7,032

Homes in ZIP Code 21620

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  • /40

    $600,000 Sold May 16, 2025

    108 N Queen St, Chestertown, MD 21620

    • 5 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • Built 1920

    Last Sold Summary

    • $237/SF

    Current Estimated Value $648,949

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
    • /33

      Est $705,114 Not Listed For Sale

      209 Landing Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft
      • Built 2009
      209 Landing Ln, Chestertown, MD 21620

      Last Sold Summary

      • 34% Above List Price
      • $219/SF
      • 209 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /67

    $498,500 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    *Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • /16

    $120,000 Sold Feb 27, 2026

    141 Prospect St, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 27% Below List Price
    • $104/SF
    • 33 Days On Market

    Current Estimated Value $165,814

    Last Listing Agent Jeff Guthrie Taylor Properties

    141 Prospect St, Chestertown, MD 21620
    • /18

      Est $1,389,591 Not Listed For Sale

      141 Round Top Creek Ln, Chestertown, MD 21620

      • Studio
      • Built 1900
      141 Round Top Creek Ln, Chestertown, MD 21620

      Last Sold Summary

      • 29% Below List Price
      • 194 Days On Market

      Last Sold Price $1,950,000

      Last Listing Agent Brian Gearhart Benson & Mangold, LLC

  • /24

    $799,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • /36

    $315,000 Sold Aug 29, 2025

    106 Wilton Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $298/SF
    • 18 Days On Market

    Current Estimated Value $318,287

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
    • /44

      Est $489,757 Not Listed For Sale

      204 N Mill St, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,890 Sq Ft
      • Built 1920
      204 N Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 32% Above List Price
      • $128/SF
      • 49 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /49

    $559,000 Under Contract

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

    216 Blakefield Dr, Chestertown, MD 21620

    The wait is over 216 Blakefield Drive is complete, ready for occupancy and you will not be disappointed. This is the last avaiable lot in this community so don't wait! Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
  • /27

    $280,000 Sold Jun 09, 2025

    100 Acorn Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft
    • Built 2004

    Last Sold Summary

    • $145/SF
    • 164 Days On Market

    Current Estimated Value $305,410

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
    • /7

      Not Listed For Sale

      128 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 5 Baths
      • 3,497 Sq Ft
      • Built 1900
      128 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • $152/SF
      • 6 Days On Market

      Last Sold Price $530,000

      Last Listing Agent Amanda Morgan Brenton Realty Group

  • /24

    $765,900 New Construction

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

    37 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 bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • /15

    $155,000 Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $166,934

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
    • /23

      Est $433,079 Not Listed For Sale

      101 S Kent St, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,356 Sq Ft
      • Built 1880
      101 S Kent St, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $276/SF
      • 58 Days On Market

      Last Sold Price $374,000

      Last Listing Agent Jennifer Gregorski Washington Fine Properties

  • /29

    $444,999

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    HIGHLY MOTIVATED SELLERS — bring us an offer! This historic 1916 home is comfortable, convenient, and move-in ready. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and walking distance from downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests.

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • /17

    $335,000 Sold Oct 03, 2025

    110 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 2023

    Last Sold Summary

    • $180/SF
    • 208 Days On Market

    Current Estimated Value $342,937

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
    • /54

      Est $658,839 Not Listed For Sale

      116 N Queen St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,110 Sq Ft
      • Built 1920
      116 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $289/SF
      • 1 Day On Market

      Last Sold Price $610,000

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • /70

    $649,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft

    11040 Kylie Ln, Chestertown, MD 21620

    Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, this beautifully situated property provides a secluded retreat where you can truly unwind and enjoy the outdoors. This spacious 4-bedroom, 3.5-bath home offers flexible living for families and guests alike. The layout includes the

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • /11

    $190,000 Sold Mar 04, 2026

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $18,905 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 20 Days On Market

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
    • /31

      Est $518,867 Not Listed For Sale

      107 Adela Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 3,406 Sq Ft
      • Built 2010
      107 Adela Way, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $129/SF
      • 35 Days On Market

      Last Sold Price $440,000

      Last Listing Agent Mike Herndon Engel & Völkers Annapolis

  • /50

    $445,000

    • 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
  • /19

    $270,000 Sold Mar 18, 2026

    119 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • Built 1997

    Last Sold Summary

    • 14% Below List Price
    • $190/SF
    • 14 Days On Market

    Current Estimated Value $317,087

    Last Listing Agent Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
    • /43

      Est $454,813 Not Listed For Sale

      105 Sutton Way, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2010
      105 Sutton Way, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $196/SF
      • 1 Day On Market

      Last Sold Price $405,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /65

    $499,000

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft

    206 Camelot Dr, Chestertown, MD 21620

    Enjoy three bedrooms on the main floor, including a spacious primary suite with its own private bath. The open-concept main living area seamlessly connects the kitchen, family room, and bright breakfast/sunroom — making everyday living and entertaining effortless. Hosting something more formal? A separate dining room is ready for the occasion. The second level features a generous living/rec room,

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
  • /18

    $636,383 Sold Apr 24, 2025

    3650 Gratitude Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,599 Sq Ft
    • Built 2025

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Last Listing Agent Tineshia Johnson NVR, INC.

    3650 Gratitude Way, Chestertown, MD 21620
    • /18

      Not Listed For Sale

      112 Pine Tree Rd, Chestertown, MD 21620

      • Built 1982
      112 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • $128/SF
      • 37 Days On Market

      Last Sold Price $200,000

      Last Listing Agent Tammy Rosendale Rosendale Realty

  • /74

    $449,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,961 Sq Ft

    105 Pearl Creek Ln, Chestertown, MD 21620

    Welcome to your private Eastern Shore retreat on 1.37 acres. Built in 2018, this beautiful custom one-level home is thoughtfully designed for relaxed, everyday living and effortless entertaining. Sun-filled and inviting, the open layout creates a warm, comfortable atmosphere—perfect for gathering with family and friends or enjoying quiet moments at home. The home features 3 bedrooms, 2.5 baths,

    Lona Todd Taylor Properties

    105 Pearl Creek Ln, Chestertown, MD 21620
  • /35

    $365,000 Sold Mar 28, 2025

    117 Court St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 744 Sq Ft
    • Built 1885

    Last Sold Summary

    • $491/SF
    • 23 Days On Market

    Current Estimated Value $389,617

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    117 Court St, Chestertown, MD 21620
    • /8

      Est $655,857 Not Listed For Sale

      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2009
      118 Little Harbor Way Unit 102, Chestertown, MD 21620

      Last Sold Summary

      • 23% Above List Price
      • $354/SF

      Last Sold Price $535,000

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  • /70

    $519,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • /18

    $205,000 Sold Jul 18, 2025

    310 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 2005

    Last Sold Summary

    • $169/SF
    • 24 Days On Market

    Current Estimated Value $220,493

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
    • /33

      Est $870,969 Not Listed For Sale

      331 Park Ln, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,184 Sq Ft
      • Built 1988
      331 Park Ln, Chestertown, MD 21620

      Last Sold Summary

      • 22% Below List Price
      • $513/SF
      • 11 Days On Market

      Last Sold Price $1,120,000

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

  • /36

    $495,000 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft

    515 N Kent St, Chestertown, MD 21620

    Nestled in the charming Byford Development, this beautifully renovated home exudes warmth and comfort, making it the perfect retreat. With a thoughtful renovation completed in 2020, this residence boasts a blend of traditional and farmhouse styles, featuring a stunning brick and vinyl exterior that invites you in. Step inside to discover a spacious 2,220 sq. ft. layout, where modern amenities

    Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • /34

    $237,000 Sold Jun 30, 2025

    898 Washington Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • Built 1967

    Last Sold Summary

    • $171/SF
    • 5 Days On Market

    Current Estimated Value $258,360

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
    • /23

      Est $330,061 Not Listed For Sale

      228 Dutchess Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,796 Sq Ft
      • Built 1978
      228 Dutchess Rd, Chestertown, MD 21620

      Last Sold Summary

      • 50% Above List Price
      • $122/SF
      • 105 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Stephanie Lehane RE/MAX

  • /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /3

    $553,500 Sold Apr 07, 2025

    234 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 2024

    Last Sold Summary

    • $231/SF
    • 0 Days On Market

    Current Estimated Value $574,123

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
    • /11

      Est $303,539 Not Listed For Sale

      102 Darden Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,144 Sq Ft
      • Built 1986
      102 Darden Rd, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $232/SF
      • 2 Days On Market

      Last Sold Price $265,000

      Last Listing Agent Jimmy White Long & Foster

  • /34

    $440,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft

    104 Garland Ave, Chestertown, MD 21620

    Welcome to 104 Garland Avenue — a Traditional styled home with Cape Cod inspired design, offering easy one-level living with 3 bedrooms and 2 full baths in desirable Queen Anne’s County. Set on a corner lot with mature landscaping and inviting curb appeal, this home blends comfort and opportunity. Inside, you’ll find a functional layout designed for everyday living, highlighted by a thoughtfully

    Casey Scattergood Cross Street Realtors LLC

    104 Garland Ave, Chestertown, MD 21620
  • /59

    $775,000 Sold Nov 08, 2025

    8293 Brices Mill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,836 Sq Ft
    • Built 1900

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Current Estimated Value $779,599

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 18

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