6,890

Chestertown, MD Homes

Section Image
    • /8

      Est $182,384

      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

      • 5 Days On Market

  • /10

    $259,900

    New Construction
    • 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
  • /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 $708,459

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • /35

      Est $392,257

      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

      • 82 Days On Market

  • /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 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:25 PM. 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 is

    Adam Shpritz Ashland Auction Group LLC

    0 Beltram 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
    • /41

      Est $398,488

      Not Listed For Sale

      109 Secor Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1977
      109 Secor Rd, Chestertown, MD 21620

      Last Sold Summary

      • 69 Days On Market

  • /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
  • /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
    • /23

      Est $316,548

      Not Listed For Sale

      104 Dutchess Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,188 Sq Ft
      • Built 1989
      104 Dutchess Rd, Chestertown, MD 21620

      Last Sold Summary

      • 21 Days On Market

  • /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
  • /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 $185,990

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • /36

      Est $410,035

      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

      • 120 Days On Market

  • /70

    $3,000,000

    Under Contract
    • 3 Beds
    • 4 Baths
    • 3,142 Sq Ft

    25440 Learman Rd, Chestertown, MD 21620

    Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2

    Liddy Campbell TTR Sotheby's International Realty

    25440 Learman 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 $407,507

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, 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

  • /47

    $380,000

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

    8312 Broad Neck Rd, Chestertown, MD 21620

    Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment.A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business,

    Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, 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 $392,142

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
    • /18

      Est $310,800

      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

      • 9 Days On Market

  • /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

    $512,500

    Sold Apr 08, 2026

    206 Flyway Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Above List Price
    • $171/SF
    • 5 Days On Market

    Current Estimated Value $508,417

    Last Listing Agent Kristin Lewis Integrity Real Estate

    206 Flyway Ln, Chestertown, MD 21620
    • /33

      Est $702,636

      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

  • /2

    $9,000

    $3K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $26,471 per Acre

    0 Kinglet Rd, Chestertown, MD 21620

    All offers considered! 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
  • /39

    $375,000

    Sold Jan 08, 2026

    7653 Broad Neck Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft
    • Built 1987

    Last Sold Summary

    • $209/SF
    • 41 Days On Market

    Current Estimated Value $395,403

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • /22

      Est $327,959

      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

  • /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
  • /47

    $800,000

    Sold Feb 20, 2026

    4671 Cliffs City Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,783 Sq Ft
    • Built 1967

    Last Sold Summary

    • $449/SF

    Current Estimated Value $794,546

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • /12

      Est $852,860

      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

  • /72

    $1,200,000

    Pending
    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft

    202 Royston Shores Rd, Chestertown, MD 21620

    Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living.Unlike many waterfront properties, the level lot provides easy access from the home to

    Jody Baker Cross Street Realtors LLC

    202 Royston Shores Rd, Chestertown, MD 21620
  • /27

    $376,000

    Sold May 19, 2026

    136 Hilltop Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1995

    Last Sold Summary

    • 3% Above List Price
    • $263/SF
    • 5 Days On Market

    Current Estimated Value $376,815

    Last Listing Agent Joie White Northrop Realty

    136 Hilltop Dr, Chestertown, MD 21620
    • /31

      Est $290,291

      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

  • /42

    $335,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    10720 Foreston Rd, Chestertown, MD 21620

    Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow

    Kathleen Eder Compass

    10720 Foreston Rd, Chestertown, MD 21620
  • /67

    $490,000

    Sold May 08, 2026

    100 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft
    • Built 2008

    Last Sold Summary

    • $129/SF
    • 182 Days On Market

    Current Estimated Value $523,357

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
    • /25

      Est $381,193

      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

  • /23

    $350,000

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft

    117 N Water St Unit 2B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2B, Chestertown, MD 21620
  • /19

    $249,000

    Sold Jun 12, 2026

    112 Elm St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Below List Price
    • $184/SF
    • 14 Days On Market

    Current Estimated Value $271,070

    Last Listing Agent Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
    • /53

      Est $491,141

      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

  • /39

    $515,000

    Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    101 S Mill St, Chestertown, MD 21620

    This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • /66

    $868,000

    Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Current Estimated Value $866,053

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • /26

      Est $412,216

      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

      • 4 Days On Market

Showing Results 161 - 200, Page 5 of 18

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