BEDS5
BATHS4 full 1 partial
SQUARE FEET3,243
MLS#MDKE2005890
STATUSACTIVE
PROPERTY TYPEResidential - Single Family
SUBDIVISIONCHESTERTOWN HISTORIC DISTRICT
SCHOOLKENT COUNTY PUBLIC SCHOOLS
Property Description
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.
Property Features
Property Type: Residential - Single Family
Basement: Yes
Basement: Improved, Interior Access
Cooling: Central A/C
Fireplaces: 2
Fuel Type: Electric, Propane - Leased
Garage: 1
Heating: Heat Pump(s)
Home Style: Victorian
Lot Size: 0.06 Acres
Stories: 4.0
Taxes: $20,218
Year Built: 1863
Feature Descriptions
Additional Structures: Above Grade, Below Grade
Exterior: Frame
Location: Downtown
Lot Dimensions: 0.06 Acre(S)
Municipality: Chestertown
Number of Rooms: 10
Parking Notes: 1 Total Parking Spaces
Rooms: Bedroom 2,Bedroom 3,Bedroom 1,Bathroom 1,Bathroom 2,Half Bath
Sewer: Public Sewer
Special View Info: Water, Scenic Vista, River
SQFT Above Finished: 3243
SQFT Total Finished: 3243
Structure Type: Detached
Total Garage/Parking Spaces: 1
Water: Public
Local Schools
School District: KENT COUNTY PUBLIC SCHOOLS
Listed By / Shown By
Listed By
Agency Name: Coldwell Banker Chesapeake Real Estate Company
Agency Phone: 4107780330
Shown By
Agent Name: The Ferguson Group
Agent Phone: (240) 731-8935
Agency Title: Berkshire Hathaway HomeServices Homesale Realty
First AmericanEstimate Your Payment
Estimated Payment
$ 5,197.63 per month $3,105.78 Principal & Interest $1,684.83 Property Tax $407.02 Homeowner's Insurance
105 High Street | MLS# MDKE2005890
This single family home located at 105 High Street, Chestertown, MD 21620 is currently listed for sale with an asking price of $1,395,500. This property was built in 1863 and has 5 bedrooms and 4 full and 1 partial baths with 3243 sq. ft. High Street is located in the CHESTERTOWN HISTORIC DISTRICT subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search CHESTERTOWN HISTORIC DISTRICT real estate on www.thefergusongroup.co today.