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105 High St
For Sale $1,245,500 ($384.06 per Sq Ft)
$1,245,500 ($384.06 per Sq Ft)
- 5 Bedrooms
- 5 Bathrooms
- 3,243 Sq Ft
- 2,688 Sq Ft
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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Amenities
Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt
Upcoming Open House
Saturday July 11th, 2026
from 10:00 am - 12:00 pm
Property Details
| List Price | $1,245,500 |
| Property Type | Single Family Homes |
| Usable Sqft | 3,243 |
| Number of Stories | 0 stories |
| Parking Spots | 1 spots |
| Year Built | 1863 |
| Last Sold | Unknown |
| Sold Price | Unknown |
| APN # | 1504018273 |
| MLS # | MDKE2005890 |
| Property ID | 322337186 |
| Lot Sqft | 2,688 |
| Zoning | R-3 |
| Days on Market | 247 |
| Original List Price | Unknown |
| Date Updated | June 26, 2026 |
| Date Created | November 06, 2025 |
Listing Provided By
Michael ONeill an agent of . Lic #5010912
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Data last updated: July 11, 2026.
Robert Crawford
REAL ESTATE AGENT