Chestertown, MD Real Estate & Homes For Sale

51 homes

  • 529 Cannon St, Chestertown, MD 21620
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    NEWOPEN SAT, 11-1PM
    $385,000
    3bd
    2ba
    1,288 sqft
    529 Cannon St,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • Gateway Dr, Chestertown, MD 21620
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    NEW - 1 DAY AGO1.09 ACRES
    Cottage Street Realty LLC
  • 481 Pear Tree Point Rd, Chestertown, MD 21620
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    NEW - 2 DAYS AGONEW CONSTRUCTION0.39 ACRES
    $419,900
    3bd
    3ba
    1,512 sqft (on 0.39 acres)
    481 Pear Tree Point Rd,
    Chestertown, MD 21620
    Cross Street Realtors LLC
  • 240 Round Top Landing Rd, Chestertown, MD 21620
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    OPEN WED, 10-12PMCOMING SOON 4/39.58 ACRES
    $3,995,000
    3bd
    4ba
    4,804 sqft (on 9.58 acres)
    240 Round Top Landing Rd,
    Chestertown, MD 21620
    TTR Sotheby's International Realty
  • 22956 Fairgale Farm Ln, Chestertown, MD 21620
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    3.95 ACRES
    $1,525,000
    5bd
    5ba
    6,459 sqft (on 3.95 acres)
    22956 Fairgale Farm Ln,
    Chestertown, MD 21620
    Doug Ashley Realtors, LLC
  • 9062 Fairlee Rd, Chestertown, MD 21620
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    3.47 ACRES
    $385,500
    3bd
    2ba
    1,344 sqft (on 3.47 acres)
    9062 Fairlee Rd,
    Chestertown, MD 21620
    Taylor Properties
  • 10605 Tonopah Rd, Chestertown, MD 21620
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    0.46 ACRES
    $299,900
    4bd
    2ba
    1,248 sqft (on 0.46 acres)
    10605 Tonopah Rd,
    Chestertown, MD 21620
    RE/MAX Executive
  • 9816 Fairlee Rd, Chestertown, MD 21620
    OPEN SAT, 10-1PM6.29 ACRES
    $520,000
    3bd
    3ba
    1,624 sqft (on 6.29 acres)
    9816 Fairlee Rd,
    Chestertown, MD 21620
    RE/MAX Executive
  • 23315 Sandpiper Rd, Chestertown, MD 21620
    OPEN SAT, 11-2PMCOMING SOON 3/300.34 ACRES
    $259,000
    2bd
    1ba
    1,272 sqft (on 0.34 acres)
    23315 Sandpiper Rd,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • 118 Westwood Ln, Chestertown, MD 21620
    OPEN SAT, 1-3PM15 ACRES
    $649,900
    3bd
    2ba
    2,248 sqft (on 15 acres)
    118 Westwood Ln,
    Chestertown, MD 21620
    Berkshire Hathaway Homeservice Homesale Realty
  • 332 Truslow Rd, Chestertown, MD 21620
    0.69 ACRES
    $299,900
    2bd
    1ba
    1,408 sqft (on 0.69 acres)
    332 Truslow Rd,
    Chestertown, MD 21620
    Blackwell Real Estate, LLC
  • CLOQUET Rd, Chestertown, MD 21620
    1.51 ACRES
    Berkshire Hathaway HomeServices Homesale Realty
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    Taylor Properties
  • 210 Truslow Farm Ln, Chestertown, MD 21620
    3.23 ACRES
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #2, Chestertown, MD 21620
    2.3 ACRES
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #4, Chestertown, MD 21620
    3.16 ACRES
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #3, Chestertown, MD 21620
    3 ACRES
    Chesapeake Real Estate Associates, LLC
  • Map 36 Watertower Rd #80, Chestertown, MD 21620
    0.7 ACRES
    Doug Ashley Realtors, LLC
  • 8757 Orchard Dr, Chestertown, MD 21620
    1.89 ACRES
    $540,000
    3bd
    3ba
    2,210 sqft (on 1.89 acres)
    8757 Orchard Dr,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • 707 Round Top Rd, Chestertown, MD 21620
    0.69 ACRES
    $340,000
    3bd
    2ba
    1,296 sqft (on 0.69 acres)
    707 Round Top Rd,
    Chestertown, MD 21620
    The Hogans Agency Inc.
  • 24 & 25 Buck Neck Rd, Chestertown, MD 21620
    0.42 ACRES
    Doug Ashley Realtors, LLC
  • Millbrook Dr, Chestertown, MD 21620
    1.08 ACRES
    Chesapeake Real Estate Associates, LLC
  • 209 Myers Rd, Chestertown, MD 21620
    1.23 ACRES
    $415,000
    3bd
    2ba
    1,846 sqft (on 1.23 acres)
    209 Myers Rd,
    Chestertown, MD 21620
    Cross Street Realtors LLC
  • 23690 L Rd, Chestertown, MD 21620
    0.63 ACRES
    Keller Williams Flagship of Maryland
  • 9020 Cumberland St, Chestertown, MD 21620
    0.46 ACRES
    $297,000
    2bd
    2ba
    1,150 sqft (on 0.46 acres)
    9020 Cumberland St,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • Montgomery Ave, Chestertown, MD 21620
    The Hogans Agency Inc.
  • 870 Washington Ave, Chestertown, MD 21620
    Cross Street Realtors LLC
  • 106 Water 1/2 St   N, Chestertown, MD 21620
    Cross Street Realtors LLC
  • 22900 Handy Point Rd, Chestertown, MD 21620
    3.13 ACRES
    $1,765,000
    5bd
    5ba
    4,885 sqft (on 3.13 acres)
    22900 Handy Point Rd,
    Chestertown, MD 21620
    Davis Real Estate, Inc.
  • 147 Char Nor Manor Blvd, Chestertown, MD 21620
    0.52 ACRES
    Keller Williams Real Estate - Media
  • Lots 253 254 Carimon Rd, Chestertown, MD 21620
    0.34 ACRES
    Doug Ashley Realtors, LLC
  • Redfield Rd, Chestertown, MD 21620
    0.34 ACRES
    Long & Foster Real Estate, Inc.
  • Fish hatchery Rd, Chestertown, MD 21620
    0.34 ACRES
    Long & Foster Real Estate, Inc.
  • SPINNAKER Rd, Chestertown, MD 21620
    0.56 ACRES
    Long & Foster Real Estate, Inc.
  • 23710 L Rd, Chestertown, MD 21620
    0.5 ACRES
    Long & Foster Real Estate, Inc.
  • 23693 L Rd, Chestertown, MD 21620
    2 ACRES
    Long & Foster Real Estate, Inc.
  • 201 N  Water St, Chestertown, MD 21620
    0.39 ACRES
    $1,725,000
    4bd
    5ba
    5,195 sqft (on 0.39 acres)
    201 N Water St,
    Chestertown, MD 21620
    Maryland Heritage Properties
  • Landing Ln   #37, Chestertown, MD 21620
    NEW CONSTRUCTION
    Benson & Mangold, LLC
  • Flatland Rd, Chestertown, MD 21620
    87 ACRES
    The Land Group
  • Landing Ln   #25, Chestertown, MD 21620
    NEW CONSTRUCTION
    Benson & Mangold, LLC

Chestertown, MD Real Estate Trends

Learn about the Chestertown, MD housing market through trends and averages.

Affordability of Living in Chestertown, MD

The median home value is $345,467
MonthMedian home value
March 2023$327k
April 2023$328k
May 2023$331k
June 2023$334k
July 2023$336k
August 2023$338k
September 2023$339k
October 2023$340k
November 2023$342k
December 2023$343k
January 2024$344k
February 2024$345k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Chestertown, MD, by Home Size

Currently, there are 6 new listings and 51 homes for sale in Chestertown.
Home SizeHome Value*
2 bedrooms (4 homes)$265,438
3 bedrooms (16 homes)$322,198
4 bedrooms (4 homes)$442,055
*Home value over the past month

What Locals Say about Chestertown

  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
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  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
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  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
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  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
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  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
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  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
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  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
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  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
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  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
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