6,886

Chestertown, MD Homes

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  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /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
  • 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 $373,075

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • 112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      /48

      Est $520,717 Not Listed For Sale

      112 Sheaffer Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,864 Sq Ft
      • Built 1989
      112 Sheaffer Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $170/SF
      • 52 Days On Market

      Last Sold Price $486,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    109 Wilton Rd, Chestertown, MD 21620
    /31

    $344,900

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    109 Wilton Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Wilton Rd, 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 $891,576

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • 224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      224 Fey Rd, Chestertown, MD 21620
      /25

      Est $388,096 Not Listed For Sale

      224 Fey Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,504 Sq Ft
      • Built 1988
      224 Fey Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1% Above List Price
      • $256/SF
      • 1 Day On Market

      Last Sold Price $385,000

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • 23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    23043 Bay Shore Spur, Chestertown, MD 21620
    /27

    $325,000 Under Contract

    • 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
  • 249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    /28

    $343,600 Sold Mar 26, 2025

    249 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft
    • Built 2000

    Last Sold Summary

    • $221/SF
    • 14 Days On Market

    Current Estimated Value $355,250

    Last Listing Agent Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
    • 340 Pine Tree Rd, Chestertown, MD 21620
      340 Pine Tree Rd, Chestertown, MD 21620
      340 Pine Tree Rd, Chestertown, MD 21620
      /22

      Est $206,974 Not Listed For Sale

      340 Pine Tree Rd, Chestertown, MD 21620

      • Studio
      • 1,080 Sq Ft
      • Built 1920
      340 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $162/SF
      • 14 Days On Market

      Last Sold Price $175,000

      Last Listing Agent Leigh Lawson Metro Bay Realty

  • 23055 Old Fairlee Rd, Chestertown, MD 21620
    23055 Old Fairlee Rd, Chestertown, MD 21620
    23055 Old Fairlee Rd, Chestertown, MD 21620
    /26

    $330,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft

    23055 Old Fairlee Rd, Chestertown, MD 21620

    OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!!Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a 1⁄2-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank

    Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $75,000 Sold Dec 08, 2025

    109 2nd St, Chestertown, MD 21620

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 49 Days On Market

    Current Estimated Value $84,667

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
    • 206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      206 Tamarack Rd, Chestertown, MD 21620
      /16

      Est $378,205 Not Listed For Sale

      206 Tamarack Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1973
      206 Tamarack Rd, Chestertown, MD 21620

      Last Sold Summary

      • 19% Above List Price
      • $203/SF
      • 8 Days On Market

      Last Sold Price $317,000

      Last Listing Agent Alyson Anderson Allfirst Realty, Inc.

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

    $15,000

    • Land
    • 0.52 Acre
    • $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
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, 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 $872,785

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • 118 Hilltop Dr, Chestertown, MD 21620
      118 Hilltop Dr, Chestertown, MD 21620
      118 Hilltop Dr, Chestertown, MD 21620
      /28

      Est $490,857 Not Listed For Sale

      118 Hilltop Dr, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,188 Sq Ft
      • Built 2000
      118 Hilltop Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $197/SF
      • 3 Days On Market

      Last Sold Price $430,000

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /29

    $339,900 Pending

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace

    Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    /2

    $30,000 Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 0.83 Acre
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    • 228 Concord Rd, Chestertown, MD 21620
      228 Concord Rd, Chestertown, MD 21620
      228 Concord Rd, Chestertown, MD 21620
      /26

      Est $338,930 Not Listed For Sale

      228 Concord Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1974
      228 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $217/SF
      • 25 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • 349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    /47

    $395,000 Under Contract

    • Studio
    • 3,664 Sq Ft

    349 & 351 High St, Chestertown, MD 21620

    A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character

    Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • 129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    /38

    $575,000 Sold Jun 06, 2025

    129 N Queen St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 19 Days On Market

    Current Estimated Value $598,782

    Last Listing Agent William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
    • 240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      240 Duke of Kent St, Chestertown, MD 21620
      /33

      Est $428,140 Not Listed For Sale

      240 Duke of Kent St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft
      • Built 1989
      240 Duke of Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $223/SF
      • 30 Days On Market

      Last Sold Price $399,900

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    /25

    $334,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    8750 Georgetown Rd, Chestertown, MD 21620

    Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $392,500 Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Current Estimated Value $393,638

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
    • 415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      415 Fairview Dr, Chestertown, MD 21620
      /24

      Est $530,108 Not Listed For Sale

      415 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft
      • Built 1973
      415 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 26% Below List Price
      • $522/SF
      • 16 Days On Market

      Last Sold Price $718,000

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • 0 Kinglet Rd, Chestertown, MD 21620
    0 Kinglet Rd, Chestertown, MD 21620
    /2

    $9,000

    • Land
    • 0.34 Acre
    • $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
  • 9048 Georgetown Rd, Chestertown, MD 21620
    9048 Georgetown Rd, Chestertown, MD 21620
    /2

    $45,000 Sold Mar 26, 2025

    9048 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 1.21 Acres
    • $37,190 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 713 Days On Market

    Current Estimated Value $48,284

    Last Listing Agent Beverly Sloane Benson & Mangold, LLC

    9048 Georgetown Rd, Chestertown, MD 21620
    • 319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      319 Fairview Dr, Chestertown, MD 21620
      /37

      Est $565,882 Not Listed For Sale

      319 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 2,128 Sq Ft
      • Built 1961
      319 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 16% Below List Price
      • $317/SF
      • 1 Day On Market

      Last Sold Price $675,000

      Last Listing Agent Michelle Schwab Krauss Real Property Brokerage

  • 216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    /49

    $559,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    216 Blakefield Dr, Chestertown, MD 21620

    The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $508,954 Sold Dec 04, 2025

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • $198/SF
    • 10 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
    • 221 River Rd, Chestertown, MD 21620
      221 River Rd, Chestertown, MD 21620
      221 River Rd, Chestertown, MD 21620
      /80

      Est $398,358 Not Listed For Sale

      221 River Rd, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1969
      221 River Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $172/SF
      • 35 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /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
  • 104 Iris Rd, Chestertown, MD 21620
    104 Iris Rd, Chestertown, MD 21620
    104 Iris Rd, Chestertown, MD 21620
    /36

    $379,000 Sold Jan 30, 2026

    104 Iris Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 2006

    Last Sold Summary

    • $223/SF
    • 11 Days On Market

    Current Estimated Value $375,146

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    104 Iris Rd, Chestertown, MD 21620
    • 125 Primrose Rd, Chestertown, MD 21620
      125 Primrose Rd, Chestertown, MD 21620
      125 Primrose Rd, Chestertown, MD 21620
      /48

      Est $357,897 Not Listed For Sale

      125 Primrose Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,102 Sq Ft
      • Built 1976
      125 Primrose Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $167/SF
      • 50 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • 301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    301 Lincoln Dr, Chestertown, MD 21620
    /3

    $309,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    301 Lincoln Dr, Chestertown, MD 21620

    Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining.The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is

    Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $312,000 Sold Jun 13, 2025

    306 Cedar St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1959

    Last Sold Summary

    • $222/SF
    • 55 Days On Market

    Current Estimated Value $326,362

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
    • 210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      210 Rosin Dr, Chestertown, MD 21620
      /42

      Est $405,813 Not Listed For Sale

      210 Rosin Dr, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 2,352 Sq Ft
      • Built 1987
      210 Rosin Dr, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $155/SF
      • 39 Days On Market

      Last Sold Price $365,000

      Last Listing Agent Stacey Stracke Douglas Realty, LLC

  • 117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    /23

    $350,000

    • 7 Beds
    • 6 Baths
    • 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
  • 107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    /27

    $290,000 Sold Jan 16, 2026

    107 Malone Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1962

    Last Sold Summary

    • $242/SF
    • 69 Days On Market

    Current Estimated Value $282,426

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
    • 126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      126 Hilltop Dr, Chestertown, MD 21620
      /57

      Est $498,864 Not Listed For Sale

      126 Hilltop Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,733 Sq Ft
      • Built 2001
      126 Hilltop Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $170/SF
      • 41 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Chardae Eduruke Taylor Properties

  • 3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    3 Haacke Dr, Chestertown, MD 21620
    /5

    $225,000 Pending

    • Land
    • 0.96 Acre
    • $234,375 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, Chestertown, MD 21620

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