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5 Beds
5 Baths
3,243SqFt
Active
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.
Property Details | ||
|---|---|---|
| Price | $1,245,500 | |
| Bedrooms | 5 | |
| Full Baths | 4 | |
| Half Baths | 1 | |
| Total Baths | 5 | |
| Property Style | Victorian | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.06 | |
| Property Type | Residential | |
| Sub type | SingleFamilyResidence | |
| MLS Sub type | Detached | |
| Stories | 4 | |
| Year Built | 1863 | |
| Fireplaces | 2 | |
| Subdivision | CHESTERTOWN HISTORIC DISTRICT | |
| View | Water,Scenic Vista,River | |
| Heating | Heat Pump(s) | |
| Foundation | Permanent | |
| Accessibility | None | |
| Garage spaces | 1 | |
Geographic Data | ||
| Directions | From Chestertown's waterfront at the end of High Street, walk past the Customs House (one of the original British Ports of Entry) then it will be the next house on your left. | |
| County | KENT | |
| Latitude | 39.20731 | |
| Longitude | -76.06417 | |
Address Information | ||
| Address | 105 HIGH ST, CHESTERTOWN, MD 21620 | |
| Postal Code | 21620 | |
| City | CHESTERTOWN | |
| Cross Street | Water Street | |
| State | MD | |
| Country | United States | |
Listing Information | ||
| Listing Office | Coldwell Banker Chesapeake Real Estate Company | |
| Listing Agent | Michael ONeill | |
| Special listing conditions | Standard | |
| Ownership | Fee Simple | |
| Virtual Tour URL | https://www.youtube.com/watch?v=bOoR9Fi5cM8&t=1s | |
School Information | ||
| District | KENT COUNTY PUBLIC SCHOOLS | |
MLS Information | ||
| Days on market | 320 | |
| MLS Status | Active | |
| Listing Date | Nov 7, 2025 | |
| Listing Last Modified | Sep 22, 2026 | |
| Tax ID | 1504018273 | |
| Tax Year | 2025 | |
| Tax Annual Amount | 20218 | |
| MLS # | MDKE2005890 | |
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Last updated: 2026-09-23T01:00:25.249608Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.