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$1,395,500
15 Days On Site

105 HIGH STREET
CHESTERTOWN, MD 21620

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,243
SqFt
$430
/SqFt
1863
Built
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
County:
KENT
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company
Call Now: 443-318-4514
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443-318-4514
105 HIGH STREET105 HIGH STREET105 HIGH STREET105 HIGH STREET
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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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Listing Snapshot
Price 
$1,395,500
Days On Site 
15 Days
Bedrooms 
5
Inside Area (SqFt) 
3,243 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.06 Acres
Year Built 
1863
MLS® Number 
MDKE2005890
Status 
Active
Property Tax 
$20,218
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Assessor
Friends & Family
Recent Activity
3 days agoListing updated with changes from the MLS®
2 weeks agoListing first seen on site
General Features
Acres 
0.06
Cross Street 
Water Street
Foundation 
Permanent
Garage 
Yes
Garage Spaces 
1
Levels 
Three Or More
Parking 
GarageDetached
Parking Spaces 
1
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
Special Circumstances 
Standard
SqFt Above 
3243
SqFt Total 
4235
Style 
Victorian
Water Source 
Public
Zoning 
R-3
Interior Features
Appliances 
Gas Water Heater
Basement 
Interior Entry
Cooling 
Central AirElectric
Fireplace 
Yes
Fireplaces 
2
Heating 
ElectricPropaneHeat Pump
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Exterior Features
Construction Details 
Frame
Patio And Porch 
PorchPatio
Pool Features 
None
View 
WaterRiverScenic
Waterfront Features 
River Front
Waterview 
WaterRiverScenic
Community Features
School District 
KENT COUNTY PUBLIC SCHOOLS
Schools
School District
KENT COUNTY PUBLIC SCHOOLS
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company



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