6,817

Chestertown, MD Homes

Section Image
    • /37

      Est $650,332

      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

      • 1 Day On Market

      Last Listing Agent Michelle Schwab Krauss Real Property Brokerage

  • /2

    $24,000

    $4K PRICE INCREASE
    • Land
    • 21,780 Sq Ft
    • $48,000 per Acre

    23710 L Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    23710 L Rd, Chestertown, MD 21620
  • /29

    $330,000

    Sold Apr 03, 2026

    23110 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft
    • Built 1938

    Last Sold Summary

    • $183/SF
    • 174 Days On Market

    Current Estimated Value $321,904

    Last Listing Agent Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • /87

      Est $412,785

      Not Listed For Sale

      312 Princess Anne Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 1,848 Sq Ft
      • Built 1987
      312 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

  • /52

    $750,000

    • 3 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    216 Birch Run Rd, Chestertown, MD 21620

    Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A

    Liddy Campbell TTR Sotheby's International Realty

    216 Birch Run Rd, Chestertown, MD 21620
  • /6

    $5,000

    Sold Jan 08, 2026

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    • Land
    • 18,295 Sq Ft
    • $11,905 per Acre

    Last Sold Summary

    • 230 Days On Market

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    • /80

      Est $407,394

      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

      • 35 Days On Market

      Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

  • /26

    $340,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,972 Sq Ft

    214 Silver Heel Rd, Chestertown, MD 21620

    Price Reduction! VERY motivated seller—open to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer construction—major

    Chris Kendall Cross Street Realtors LLC

    214 Silver Heel Rd, Chestertown, MD 21620
  • /47

    $355,000

    Sold May 26, 2026

    349 & 351 High St, Chestertown, MD 21620

    • Studio
    • 3,664 Sq Ft
    • Built 1900

    Last Sold Summary

    • $97/SF
    • 496 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
    • /48

      Est $391,560

      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

      • 50 Days On Market

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /25

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • /25

    $334,000

    Sold Apr 06, 2026

    8750 Georgetown Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2014

    Last Sold Summary

    • $176/SF
    • 134 Days On Market

    Current Estimated Value $345,868

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
    • /42

      Est $399,295

      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

      • 39 Days On Market

      Last Listing Agent Stacey Stracke Douglas Realty, LLC

  • /50

    $448,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 3,262 Sq Ft

    25750 Collins Ave, Chestertown, MD 21620

    Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile.

    Grace Crockett Doug Ashley Realtors, LLC

    25750 Collins Ave, Chestertown, MD 21620
  • /49

    $552,000

    Sold Apr 17, 2026

    216 Blakefield Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $230/SF
    • 94 Days On Market

    Current Estimated Value $553,966

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
    • /57

      Est $535,025

      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

      • 41 Days On Market

      Last Listing Agent Chardae Eduruke Real Broker LLC

  • /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /15

    $555,000

    Sold Jan 12, 2026

    26933 Mallard Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1956

    Last Sold Summary

    • $347/SF
    • 77 Days On Market

    Current Estimated Value $569,669

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
    • /62

      Est $397,210

      Not Listed For Sale

      216 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1986
      216 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Brett Schrader Taylor Properties

  • /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • /31

    $310,000

    Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $314,902

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
    • /8

      Est $1,185,008

      Not Listed For Sale

      545 Fey Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,420 Sq Ft
      • Built 1948
      545 Fey Rd, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /2

    $38,000

    $17K PRICE INCREASE
    • Land
    • 24,393 Sq Ft
    • $67,857 per Acre

    0 Spinnaker Rd, Chestertown, MD 21620

    Dee Dee Miller Paul Wesley Real Estate

    0 Spinnaker Rd, Chestertown, MD 21620
  • /72

    $1,200,000

    Sold Aug 14, 2026

    202 Royston Shores Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 1968

    Last Sold Summary

    • $524/SF
    • 16 Days On Market

    Current Estimated Value $1,175,998

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    202 Royston Shores Rd, Chestertown, MD 21620
    • /18

      Est $329,276

      Not Listed For Sale

      120 Edmore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1986
      120 Edmore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

  • /26

    $786,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 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

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • /18

    $620,000

    Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Current Estimated Value $636,337

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
    • /16

      Est $344,564

      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

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /18

    $275,000

    Under Contract
    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • /41

    $740,000

    Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Current Estimated Value $759,066

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
    • /80

      Est $586,771

      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

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • /2

    $40,000

    Under Contract
    • Land
    • 14,810 Sq Ft
    • $117,647 per Acre

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620

    Lots 287 and 288 on Tonopah Rd. in Chestertown. 15,000 sq/ft, .344 acres. Approved perc site on file. The HO Association is voluntary. For an annual fee of $40 water access is offered to the boat ramp and Worton Creek. Marina and Boat slips are available through application for an extra fee. Check with Listing Agent for more information about the community.

    Jo Ann Edwards The Hogans Agency

    0 Tonopah Rd Unit MDKE2005564, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $357,407

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
    • /28

      Est $433,705

      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

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /17

    $259,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,420 Sq Ft

    249 Island Lark Way, Chestertown, MD 21620

    Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction.Conveniently located with an easy commute to Route 301 and just around the corner from the

    Casey Scattergood Cross Street Realtors LLC

    249 Island Lark Way, Chestertown, MD 21620
  • /40

    $293,000

    Sold Jun 08, 2026

    301 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 54 Days On Market

    Current Estimated Value $293,876

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
    • /43

      Est $393,040

      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

      Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

  • /19

    $3,000,000

    Pending
    • Land
    • 87.34 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community.

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, Chestertown, MD 21620
  • /2

    $339,900

    Sold Apr 21, 2026

    103 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2023

    Last Sold Summary

    • $197/SF
    • 0 Days On Market

    Current Estimated Value $339,854

    Last Listing Agent Laura Snyder American Premier Realty, LLC

    103 Flying Cloud Dr, Chestertown, MD 21620
    • /6

      Est $726,868

      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

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home