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105 High St
For Sale $1,395,500 ($430.31 per Sq Ft)
$1,395,500 ($430.31 per Sq Ft)
- 5 Bedrooms
- 5 Bathrooms
- 3,243 Sq Ft
- 2,688 Sq Ft
Description
This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House.
Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.
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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 December 6th, 2025
from 12:00 pm - 2:00 pm
Property Details
| List Price | $1,395,500 |
| 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 | 30 |
| Original List Price | Unknown |
| Date Updated | November 24, 2025 |
| Date Created | November 06, 2025 |
Listing Provided By
Michael ONeill an agent of . Lic #5010912
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Data last updated: December 06, 2025.
Robert Crawford
REAL ESTATE AGENT