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About This Home
This 5-bedroom, 5-bathroom single family at 105 HIGH Street in Chestertown, MD is listed for $1,295,500 ($399 per sqft). Built in 1863, the home offers 3,243 sqft of living space on a 0.06 acres lot.
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.
Key Features
- Built in 1863
- 0.06 acre lot
- 4 stories
- 1 parking spaces
- Fireplace
Property Details
Amenities
Monthly Cost Estimate
$6,929/mo
20% down · 6.5% · 30 years
Estimates only. Actual payments may vary.
Location
105 HIGH Street
Chestertown, MD 21620
CHESTERTOWN HISTORIC DISTRICT
Property Details
Construction
Parking
Heating
Cooling
Questions & Answers
This 5-bedroom, 5-bathroom single family at 105 HIGH Street is listed at $1,295,500 ($399/sqft). The estimated monthly payment is $5,614 based on 20% down at 6.5% interest.
Key features include: Built in 1863, 0.06 acre lot, 4 stories, 1 parking spaces, Fireplace.
This property is listed by Michael ONeill and can be reached at 4434804275 or murphy@cbchesapeake.com.
