,000

      Last Listing Agent Jamil Wright EXP Realty, LLC

  • /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
  • /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 $735,193

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
    • /36

      Est $404,932 Not Listed For Sale

      201 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 1998
      201 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $177/SF
      • 120 Days On Market

      Last Sold Price $370,247

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • /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
  • /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

    Current Estimated Value $137,102

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • /18

      Est $308,436 Not Listed For Sale

      124 Wilton Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1976
      124 Wilton Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $275/SF
      • 9 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Jeff Guthrie Taylor Properties

  • /48

    $1,395,500 Open Sat 11AM - 1PM

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

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /20

    $125,000 Sold Mar 02, 2026

    423 Calvert St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1992

    Last Sold Summary

    • $110/SF
    • 112 Days On Market

    Current Estimated Value $136,189

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
    • /33

      Est $696,944 Not Listed For Sale

      317 Union Church Rd, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,512 Sq Ft
      • Built 2021
      317 Union Church Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $273/SF
      • 0 Days On Market

      Last Sold Price $685,000

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /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
  • /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 $134,000

    Last Listing Agent William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • /33

      Est $733,084 Not Listed For Sale

      121 Lyons Ln, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,327 Sq Ft
      • Built 1990
      121 Lyons Ln, Chestertown, MD 21620

      Last Sold Summary

      • 2% Below List Price
      • $322/SF
      • 22 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Jennifer Gregorski Washington Fine Properties

  • /2

    $3,000

    • Land
    • 0.34 Acre
    • $8,824 per Acre

    0 Tonopah Rd Unit MDKE2006286, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 4/15/2026 @ 10:00 AM. Bidding ends 4/17/2026 @ 11:35 AM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major

    Adam Shpritz Ashland Auction Group LLC

    0 Tonopah Rd Unit MDKE2006286, 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 $304,904

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
    • /12

      Est $756,954 Not Listed For Sale

      204 Truslow Farm Ln, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,945 Sq Ft
      • Built 1917
      204 Truslow Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 24% Below List Price
      • $340/SF
      • 9 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

  • /2

    $29,000

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota 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 $157,484

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • /31

      Est $285,520 Not Listed For Sale

      150 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      150 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $251/SF
      • 5 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Kerry D'Azevedo Integrity Real Estate

  • /34

    $675,000 Pending

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, 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 $444,963

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • /26

      Est $400,340 Not Listed For Sale

      200 Duke of Kent St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,477 Sq Ft
      • Built 1995
      200 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $251/SF
      • 4 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /17

    $259,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    107 Metcalfe Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in this Right Now. This home features luxuryvinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granitecountertops, 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

    David Moore Real Broker, LLC

    107 Metcalfe Rd, 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

    Current Estimated Value $701,290

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /42

      Est $319,572 Not Listed For Sale

      103 Creston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1973
      103 Creston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Below List Price
      • $304/SF
      • 6 Days On Market

      Last Sold Price $332,100

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /2

    $9,500

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

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • /2

    $35,000 Sold Mar 20, 2026

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 0.33 Acre
    • $106,061 per Acre

    Last Sold Summary

    • 756 Days On Market

    Last Listing Agent Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
    • /21

      Est $304,837 Not Listed For Sale

      116 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,028 Sq Ft
      • Built 1976
      116 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • $297/SF
      • 13 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /35

    $413,300 Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Current Estimated Value $407,136

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • /22

      Est $335,301 Not Listed For Sale

      218 Concord Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1997
      218 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Below List Price
      • $285/SF
      • 3 Days On Market

      Last Sold Price $342,000

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

Showing Results 121 - 160, Page 4 of 18

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