6,817

Chestertown, MD Homes

Section Image
  • /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 $402,578

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
    • /41

      Est $333,631

      Not Listed For Sale

      6744 Church Hill Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,298 Sq Ft
      • Built 1964
      6744 Church Hill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 199 Days On Market

      Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

  • /2

    $200,000

    Coming Soon Sep 21
    • 4 Beds
    • 1 Bath
    • 1,816 Sq Ft

    223 Mount Vernon Ave, Chestertown, MD 21620

    Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront.Currently occupied,

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    223 Mount Vernon Ave, 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 $801,589

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
    • /26

      Est $448,147

      Not Listed For Sale

      209 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft
      • Built 2001
      209 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

  • /30

    $300,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    104 Lincoln Dr, Chestertown, MD 21620

    This adorable rancher combines a fresh, updated interior with plenty of outdoor space to enjoy. Come step inside to a bright and welcoming home filled with natural light, LVP flooring and a modern, neutral color palette that flows throughout. The crisp white kitchen keeps things light and timeless, while the spacious living room offers plenty of room to relax, gather and make the space your own.

    Crystal Smith RE/MAX Executive

    104 Lincoln Dr, 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 $375,249

    Last Listing Agent Joie White Northrop Realty

    136 Hilltop Dr, Chestertown, MD 21620
    • /21

      Est $345,062

      Not Listed For Sale

      112 Pine Chip Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1978
      112 Pine Chip Rd, Chestertown, MD 21620

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • /7

    $225,000

    • Land
    • 37,897 Sq Ft
    • $258,621 per Acre

    3 Haacke Dr, Chestertown, MD 21620

    This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± 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

    Hayley Norris Select Land & Homes, LLC

    3 Haacke Dr, 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 $509,121

    Last Listing Agent Lauren Matera LPT Realty, LLC

    100 Adela Way, Chestertown, MD 21620
    • /60

      Est $585,285

      Not Listed For Sale

      1316 Ewingtown Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,476 Sq Ft
      • Built 2002
      1316 Ewingtown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Travis Gray Engel & Völkers Annapolis

  • /3

    $3,000

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

    0 Lenapah Rd, Chestertown, MD 21620

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:30 AM. 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

    Adam Shpritz Ashland Auction Group LLC

    0 Lenapah Rd, 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 $260,184

    Last Listing Agent Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
    • /24

      Est $316,026

      Not Listed For Sale

      2607 Mcginnes Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft
      • Built 1978
      2607 Mcginnes Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /68

    $799,000

    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, 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 $878,399

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • /23

      Est $298,965

      Not Listed For Sale

      208 Central Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1978
      208 Central Dr, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /61

    $649,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 3 Baths
    • 2,864 Sq Ft

    22400 Great Oak Landing Rd, Chestertown, MD 21620

    Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    22400 Great Oak Landing 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 $398,940

    Last Listing Agent Lauren Matera LPT Realty, LLC

    128 Edmore Rd, Chestertown, MD 21620
    • /33

      Est $275,857

      Not Listed For Sale

      114 Darden Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1978
      114 Darden Rd, Chestertown, MD 21620

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Lee Wolff FSBO Broker

  • /53

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, 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 Mrs. Terri E Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
    • /48

      Est $568,714

      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

      • 52 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /50

    $339,000

    $106K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck 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 $376,808

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    104 Iris Rd, Chestertown, MD 21620
    • /22

      Est $207,249

      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

      • 14 Days On Market

      Last Listing Agent Leigh Lawson Metro Bay Realty

  • /2

    $40,000

    • Land
    • 4,791 Sq Ft
    • $363,636 per Acre

    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620

    Vaughn Hogans The Hogans Agency

    0 Montgomery Unit MDKE2003418, 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 $291,904

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
    • /24

      Est $332,423

      Not Listed For Sale

      109 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1993
      109 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • /2

    $10,000

    $5K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $29,412 per Acre

    0 Sheldrake Dr, Chestertown, MD 21620

    Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    0 Sheldrake Dr, Chestertown, MD 21620
  • /36

    $270,000

    Sold Feb 19, 2026

    24339 Chestertown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1964

    Last Sold Summary

    • $281/SF
    • 4 Days On Market

    Current Estimated Value $266,107

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    24339 Chestertown Rd, Chestertown, MD 21620
    • /25

      Est $476,910

      Not Listed For Sale

      130 Sheaffer Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,766 Sq Ft
      • Built 1999
      130 Sheaffer Rd, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Biana Arentz Coldwell Banker Realty

  • /46

    $629,900

    Pending
    • 3 Beds
    • 2 Baths
    • 2,430 Sq Ft

    201 River Rd, Chestertown, MD 21620

    Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 River Rd, Chestertown, MD 21620
  • /2

    $3,000,000

    Sold Aug 14, 2026

    25440 Learman Rd, Chestertown, MD 21620

    • 3 Beds
    • 4 Baths
    • 3,142 Sq Ft
    • Built 1955

    Last Sold Summary

    • $955/SF
    • 14 Days On Market

    Current Estimated Value $2,159,136

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    25440 Learman Rd, Chestertown, MD 21620
    • /26

      Est $335,136

      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

      • 25 Days On Market

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • /34

    $440,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 1,058 Sq Ft

    104 Church Aly, Chestertown, MD 21620

    A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Church Aly, Chestertown, MD 21620
  • /2

    $332,000

    Sold Apr 10, 2026

    23055 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 1948

    Last Sold Summary

    • 1% Above List Price
    • $204/SF
    • 5 Days On Market

    Current Estimated Value $326,724

    Last Listing Agent Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
    • /24

      Est $596,877

      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

      • 16 Days On Market

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • /36

    $345,000

    • 3 Beds
    • 1.5 Baths
    • 1,398 Sq Ft

    217 Edmore Rd, Chestertown, MD 21620

    Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then.Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings.

    Michele Palmer Doug Ashley Realtors, LLC

    217 Edmore Rd, Chestertown, MD 21620
  • /47

    $330,000

    Sold Sep 14, 2026

    8312 Broad Neck Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 3,292 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Below List Price
    • $100/SF
    • 14 Days On Market

    Current Estimated Value $419,018

    Last Listing Agent Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, Chestertown, MD 21620

Showing Results 201 - 240, Page 6 of 18

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