6,952

Homes in ZIP Code 21620

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  • /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 $450,145

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
    • /35

      Est $416,654

      Not Listed For Sale

      313 River Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,080 Sq Ft
      • Built 1964
      313 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /32

    $304,000

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

    7464 Shortall St, Chestertown, MD 21620

    Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy.The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    7464 Shortall St, 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 $422,072

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
    • /28

      Est $282,363

      Not Listed For Sale

      124 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1974
      124 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /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

    $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
    • /32

      Est $340,154

      Not Listed For Sale

      729 Rosin Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      729 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /2

    $5,000

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

    0 Buck Neck Rd Unit MDKE2005262, Chestertown, MD 21620

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

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Buck Neck Rd Unit MDKE2005262, 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 $1,330,551

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
    • /50

      Est $345,256

      Not Listed For Sale

      201 Tamarack Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,225 Sq Ft
      • Built 1973
      201 Tamarack Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Petra Quinn Realty Navigator

  • /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
  • /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 $466,142

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
    • /29

      Est $317,640

      Not Listed For Sale

      332 Truslow Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,408 Sq Ft
      • Built 1900
      332 Truslow Rd, Chestertown, MD 21620

      Last Sold Summary

      • 118 Days On Market

      Last Listing Agent James Blackwell Blackwell Real Estate, LLC

  • /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
  • /28

    $289,000

    Sold Aug 21, 2026

    517 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 17% Below List Price
    • $232/SF
    • 41 Days On Market

    Current Estimated Value $307,743

    Last Listing Agent Barry Hess Keller Williams Flagship

    517 Round Top Rd, Chestertown, MD 21620
    • /31

      Est $339,467

      Not Listed For Sale

      707 Round Top Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1976
      707 Round Top Rd, Chestertown, MD 21620

      Last Sold Summary

      • 75 Days On Market

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, 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 $259,514

    Last Listing Agent Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
    • /21

      Est $301,386

      Not Listed For Sale

      212 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1972
      212 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    117 N Water St Unit 1A, 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 1A, Chestertown, MD 21620
  • /8

    $75,000

    Sold Aug 13, 2026

    0 East St, Chestertown, MD 21620

    • Land
    • 20,908 Sq Ft
    • $156,250 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620
    • /25

      Est $341,545

      Not Listed For Sale

      324 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,360 Sq Ft
      • Built 1988
      324 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Christopher Carr HomeZu

  • /49

    $475,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft

    105 N Water St Unit 2, Chestertown, MD 21620

    Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condominium offers an exceptional opportunity to enjoy life along the banks of the Chester River. Set within an architecturally significant 1800s building that reflects the timeless character of this remarkable town, the residence

    Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, 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 $360,363

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
    • /26

      Est $246,988

      Not Listed For Sale

      118 Tuxedo Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      118 Tuxedo Rd, Chestertown, MD 21620

      Last Sold Summary

      • 121 Days On Market

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, 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
    • /22

      Est $195,846

      Not Listed For Sale

      110 Philosophers Terrace, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 896 Sq Ft
      • Built 1955
      110 Philosophers Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • /23

    $200,000

    • Land
    • 5.81 Acres
    • $34,423 per Acre

    0 Round Top Rd, Chestertown, MD 21620

    This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    0 Round Top Rd, 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 $1,129,907

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
    • /58

      Est $850,804

      Not Listed For Sale

      105 S Water St, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,565 Sq Ft
      • Built 1900
      105 S Water St, Chestertown, MD 21620

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Richard Keaveney Cross Street Realtors LLC

  • /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • /2

    $1,650,000

    Sold Jun 30, 2026

    114 Chester View, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $799/SF
    • 0 Days On Market

    Current Estimated Value $1,177,591

    Last Listing Agent Jack Boniface Cross Street Realtors LLC

    114 Chester View, Chestertown, MD 21620
    • /39

      Est $263,794

      Not Listed For Sale

      114 School Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,102 Sq Ft
      • Built 1966
      114 School Rd, Chestertown, MD 21620

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • /65

    $455,000

    Sold Apr 13, 2026

    206 Camelot Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft
    • Built 2009

    Last Sold Summary

    • 13% Below List Price
    • $208/SF
    • 30 Days On Market

    Current Estimated Value $464,468

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
    • /36

      Est $400,308

      Not Listed For Sale

      23118 Raleigh Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,625 Sq Ft
      • Built 1970
      23118 Raleigh Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /40

    $275,000

    • 3 Beds
    • 1 Bath
    • 975 Sq Ft

    7482 Poplar Ave, Chestertown, MD 21620

    Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite

    Lona Todd Taylor Properties

    7482 Poplar Ave, Chestertown, MD 21620
  • /43

    $379,900

    Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $391,610

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620

Showing Results 321 - 360, Page 9 of 18

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