105 High St, Chestertown, MD 21620
- $1,245,500
- 5
- BD
- 5
- BA
- 3,243
- SqFt
- List Price
- $1,245,500
- Price Change
- ▼ $50,000 1782503244
- Days on Market
- 264
- Status
- ACTIVE
- MLS#
- MDKE2005890
- Bedrooms
- 5
- Bathrooms
- 5
- Full Baths
- 4
- Half Baths
- 1
- Living Area
- 3,243
- Lot Size (Acres)
- 0.06
- Style
- Victorian
- Year Built
- 1863
- County
- Kent
- School District
- Kent County Public Schools
Property 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.
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Additional Information
- Subdivision
- Chestertown Historic District
- Taxes
- $20218
- School District
- Kent County Public Schools
- Fireplaces
- 2
- Garage
- Yes
- Garage Spaces
- 1
- View
- Water, Scenic Vista, River
- Heating
- Heat Pump(s)
- Heating Fuel
- Electric, Propane - Leased
- Cooling
- Central A/C
- Water
- Public
- Sewer
- Public Sewer
- Room Level
- Half Bath: Main, Bathroom 1: Main, Bedroom 1: Upper 1, Bedroom 2: Upper 1, Bedroom 3: Upper 1, Bathroom 1: Upper 1, Bathroom 2: Upper 1, Bedroom 1: Upper 2, Bedroom 2: Upper 2, Bathroom 1: Upper 2
- Basement
- Yes
Mortgage Calculator
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: