$1,245,500 $6,686 est/mo Sourced by Back At You
105 High St,CHESTERTOWN, MD 21620
CHESTERTOWN, MD 21620
Description
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.
Details
| MLS # | MDKE2005890 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | Active-bright |
| Year | 1863 |
| Days On Site | 336 |
| Listing Provided By | Coldwell Banker Chesapeake Real Estate Company | Michael ONeill |
Features
| Bed(s) | 5 |
|---|---|
| Bath(s) | 5 Total |
| SQ Feet | 3,243 |
| Garage | 1 |
| Basement | Y |
| Story(s) | 4 |
| Zoning | R-3 |
| Acreage | 0.06 |
| Property View | Water, Scenic Vista, River |
Interior
| Rooms Total | 10 |
|---|---|
| Cooling | Central A/C |
| Heating Yes / No | Yes |
| Heating | Heat Pump(s) |
Exterior
| Construction Materials | Frame |
|---|---|
| Foundation Details | Permanent |
Parking
| Garage Yes / No | Yes |
|---|
Taxes
| Tax Annual Amount | 20218 |
|---|
Area Information
| State | MD |
|---|---|
| County | KENT MD |
| City | CHESTERTOWN |
| Zip Code | 21620 |
| Area | KENT MD |
| Community Name | CHESTERTOWN HISTORIC DISTRICT |
| School District | KENT COUNTY PUBLIC SCHOOLS |
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Learn More About This Property
| State | MD |
|---|---|
| County | KENT MD |
| City | CHESTERTOWN |
| Zip Code | 21620 |
| Area | KENT MD |
| Community Name | CHESTERTOWN HISTORIC DISTRICT |
| School District | KENT COUNTY PUBLIC SCHOOLS |
Listing Updated: October 4, 2026 at 12:41:13 AM PDT