Chestertown, MD Real Estate & Homes For Sale

63 homes

  • 21345 Persimmon Dr, Chestertown, MD 21620
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    $158,000
    2bd
    1ba
    1,232 sqft
    21345 Persimmon Dr,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • 122 1st St, Chestertown, MD 21620
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    NEWCOMING SOON 4/300.75 ACRES
    $150,000
    2bd
    1ba
    720 sqft (on 0.75 acres)
    122 1st St,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • 7755 Waterview Ln, Chestertown, MD 21620
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    0.61 ACRES
    $975,000
    4bd
    3ba
    4,730 sqft (on 0.61 acres)
    7755 Waterview Ln,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • 235 Burchard Sawmill Rd, Chestertown, MD 21620
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    0.5 ACRES
    $289,000
    2bd
    2ba
    864 sqft (on 0.50 acres)
    235 Burchard Sawmill Rd,
    Chestertown, MD 21620
    Village Real Estate Company LLC
  • 349 & 351 High St, Chestertown, MD 21620
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    $425,000
    6bd
    3,664 sqft
    349 & 351 High St,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • PARCEL Buck Neck Rd, Chestertown, MD 21620
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    AUCTION0.34 ACRES
    $15,000
    PARCEL Buck Neck Rd,
    Chestertown, MD 21620
    Ashland Auction Group LLC
  • Sandpiper Rd, Chestertown, MD 21620
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    AUCTION0.34 ACRES
    $15,000
    Sandpiper Rd,
    Chestertown, MD 21620
    Ashland Auction Group LLC
  • BUCK NECK Rd, Chestertown, MD 21620
    1 ACRE
    $12,500
    BUCK NECK Rd,
    Chestertown, MD 21620
    Select Land & Homes, LLC
  • 113 Pine Cove Ln, Chestertown, MD 21620
    0.45 ACRES
    $68,500
    113 Pine Cove Ln,
    Chestertown, MD 21620
    Select Land & Homes, LLC
  • 1521 Dudley Corners Rd, Millington, MD 21651
    1 ACRE
    $179,000
    3bd
    2ba
    1,032 sqft (on 1 acre)
    1521 Dudley Corners Rd,
    Millington, MD 21651
    HomeSmart
  • 128 N Queen St, Chestertown, MD 21620
    OPEN SAT, 11-2PMCOMING SOON 4/27
    $650,000
    5bd
    3,497 sqft
    128 N Queen St,
    Chestertown, MD 21620
    Coldwell Banker Chesapeake Real Estate Company
  • 117 N Water St #3B, Chestertown, MD 21620
    $385,000
    1bd
    1ba
    652 sqft
    117 N Water St #3B,
    Chestertown, MD 21620
    Gunther-McClary Real Estate
  • 117 N Water St #2A, Chestertown, MD 21620
    $415,000
    2bd
    1ba
    787 sqft
    117 N Water St #2A,
    Chestertown, MD 21620
    Gunther-McClary Real Estate
  • 117 N Water St #2B, Chestertown, MD 21620
    $405,000
    1bd
    1ba
    850 sqft
    117 N Water St #2B,
    Chestertown, MD 21620
    Gunther-McClary Real Estate
  • 117 N Water St #3A, Chestertown, MD 21620
    $395,000
    2bd
    1ba
    729 sqft
    117 N Water St #3A,
    Chestertown, MD 21620
    Gunther-McClary Real Estate
  • 8049 Quaker Neck Rd, Chestertown, MD 21620
    1.25 ACRES
    $848,000
    4bd
    2ba
    1,660 sqft (on 1.25 acres)
    8049 Quaker Neck Rd,
    Chestertown, MD 21620
    Gunther-McClary Real Estate
  • 310 Longfellow Dr, Chestertown, MD 21620
    0.34 ACRES
    $329,000
    3bd
    2ba
    1,560 sqft (on 0.34 acres)
    310 Longfellow Dr,
    Chestertown, MD 21620
    Berkshire Hathaway Homeservice Homesale Realty
  • 240 Round Top Landing Rd, Chestertown, MD 21620
    9.58 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
  • 481 Pear Tree Point Rd, Chestertown, MD 21620
    NEW 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
  • 22956 Fairgale Farm Ln, Chestertown, MD 21620
    3.95 ACRES
    $1,460,000
    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
    3.47 ACRES
    $365,000
    3bd
    2ba
    1,344 sqft (on 3.47 acres)
    9062 Fairlee Rd,
    Chestertown, MD 21620
    Taylor Properties
  • 118 Westwood Ln, Chestertown, MD 21620
    15 ACRES
    $625,000
    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
    $289,899
    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
    $70,000
    CLOQUET Rd,
    Chestertown, MD 21620
    Berkshire Hathaway HomeServices Homesale Realty
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    $449,000
    3bd
    1ba
    1,128 sqft
    134 Char Nor Manor Blvd,
    Chestertown, MD 21620
    Taylor Properties
  • 210 Truslow Farm Ln, Chestertown, MD 21620
    3.23 ACRES
    $425,000
    210 Truslow Farm Ln,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #2, Chestertown, MD 21620
    2.3 ACRES
    $519,900
    Truslow Farm Ln #2,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #4, Chestertown, MD 21620
    3.16 ACRES
    $519,900
    Truslow Farm Ln #4,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • Truslow Farm Ln #3, Chestertown, MD 21620
    3 ACRES
    $519,900
    Truslow Farm Ln #3,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • Map 36 Watertower Rd #80, Chestertown, MD 21620
    0.7 ACRES
    $55,000
    Map 36 Watertower Rd #80,
    Chestertown, MD 21620
    Doug Ashley Realtors, LLC
  • 8757 Orchard Dr, Chestertown, MD 21620
    1.89 ACRES
    $529,000
    2bd
    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
  • 24 & 25 Buck Neck Rd, Chestertown, MD 21620
    0.42 ACRES
    $8,000
    24 & 25 Buck Neck Rd,
    Chestertown, MD 21620
    Doug Ashley Realtors, LLC
  • Millbrook Dr, Chestertown, MD 21620
    1.08 ACRES
    $22,000
    Millbrook Dr,
    Chestertown, MD 21620
    Chesapeake Real Estate Associates, LLC
  • 209 Myers Rd, Chestertown, MD 21620
    1.23 ACRES
    $380,000
    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
    $25,000
    23690 L Rd,
    Chestertown, MD 21620
    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
  • 870 Washington Ave, Chestertown, MD 21620
    $285,000
    3bd
    1ba
    1,454 sqft
    870 Washington Ave,
    Chestertown, MD 21620
    Cross Street Realtors LLC
  • 106 Water 1/2 St N, Chestertown, MD 21620
    $695,000
    4bd
    4ba
    2,866 sqft
    106 Water 1/2 St N,
    Chestertown, MD 21620
    Cross Street Realtors 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 $353,842
MonthMedian home value
April 2023$334k
May 2023$336k
June 2023$340k
July 2023$342k
August 2023$344k
September 2023$345k
October 2023$346k
November 2023$348k
December 2023$349k
January 2024$350k
February 2024$351k
March 2024$354k
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 8 new listings and 63 homes for sale in Chestertown.
Home SizeHome Value*
2 bedrooms (9 homes)$273,793
3 bedrooms (17 homes)$328,896
4 bedrooms (5 homes)$453,307
*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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