6,890

Chestertown, MD Homes

Section Image
  • 0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    0 Lenapah Rd, Chestertown, MD 21620
    /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 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:55 PM. 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 major

    Adam Shpritz Ashland Auction Group LLC

    0 Lenapah 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
    • 36,154 Sq Ft
    • $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
    • 103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      /42

      Est $319,311

      Not Listed For Sale

      103 Creston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 1973
      103 Creston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

  • 517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    517 Round Top Rd, Chestertown, MD 21620
    /28

    $299,900

    $50K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft

    517 Round Top Rd, Chestertown, MD 21620

    An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been

    Barry Hess Keller Williams Flagship

    517 Round Top 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 $388,656

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
    • 116 Fairview Dr, Chestertown, MD 21620
      116 Fairview Dr, Chestertown, MD 21620
      116 Fairview Dr, Chestertown, MD 21620
      /21

      Est $299,690

      Not Listed For Sale

      116 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,028 Sq Ft
      • Built 1976
      116 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

  • 0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    0 East St, Chestertown, MD 21620
    /8

    $88,900

    Pending
    • Land
    • 20,908 Sq Ft
    • $185,208 per Acre

    0 East St, Chestertown, MD 21620

    This corner lot offers a rare opportunity to build just minutes from Downtown Chestertown. Located on a quiet street and close to the Chester River, this property combines a peaceful setting with everyday convenience.The lot is perc approved and has site plans—see documents for details. With close proximity to Chestertown’s shops, galleries, and restaurants, it’s the perfect setting for those

    William Norris Select Land & Homes, LLC

    0 East St, 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
    • 218 Concord Rd, Chestertown, MD 21620
      218 Concord Rd, Chestertown, MD 21620
      218 Concord Rd, Chestertown, MD 21620
      /22

      Est $345,404

      Not Listed For Sale

      218 Concord Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 1997
      218 Concord Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    7828 Country Club Ln, Chestertown, MD 21620
    /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
  • 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 $374,615

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    104 Iris Rd, Chestertown, MD 21620
    • 411 Fairview Dr, Chestertown, MD 21620
      411 Fairview Dr, Chestertown, MD 21620
      411 Fairview Dr, Chestertown, MD 21620
      /30

      Est $585,466

      Not Listed For Sale

      411 Fairview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1977
      411 Fairview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 27 Days On Market

  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /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
  • 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 $290,264

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
    • 6744 Church Hill Rd, Chestertown, MD 21620
      6744 Church Hill Rd, Chestertown, MD 21620
      6744 Church Hill Rd, Chestertown, MD 21620
      /41

      Est $325,031

      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

  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $384,000

    $61K PRICE DROP Under Contract
    • 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
  • 24339 Chestertown Rd, Chestertown, MD 21620
    24339 Chestertown Rd, Chestertown, MD 21620
    24339 Chestertown Rd, 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 $265,283

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    24339 Chestertown Rd, Chestertown, MD 21620
    • 240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      /34

      Est $463,518

      Not Listed For Sale

      240 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,067 Sq Ft
      • Built 2003
      240 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 23 Days On Market

  • 0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    0 Montgomery Unit MDKE2003418, Chestertown, MD 21620
    /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
  • 23055 Old Fairlee Rd, Chestertown, MD 21620
    23055 Old Fairlee Rd, 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 $328,285

    Last Listing Agent Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
    • 209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      /26

      Est $422,506

      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

  • 0 Sheldrake Dr, Chestertown, MD 21620
    0 Sheldrake Dr, Chestertown, MD 21620
    /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
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee 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 $324,595

    Last Listing Agent Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
    • 112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      /21

      Est $358,661

      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

  • 201 River Rd, Chestertown, MD 21620
    201 River Rd, Chestertown, MD 21620
    201 River Rd, Chestertown, MD 21620
    /46

    $629,900

    Under Contract
    • 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
  • 0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, 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
    • 1316 Ewingtown Rd, Chestertown, MD 21620
      1316 Ewingtown Rd, Chestertown, MD 21620
      1316 Ewingtown Rd, Chestertown, MD 21620
      /60

      Est $641,708

      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

  • 109 Cedar St, Chestertown, MD 21620
    109 Cedar St, Chestertown, MD 21620
    109 Cedar St, Chestertown, MD 21620
    /22

    $325,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 1,397 Sq Ft

    109 Cedar St, Chestertown, MD 21620

    Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind

    Liddy Campbell TTR Sotheby's International Realty

    109 Cedar St, Chestertown, MD 21620
  • 349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, Chestertown, MD 21620
    349 & 351 High St, 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
    • 2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      2607 Mcginnes Rd, Chestertown, MD 21620
      /24

      Est $307,880

      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

  • 23710 L Rd, Chestertown, MD 21620
    23710 L Rd, Chestertown, MD 21620
    /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
  • 8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, Chestertown, MD 21620
    8750 Georgetown Rd, 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 $346,651

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
    • 208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      208 Central Dr, Chestertown, MD 21620
      /23

      Est $298,424

      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

  • 210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    210 N Queen St, Chestertown, MD 21620
    /36

    $735,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    210 N Queen St, Chestertown, MD 21620

    Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    210 N Queen St, Chestertown, MD 21620
  • 216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, Chestertown, MD 21620
    216 Blakefield Dr, 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 $554,289

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
    • 112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      112 Sheaffer Rd, Chestertown, MD 21620
      /48

      Est $539,832

      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

  • 214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    214 Silver Heel Rd, Chestertown, MD 21620
    /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
  • 26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, Chestertown, MD 21620
    26933 Mallard Rd, 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 $573,825

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, 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 $215,698

      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

  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /25

    $375,000

    • 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

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