105 HIGH ST,CHESTERTOWN,MD,21620,KENT

Chestertown, MD 21620

$1,245,500

active
5
Beds
5
Baths
3,243
Sq Ft
1863
Built

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105 HIGH ST,CHESTERTOWN,MD,21620,KENT - Photo 1

Listing details

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 systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

Location

Listed by Michael ONeill, Coldwell Banker Chesapeake Real Estate CompanyMLS# 804298812462Listing via Bright MLS IDXUpdated Jun 26, 2026

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Listing information is provided through IDX courtesy Keller Williams Capital Properties.

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