6,886

Chestertown, MD Homes

Section Image
  • 108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    /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
    • 105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, Chestertown, MD 21620
      105 Sutton Way, 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

  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $449,999

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

    222 Mount Vernon Ave, Chestertown, MD 21620

    HIGHLY MOTIVATED SELLERS- DON'T MISS THIS OPPORTUNITY! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 141 Prospect St, Chestertown, MD 21620
    141 Prospect St, Chestertown, MD 21620
    141 Prospect St, 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
    • 112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, Chestertown, MD 21620
      112 Pine Tree Rd, 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

  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /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
  • 106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, 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
    • 118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, Chestertown, MD 21620
      118 Little Harbor Way Unit 102, 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

  • 105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    105 Pearl Creek Ln, Chestertown, MD 21620
    /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
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn 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
    • 331 Park Ln, Chestertown, MD 21620
      331 Park Ln, Chestertown, MD 21620
      331 Park 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

  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $539,999 Open Sat 10AM - 12PM

    • 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
  • 8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, 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
    • 228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, Chestertown, MD 21620
      228 Dutchess Rd, 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

  • 104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    /34

    $440,000

    • 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
  • 110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, 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
    • 102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, Chestertown, MD 21620
      102 Darden Rd, 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

  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /44

    $344,900

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft

    304 Hadaway Dr, Chestertown, MD 21620

    Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a

    Gregory Morris Cummings & Co. Realtors

    304 Hadaway Dr, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, 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
    • 310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      310 Longfellow Dr, Chestertown, MD 21620
      /27

      Est $342,811 Not Listed For Sale

      310 Longfellow Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 2002
      310 Longfellow Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $205/SF
      • 20 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    23069 Raleigh Rd, Chestertown, MD 21620
    /10

    $175,000 Pending

    • 2 Beds
    • 1,160 Sq Ft

    23069 Raleigh Rd, Chestertown, MD 21620

    Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Renters finally moved out and the house is being cleaned up. Roof was replaced in 2022.

    George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • 3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, 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
    • 414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      414 Pine Tree Rd, Chestertown, MD 21620
      /42

      Est $383,457 Not Listed For Sale

      414 Pine Tree Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,688 Sq Ft
      • Built 1968
      414 Pine Tree Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $207/SF
      • 47 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Kimberly Raeder Keller Williams Select Realtors of Annapolis

  • LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
    /3

    $9,500 Under Contract

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    Kent County Health Dept has no record of perc

    Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
  • 117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    117 Court St, 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
    • 122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      122 1st St, Chestertown, MD 21620
      /8

      Est $204,287 Not Listed For Sale

      122 1st St, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 720 Sq Ft
      • Built 1955
      122 1st St, Chestertown, MD 21620

      Last Sold Summary

      • 51% Above List Price
      • $188/SF
      • 5 Days On Market

      Last Sold Price $135,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • 0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    0 Johnsontown Rd, Chestertown, MD 21620
    /16

    $35,000 Under Contract

    • Land
    • 0.9 Acre
    • $38,889 per Acre

    0 Johnsontown Rd, Chestertown, MD 21620

    Vacant land along the Johnsontown Rd, Chestertown, MD and is conveniently located at the corner of Johnsontown Rd and Willow Oak Lane.

    David Amenyah Berkshire Hathaway HomeServices PenFed Realty

    0 Johnsontown Rd, Chestertown, MD 21620
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop 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
    • 204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      204 Princess Anne Dr, Chestertown, MD 21620
      /35

      Est $371,519 Not Listed For Sale

      204 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1984
      204 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $239/SF
      • 82 Days On Market

      Last Sold Price $359,000

      Last Listing Agent Jamil Wright EXP Realty, LLC

  • 2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    2 Scheeler Rd, Chestertown, MD 21620
    /7

    $250,000 Pending

    • Land
    • 0.93 Acre
    • $268,817 per Acre

    2 Scheeler Rd, Chestertown, MD 21620

    This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer

    William Norris Select Land & Homes, LLC

    2 Scheeler Rd, Chestertown, MD 21620
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, 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
    • 201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      /36

      Est $404,932 Not Listed For Sale

      201 Princess Anne Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft
      • Built 1998
      201 Princess Anne Dr, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $177/SF
      • 120 Days On Market

      Last Sold Price $370,247

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • 0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
    /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • 234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield 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
    • 124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      /18

      Est $308,436 Not Listed For Sale

      124 Wilton Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1976
      124 Wilton Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $275/SF
      • 9 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Jeff Guthrie Taylor Properties

  • 119 Darden Rd, Chestertown, MD 21620
    119 Darden Rd, Chestertown, MD 21620
    119 Darden Rd, Chestertown, MD 21620
    /19

    $275,000 Pending

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

    119 Darden Rd, Chestertown, MD 21620

    Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

    Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • 8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, 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
    • 317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      317 Union Church Rd, Chestertown, MD 21620
      /33

      Est $696,944 Not Listed For Sale

      317 Union Church Rd, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,512 Sq Ft
      • Built 2021
      317 Union Church Rd, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $273/SF
      • 0 Days On Market

      Last Sold Price $685,000

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /48

    $1,395,500 Open House 3/28

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    /2

    $11,000 Sold Feb 19, 2026

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    • Land
    • 2 Acres
    • $5,500 per Acre

    Last Sold Summary

    • 806 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

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