About 105 High St
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.
Features of 105 High St
| MLS® # | MDKE2005890 |
|---|---|
| Price | $1,245,500 |
| Bedrooms | 5 |
| Bathrooms | 4.50 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 3,243 |
| Acres | 0.06 |
| Year Built | 1863 |
| Type | Residential |
| Sub-Type | Detached |
| Style | Victorian |
| Status | Active |
Community Information
| Address | 105 High St |
|---|---|
| Subdivision | CHESTERTOWN HISTORIC DISTRICT |
| City | CHESTERTOWN |
| County | KENT-MD |
| State | MD |
| Municipality | Chestertown |
| Zip Code | 21620 |
Amenities
| # of Garages | 1 |
|---|---|
| Garages | Garage - Side Entry |
| View | Water, Scenic Vista, River |
| Is Waterfront | No |
Interior
| Heating | Heat Pump(s) |
|---|---|
| Cooling | Central A/C |
| Has Basement | Yes |
| Basement | Improved, Interior Access |
| Fireplace | Yes |
| # of Fireplaces | 2 |
| Stories | 4 |
Exterior
| Exterior | Frame |
|---|---|
| Exterior Features | Porch(es),Patio(s) |
| Construction | Frame |
| Foundation | Permanent |
School Information
| District | KENT COUNTY PUBLIC SCHOOLS |
|---|
Additional Information
| Date Listed | November 7th, 2025 |
|---|---|
| Days on Market | 306 |
| Zoning | R-3 |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
| Listing Ownership | Fee Simple |
Listing Details
| Office | Coldwell Banker Chesapeake Real Estate Company |
|---|