6,952

Homes in ZIP Code 21620

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    • /87

      Est $412,785

      Not Listed For Sale

      312 Princess Anne Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 1,848 Sq Ft
      • Built 1987
      312 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /4

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Towhee Rd, Chesapeake Landing, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:15 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 all the attractions in Chestertown, Maryland. It offers

    Adam Shpritz Ashland Auction Group LLC

    0 Towhee Rd, Chesapeake Landing, MD 21620
  • /47

    $330,000

    Sold Sep 14, 2026

    8312 Broad Neck Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 3,292 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Below List Price
    • $100/SF
    • 14 Days On Market

    Current Estimated Value $419,018

    Last Listing Agent Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, Chestertown, MD 21620
    • /80

      Est $407,394

      Not Listed For Sale

      221 River Rd, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1969
      221 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

  • /34

    $440,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,058 Sq Ft

    104 Church Aly, Chestertown, MD 21620

    A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Church Aly, Chestertown, MD 21620
  • /29

    $330,000

    Sold Apr 03, 2026

    23110 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft
    • Built 1938

    Last Sold Summary

    • $183/SF
    • 174 Days On Market

    Current Estimated Value $321,904

    Last Listing Agent Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • /48

      Est $391,560

      Not Listed For Sale

      125 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,102 Sq Ft
      • Built 1976
      125 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /36

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    217 Edmore Rd, Chestertown, MD 21620

    Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then.Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings.

    Michele Palmer Doug Ashley Realtors, LLC

    217 Edmore Rd, Chestertown, MD 21620
  • /6

    $5,000

    Sold Jan 08, 2026

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    • Land
    • 18,295 Sq Ft
    • $11,905 per Acre

    Last Sold Summary

    • 230 Days On Market

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    • /42

      Est $399,295

      Not Listed For Sale

      210 Rosin Dr, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,352 Sq Ft
      • Built 1987
      210 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Stacey Stracke Douglas Realty, LLC

  • /2

    $24,000

    $4K PRICE INCREASE
    • Land
    • 21,780 Sq Ft
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    23710 L Rd, Chestertown, MD 21620
  • /47

    $355,000

    Sold May 26, 2026

    349 & 351 High St, Chestertown, MD 21620

    • Studio
    • 3,664 Sq Ft
    • Built 1900

    Last Sold Summary

    • $97/SF
    • 496 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
    • /57

      Est $535,025

      Not Listed For Sale

      126 Hilltop Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,733 Sq Ft
      • Built 2001
      126 Hilltop Dr, Chestertown, MD 21620

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Chardae Eduruke Real Broker LLC

  • /52

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    216 Birch Run Rd, Chestertown, MD 21620

    Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A

    Liddy Campbell TTR Sotheby's International Realty

    216 Birch Run Rd, Chestertown, MD 21620
  • /25

    $334,000

    Sold Apr 06, 2026

    8750 Georgetown Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2014

    Last Sold Summary

    • $176/SF
    • 134 Days On Market

    Current Estimated Value $345,868

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
    • /62

      Est $397,210

      Not Listed For Sale

      216 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1986
      216 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Brett Schrader Taylor Properties

  • /26

    $340,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • /49

    $552,000

    Sold Apr 17, 2026

    216 Blakefield Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $230/SF
    • 94 Days On Market

    Current Estimated Value $553,966

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
    • /26

      Est $393,766

      Not Listed For Sale

      224 Spring Rd, Millington, MD 21651

      224 Spring Rd, Millington, MD 21651

      Last Sold Summary

      • 171 Days On Market

      Last Listing Agent Rob Freyer Charis Realty Group

  • /25

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • /15

    $555,000

    Sold Jan 12, 2026

    26933 Mallard Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1956

    Last Sold Summary

    • $347/SF
    • 77 Days On Market

    Current Estimated Value $569,669

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
    • /8

      Est $1,185,008

      Not Listed For Sale

      545 Fey Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft
      • Built 1948
      545 Fey Rd, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /50

    $448,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile.

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • /31

    $310,000

    Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $314,902

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • /18

      Est $329,276

      Not Listed For Sale

      120 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1986
      120 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

  • /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /72

    $1,200,000

    Sold Aug 14, 2026

    202 Royston Shores Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 1968

    Last Sold Summary

    • $524/SF
    • 16 Days On Market

    Current Estimated Value $1,175,998

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    202 Royston Shores Rd, Chestertown, MD 21620
    • /16

      Est $344,564

      Not Listed For Sale

      102 Concord Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2023
      102 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. 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 walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • /18

    $620,000

    Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Current Estimated Value $636,337

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • /80

      Est $586,771

      Not Listed For Sale

      118 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,248 Sq Ft
      • Built 1985
      118 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /2

    $38,000

    $17K PRICE INCREASE
    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • /12

    $146,000

    Sold Sep 08, 2026

    7224 Rock Hall Rd, Rock Hall, MD 21661

    • Land
    • 2.15 Acres
    • $67,907 per Acre

    Last Sold Summary

    • 320 Days On Market

    Current Estimated Value $156,729

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
    • /28

      Est $433,705

      Not Listed For Sale

      209 Myers Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,846 Sq Ft
      • Built 1996
      209 Myers Rd, Chestertown, MD 21620

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /4

    $5,000

    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Bunting Rd, 6, Fairlee, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:05 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 all the attractions in Chestertown, Maryland. It offers

    Adam Shpritz Ashland Auction Group LLC

    0 Bunting Rd, 6, Fairlee, MD 21620
  • /41

    $740,000

    Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Current Estimated Value $759,066

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
    • /43

      Est $393,040

      Not Listed For Sale

      129 Char Nor Manor Blvd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1961
      129 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

  • /2

    $50,000

    • Land
    • 23,958 Sq Ft
    • $90,909 per Acre

    0 Towhee Rd, Chesapeake Landing, MD 21620

    This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. 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.

    Dustin Parker The Parker Group

    0 Towhee Rd, Chesapeake Landing, MD 21620
  • /2

    $325,000

    Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $357,407

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
    • /6

      Est $726,868

      Not Listed For Sale

      305 Hickory Ln, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 2,627 Sq Ft
      • Built 1998
      305 Hickory Ln, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

Showing Results 241 - 280, Page 7 of 18

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