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Victorian Homes for Sale in Kent County MD

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  • /48

    $1,295,500

    • 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 across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • /13

    $615,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 4,536 Sq Ft

    103 Maple Ave, Chestertown, MD 21620

    The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    103 Maple Ave, Chestertown, MD 21620
  • /39

    $515,000

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    101 S Mill St, Chestertown, MD 21620

    This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • /57

    $798,000

    $30K PRICE DROP
    • 3 Beds
    • 4.5 Baths
    • 3,047 Sq Ft

    407 High St, Chestertown, MD 21620

    Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    407 High St, Chestertown, MD 21620
  • /33

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    11901 Dairy St, Kennedyville, MD 21645

    Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    11901 Dairy St, Kennedyville, MD 21645
  • /33

    $379,900

    $40K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,927 Sq Ft

    104 Main St, Betterton, MD 21610

    Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Main St, Betterton, MD 21610
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