6,952

Homes in ZIP Code 21620

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  • /30

    $295,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,132 Sq Ft

    240 Round Top Rd, Chestertown, MD 21620

    Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy light filled living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced

    Karen Clark Clark & Co Realty, LLC

    240 Round Top 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

    Current Estimated Value $110,666

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
    • /27

      Not Listed For Sale

      1106 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1973
      1106 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Clint Evans Cross Street Realtors LLC

  • /10

    $259,900

    New Construction Open Thu 6PM - 7PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    115 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This interior unit 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

    115 Metcalf Rd, 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 $179,564

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
    • /33

      Est $686,887

      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

      • 0 Days On Market

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /6

    $5,000

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

    0 Beltram Rd, Chestertown, 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 @ 9:00 AM. The list price is the suggested opening bid. Deposit: $5,000.This lot of land is located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram Rd, Chestertown, MD 21620
  • /41

    $465,000

    Sold Aug 14, 2026

    311 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,504 Sq Ft
    • Built 2007

    Last Sold Summary

    • $133/SF
    • 216 Days On Market

    Current Estimated Value $495,143

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
    • /22

      Est $324,325

      Not Listed For Sale

      201 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 1985
      201 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /24

    $799,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, 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 $302,290

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

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

      Est $818,960

      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

      • 9 Days On Market

      Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

  • /3

    $69,900

    $15K PRICE DROP
    • Land
    • 4.03 Acres
    • $17,345 per Acre

    8886 Georgetown Rd, Georgetown, MD 21620

    Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a rare combination of privacy, recreation, and convenience. Whether you're seeking a peaceful retreat, hunting property, or camping getaway, this versatile parcel offers endless opportunities. Enjoy the tranquility of nature,

    TAMMY GREEN Samson Properties

    8886 Georgetown Rd, Georgetown, MD 21620
  • /41

    $330,000

    Sold Mar 31, 2026

    129 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1985

    Last Sold Summary

    • $282/SF
    • 41 Days On Market

    Current Estimated Value $326,773

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma Rd, Chestertown, MD 21620
    • /31

      Est $294,452

      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

      • 5 Days On Market

      Last Listing Agent Kerry D'Azevedo Integrity Real Estate

  • /35

    $349,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    23208 Buck Neck Rd, Chestertown, MD 21620

    Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price.Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and

    David Moore Real Broker, LLC

    23208 Buck Neck Rd, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jun 17, 2026

    202 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,427 Sq Ft
    • Built 1956

    Last Sold Summary

    • $228/SF
    • 0 Days On Market

    Current Estimated Value $327,383

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620
    • /23

      Est $306,838

      Not Listed For Sale

      107 Dutchess Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 2005
      107 Dutchess Rd, Chestertown, MD 21620

      Last Sold Summary

      • 234 Days On Market

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • /27

    $385,000

    • 4 Beds
    • 3 Baths
    • 2,630 Sq Ft

    23043 Bay Shore Spur, Chestertown, MD 21620

    Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

    Robin Fithian Rock Hall Properties Real Estate

    23043 Bay Shore Spur, 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 $714,866

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /25

      Est $370,245

      Not Listed For Sale

      149 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,811 Sq Ft
      • Built 1982
      149 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Mr. Isaac Bahary KW Empower

  • /21

    $269,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10540 Tonopah Rd, Chestertown, MD 21620

    Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

    Michele Palmer Doug Ashley Realtors, LLC

    10540 Tonopah Rd, Chestertown, MD 21620
  • /12

    $50,000

    Sold Apr 29, 2026

    144 Char Nor Manor Blvd, Chestertown, MD 21620

    • Land
    • 22,651 Sq Ft
    • $96,154 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 6 Days On Market

    Current Estimated Value $53,291

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    144 Char Nor Manor Blvd, Chestertown, MD 21620
    • /53

      Est $486,599

      Not Listed For Sale

      123 Burchard Sawmill Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,648 Sq Ft
      • Built 1918
      123 Burchard Sawmill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Crystal Pickett EXP Realty, LLC

  • /2

    $15,000

    • Land
    • 22,651 Sq Ft
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • /2

    $35,000

    Sold Mar 20, 2026

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 14,374 Sq Ft
    • $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
    • /36

      Est $375,539

      Not Listed For Sale

      114 Ryan Ct, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,496 Sq Ft
      • Built 1978
      114 Ryan Ct, Chestertown, MD 21620

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Julie Santoboni Taylor Properties

  • /45

    $424,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    8630 Elm Rd, Chestertown, MD 21620

    Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore.The home offers five generously sized bedrooms, providing comfortable space for family,

    Lawrence Lessin Save 6, Incorporated

    8630 Elm Rd, Chestertown, MD 21620
  • /2

    $180,000

    Sold Mar 27, 2026

    9925 Flatland Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft
    • Built 1900

    Last Sold Summary

    • 26% Above List Price
    • $132/SF

    Current Estimated Value $186,516

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • /21

      Est $298,400

      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

      • 13 Days On Market

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /2

    $263,000

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

    115 Chester Arms Dr, Chestertown, MD 21620

    Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own.The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown

    Jarnell Foster Samson Properties

    115 Chester Arms Dr, Chestertown, MD 21620
  • /6

    $55,000

    Sold Aug 21, 2026

    110 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft
    • Built 1900

    Last Sold Summary

    • 54% Below List Price
    • $25/SF
    • 65 Days On Market

    Current Estimated Value $109,211

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
    • /22

      Est $361,267

      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

      • 3 Days On Market

      Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

  • /2

    $5,000

    $7K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $14,706 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    Investors- this lot could possibly have public utilities available in the future! Currently a recreational lot that can be used to garden or an extension of neighboring property. Perc test failed and not currently buildable.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Kinglet Rd, 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 $410,371

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • /30

      Est $597,990

      Not Listed For Sale

      411 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1977
      411 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /24

    $765,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • /49

    $392,500

    Sold Jan 28, 2026

    108 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Above List Price
    • $228/SF
    • 76 Days On Market

    Current Estimated Value $397,209

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
    • /41

      Est $333,631

      Not Listed For Sale

      6744 Church Hill Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,298 Sq Ft
      • Built 1964
      6744 Church Hill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 199 Days On Market

      Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

  • /43

    $499,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft

    1003 Twin Ct, Chestertown, MD 21620

    Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and

    Jody Baker Cross Street Realtors LLC

    1003 Twin Ct, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 18

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