6,896

Chestertown, MD Homes

Section Image
  • 0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620
    /3

    $3,000

    • Land
    • 14,810 Sq Ft
    • $8,824 per Acre

    0 Cogar Rd Unit MDKE2006304, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins5/14/2026 @ 10:00 AM. Bidding ends 5/18/2026 @ 12:40 PM. 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 Cogar Rd Unit MDKE2006304, 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

    Current Estimated Value $130,944

    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 $185,781

      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

      • 38% Above List Price
      • $188/SF
      • 5 Days On Market
      • Last Sold Price $135,000
      • May 22, 2024

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,200,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck 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 $306,991

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, 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 $356,507

      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

      • 1% Below List Price
      • $239/SF
      • 82 Days On Market
      • Last Sold Price $359,000
      • Nov 08, 2024

      Last Listing Agent Jamil Wright EXP Realty, LLC

  • 126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    126 Char Nor Manor Blvd, Chestertown, MD 21620
    /36

    $349,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a

    Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, 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
    • 20,908 Sq Ft
    • $31,250 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $157,847

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
    • 109 Secor Rd, Chestertown, MD 21620
      109 Secor Rd, Chestertown, MD 21620
      109 Secor Rd, Chestertown, MD 21620
      /41

      Est $384,137

      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

      • $247/SF
      • 69 Days On Market
      • Last Sold Price $385,000
      • Apr 04, 2025

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

  • 8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    8706 Elm Rd, Chestertown, MD 21620
    /7

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    8706 Elm Rd, Chestertown, MD 21620

    Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the

    Andrew Meikle Doug Ashley Realtors, LLC

    8706 Elm Rd, Chestertown, MD 21620
  • 129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, MD 21620
    129 Parma Rd, Chestertown, 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 $325,017

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma 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 $405,697

      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

      • 10% Above List Price
      • $177/SF
      • 120 Days On Market
      • Last Sold Price $370,247
      • Nov 15, 2024

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • 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

    $3K PRICE DROP Under Contract
    • Land
    • 14,810 Sq Ft
    • $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
  • 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

    Current Estimated Value $711,365

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • 124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      /18

      Est $303,798

      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

      • 5% Above List Price
      • $275/SF
      • 9 Days On Market
      • Last Sold Price $290,000
      • Jul 03, 2024

      Last Listing Agent Jeff Guthrie Taylor Properties

  • 228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    228 Merganser Dr, Chestertown, MD 21620
    /13

    $99,000

    • Land
    • 22,215 Sq Ft
    • $194,118 per Acre

    228 Merganser Dr, Chestertown, MD 21620

    Situated on a quiet road, this half-acre property offers a great opportunity to enjoy the Eastern Shore lifestyle. Community water access to the Chester River is located at the end of the road and includes a boat ramp, making it easy to enjoy boating, fishing, crabbing, or paddle boarding right nearby. Located within the Queen Anne’s County school district and just minutes from downtown

    Mae Nordhoff Benson & Mangold, LLC

    228 Merganser Dr, Chestertown, MD 21620
  • 144 Char Nor Manor Blvd, Chestertown, MD 21620
    144 Char Nor Manor Blvd, Chestertown, MD 21620
    144 Char Nor Manor Blvd, 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 $72,010

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    144 Char Nor Manor Blvd, Chestertown, MD 21620
    • 317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      /33

      Est $668,642

      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% Below List Price
      • $273/SF
      • 0 Days On Market
      • Last Sold Price $685,000
      • Mar 07, 2025

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $25,000

    • Land
    • 39,204 Sq Ft
    • $27,778 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
  • 0 Elm Rd, Chestertown, MD 21620
    0 Elm Rd, 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
    • 201 Fairview Dr, Chestertown, MD 21620
      201 Fairview Dr, Chestertown, MD 21620
      201 Fairview Dr, Chestertown, MD 21620
      /22

      Est $324,832

      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

      • 2% Above List Price
      • $269/SF
      • 49 Days On Market
      • Last Sold Price $319,000
      • Mar 31, 2025

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /4

    $250,000

    • Land
    • 37,026 Sq Ft
    • $294,118 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 9925 Flatland Rd, Chestertown, MD 21620
    9925 Flatland 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 $180,339

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
    • 121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      /33

      Est $748,949

      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

      • $322/SF
      • 22 Days On Market
      • Last Sold Price $750,000
      • Jul 07, 2023

      Last Listing Agent Jennifer Gregorski Washington Fine Properties

  • 116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    116 N Cross St, Chestertown, MD 21620
    /9

    $109,999

    • Land
    • 7,840 Sq Ft
    • $611,106 per Acre

    116 N Cross St, Chestertown, MD 21620

    Great opportunity in the heart of Chestertown. This downtown commercial lot offers incredible potential just steps from established businesses and local amenities. Public sewer is available and accessible, making development that much more convenient. Positioned next to a professional office building, the property benefits from strong daily visibility with both foot and vehicle traffic passing

    Hayley Norris Select Land & Homes, LLC

    116 N Cross St, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, 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 $417,076

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • 204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      /12

      Est $841,444

      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

      • 16% Below List Price
      • $340/SF
      • 9 Days On Market
      • Last Sold Price $1,000,000
      • Jun 21, 2024

      Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

  • 23416 Cloquet Rd, Chestertown, MD 21620
    23416 Cloquet Rd, Chestertown, MD 21620
    23416 Cloquet Rd, Chestertown, MD 21620
    /34

    $384,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    23416 Cloquet Rd, Chestertown, MD 21620

    Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23416 Cloquet Rd, Chestertown, MD 21620
  • 108 Primrose Rd, Chestertown, MD 21620
    108 Primrose Rd, Chestertown, MD 21620
    108 Primrose 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 $389,219

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
    • 150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      /31

      Est $295,710

      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

      • 12% Above List Price
      • $251/SF
      • 5 Days On Market
      • Last Sold Price $265,000
      • Feb 09, 2024

      Last Listing Agent Kerry D'Azevedo Integrity Real Estate

  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    $22K PRICE INCREASE
    • Land
    • 14,810 Sq Ft
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 206 Flyway Ln, Chestertown, MD 21620
    206 Flyway 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 $498,739

    Last Listing Agent Kristin Lewis Integrity Real Estate

    206 Flyway Ln, Chestertown, MD 21620
    • 149 Longfellow Dr, Chestertown, MD 21620
      149 Longfellow Dr, Chestertown, MD 21620
      149 Longfellow Dr, Chestertown, MD 21620
      /25

      Est $401,877

      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

      • 4% Above List Price
      • $213/SF
      • 19 Days On Market
      • Last Sold Price $385,000
      • Apr 11, 2025

      Last Listing Agent Isaac Bahary KW Empower

  • 144 Prospect St, Chestertown, MD 21620
    144 Prospect St, Chestertown, MD 21620
    144 Prospect St, Chestertown, MD 21620
    /18

    $179,000

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft

    144 Prospect St, Chestertown, MD 21620

    Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county

    Michele Palmer Doug Ashley Realtors, LLC

    144 Prospect St, Chestertown, MD 21620
  • 7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck 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 $381,897

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • 123 Burchard Sawmill Rd, Chestertown, MD 21620
      123 Burchard Sawmill Rd, Chestertown, MD 21620
      123 Burchard Sawmill Rd, Chestertown, MD 21620
      /53

      Est $491,132

      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

      • 1% Above List Price
      • $294/SF
      • 4 Days On Market
      • Last Sold Price $485,000
      • May 01, 2025

      Last Listing Agent Crystal Pickett EXP Realty, LLC

  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /48

    $1,295,500

    Open Sun 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
  • 4671 Cliffs City Rd, Chestertown, MD 21620
    4671 Cliffs City Rd, Chestertown, MD 21620
    4671 Cliffs City Rd, 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 $804,829

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • 200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      /26

      Est $407,029

      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

      • 10% Above List Price
      • $251/SF
      • 4 Days On Market
      • Last Sold Price $370,000
      • Aug 07, 2023

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 22360 Great Oak Landing Rd, Chestertown, MD 21620
    22360 Great Oak Landing Rd, Chestertown, MD 21620
    22360 Great Oak Landing Rd, Chestertown, MD 21620
    /65

    $525,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft

    22360 Great Oak Landing Rd, Chestertown, MD 21620

    Nestled in the natural serene of Great Oak Estates, this beautiful 5 bedroom, 3.5 bathroom Nanticoke Home offers a flexible floor plan, updated kitchen, spacious backyard, and brand new Florida/Sun room, designed for both relaxation and entertaining. The heart of the home feautures a gourmet kitchen with granite counter tops, SS appliances, custom built ins, and connects to the family room with

    Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 18

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