6,890

Chestertown, MD Homes

Section Image
    • /16

      Est $366,636

      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

  • /29

    $229,990

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    24581 Willow Oak Ln, Chestertown, MD 21620

    If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

    Michele Palmer Doug Ashley Realtors, LLC

    24581 Willow Oak Ln, Chestertown, MD 21620
  • /70

    $620,000

    Sold Apr 20, 2026

    11040 Kylie Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft
    • Built 2000

    Last Sold Summary

    • $168/SF
    • 497 Days On Market

    Current Estimated Value $632,958

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
    • /80

      Est $622,297

      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

  • /70

    $499,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /12

    $162,000

    Sold Nov 10, 2025

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620

    • Land
    • 5.34 Acres
    • $30,337 per Acre

    Last Sold Summary

    • 64 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    • /28

      Est $438,533

      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

  • /92

    $829,000

    $36K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic DistrictThe Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • /73

    $435,000

    Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Current Estimated Value $445,020

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • /43

      Est $393,695

      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

  • /55

    $365,000

    $60K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    240 Merganser Dr, Chestertown, MD 21620

    Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting.Enjoy easy access to

    Erin Anderson Chesapeake Real Estate Associates, LLC

    240 Merganser Dr, Chestertown, MD 21620
  • /32

    $415,000

    Sold Jan 07, 2026

    411 Greenwood Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft
    • Built 2003

    Last Sold Summary

    • $248/SF
    • 1 Day On Market

    Current Estimated Value $420,501

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
    • /30

      Est $425,729

      Not Listed For Sale

      2771 Mcginnes Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,714 Sq Ft
      • Built 1999
      2771 Mcginnes Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • /74

    $824,900

    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • /36

    $750,000

    Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
    • /6

      Est $684,956

      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

  • /11

    $265,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,967 Sq Ft

    1904 Pondtown Rd, Chestertown, MD 21620

    Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and privacy of a rural setting while still being conveniently located near Chestertown, Millington, and major commuter routes. The spacious lot provides room for gardening, recreation, hobbies, or simply enjoying the outdoors.

    Lonnie Gilmore Keller Williams Flagship

    1904 Pondtown Rd, Chestertown, MD 21620
  • /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,347,184

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • /19

      Not Listed For Sale

      131 E Step Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1991
      131 E Step Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • /39

    $380,000

    • 4 Beds
    • 2 Baths
    • 1,277 Sq Ft

    213 Byford Dr, Chestertown, MD 21620

    Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other

    Grace Crockett Doug Ashley Realtors, LLC

    213 Byford Dr, Chestertown, MD 21620
  • /24

    $455,000

    Sold Oct 21, 2025

    224 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1978

    Last Sold Summary

    • $241/SF
    • 13 Days On Market

    Current Estimated Value $456,495

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
    • /5

      Est $642,675

      Not Listed For Sale

      193 Westwood Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 3,572 Sq Ft
      • Built 1974
      193 Westwood Ln, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • /7

    $5,000

    • Land
    • 16,117 Sq Ft
    • $13,514 per Acre

    0 Fish Hatchery Rd Unit MDKE2004754, 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, 12:35 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 all the attractions in Chestertown, Maryland. It offers easy

    Adam Shpritz Ashland Auction Group LLC

    0 Fish Hatchery Rd Unit MDKE2004754, Chestertown, MD 21620
  • /31

    $250,000

    Sold Nov 11, 2025

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1967

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $259,115

    Last Listing Agent Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
    • /8

      Est $186,077

      Not Listed For Sale

      1814 Pondtown Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 973 Sq Ft
      • Built 1974
      1814 Pondtown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

  • /9

    $155,000

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    409 Calvert St, Chestertown, MD 21620

    Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    409 Calvert St, Chestertown, MD 21620
  • /45

    $310,000

    Sold Aug 15, 2025

    24095 Chestertown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1972

    Last Sold Summary

    • $281/SF
    • 87 Days On Market

    Current Estimated Value $297,416

    Last Listing Agent Lona Todd Taylor Properties

    24095 Chestertown Rd, Chestertown, MD 21620
    • /23

      Not Listed For Sale

      107 Char Nor Manor Blvd, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 2,128 Sq Ft
      • Built 1999
      107 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 56 Days On Market

  • /3

    $85,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • /36

    $355,000

    Sold Aug 12, 2025

    114 Ryan Ct, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Built 1978

    Last Sold Summary

    • $237/SF
    • 83 Days On Market

    Current Estimated Value $375,539

    Last Listing Agent Julie Santoboni Taylor Properties

    114 Ryan Ct, Chestertown, MD 21620
    • /34

      Est $280,724

      Not Listed For Sale

      118 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,114 Sq Ft
      • Built 1965
      118 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 120 Days On Market

  • /2

    $9,000

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

    0 Buck Neck Rd Unit MDKE2005262, 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 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620
  • /19

    $354,900

    Sold Nov 10, 2025

    2010 Mcginnes Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,253 Sq Ft
    • Built 1962

    Last Sold Summary

    • $283/SF
    • 14 Days On Market

    Current Estimated Value $351,074

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
    • /24

      Est $248,473

      Not Listed For Sale

      235 Burchard Sawmill Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1930
      235 Burchard Sawmill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 115 Days On Market

  • /3

    $750,000

    $45K PRICE DROP
    • Land
    • 4,356 Sq Ft
    • $7,500,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /29

    $359,900

    Sold Nov 24, 2025

    221 Old Bridge Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • Built 1924

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $364,289

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
    • /8

      Est $382,144

      Not Listed For Sale

      101 Char Nor Manor Blvd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,156 Sq Ft
      • Built 1965
      101 Char Nor Manor Blvd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, 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 2A, Chestertown, MD 21620
  • /30

    $1,100,000

    Sold Jan 16, 2026

    300 Hickory Ln, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 1940

    Last Sold Summary

    • $302/SF
    • 163 Days On Market

    Current Estimated Value $1,128,715

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
    • /17

      Est $269,610

      Not Listed For Sale

      305 Pine Tree Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 826 Sq Ft
      • Built 1961
      305 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 298 Days On Market

Showing Results 281 - 320, Page 8 of 18

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