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$1,395,500
118 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

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105 HIGH STREET105 HIGH STREET105 HIGH STREET105 HIGH STREET
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Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most 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 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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Listing Snapshot
Price 
$1,395,500
Days On Site 
118 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
yesterdayListing updated with changes from the MLS®
4 months 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
Bathroom 1 
Bathroom 2 
Bedroom 1 
Bedroom 2 
Bedroom 3 
Half Bath 
Level - Main
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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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Neighborhood & Commute
Source: Walkscore
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