A Landmark Home in the Heart of Chestertown’s Historic District
Few homes capture the spirit of Chestertown quite like this. Built in 1863, the residence at 105 High Street stands as a rare opportunity to own a piece of Eastern Shore history — thoughtfully restored for modern living. This five-bedroom, four-and-a-half-bath Victorian combines 19th-century craftsmanship with 21st-century comfort. From the moment you step inside, you’re greeted by soaring ceilings, intricate millwork, and a grand three-story staircase that defines the home’s timeless character.
A Blend of History and Modern Comfort
Every detail tells a story. The chef’s kitchen has been fully updated with stainless appliances and elegant finishes, offering the perfect blend of heritage charm and functionality. Expansive living and dining spaces flow naturally for entertaining or quiet evenings at home, all surrounded by sun-filled windows overlooking Chestertown’s quaint streetscape. Upstairs, the primary suite offers a private retreat with updated luxury touches, while additional bedrooms provide space for family, guests, or even a home office with a view. With over 3,200 sq ft of interior space, plus a detached garage and off-street parking, this property delivers both beauty and practicality. The corner lot allows water views on two sides, bringing the Chesapeake light indoors throughout the day.
Location, Lifestyle, and Legacy
Situated just steps from the Chester River, the Chestertown Farmers Market, and beloved local shops, restaurants, and galleries, this home offers the perfect walkable lifestyle. Morning coffee on the porch, an evening at the Garfield Center for the Arts, or a riverside stroll at sunset — life here feels both peaceful and vibrant. As someone who lives and works on Maryland’s Eastern Shore, I can say with confidence: opportunities like this don’t come along often. 105 High Street is more than a property; it’s a living piece of Chestertown’s heritage — ready for its next chapter.
105 High Street, Chestertown, MD 21620. Offered Exclusively by Murphy O’Neill, Coldwell Banker Chesapeake
443-480-4275 | murphy@cbchesapeake.com
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