Save
Ask
Tour
Hide
$1,395,500
141 Days On Site
105 HIGH STREETCHESTERTOWN, MD21620
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: 443.632.3000
Is this the listing for you? We can help make it yours.
443.632.3000
Save
Ask
Tour
Hide
Mortgage Calculator
Monthly Payment (Est.)
$6,367Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.
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.
Save
Ask
Tour
Hide
Listing Snapshot
Price
$1,395,500
Days On Site
141 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
| 5 days ago | Listing updated with changes from the MLS® | |
| 5 months ago | Listing 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
Save
Ask
Tour
Hide
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
The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.
The real estate listing information is provided by Bright MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale or lease referenced on this web site comes from the Internet Data Exchange (IDX) program of the Bright MLS. This web site references real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. The accuracy of all information is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. Properties in listings may have been sold or may no longer be available. The data contained herein is copyrighted by Bright MLS and is protected by all applicable copyright laws. Any unauthorized collection or dissemination of this information is in violation of copyright laws and is strictly prohibited. Copyright © 2020 Bright MLS. All rights reserved.
Neighborhood & Commute
Source: Walkscore
Save
Ask
Tour
Hide