Tom Boeshore
BEDS0
BATHS
SQUARE FEET3,243
MLS#MDKE2005890
STATUSACTIVE
PROPERTY TYPEResidential - Single Family
SUBDIVISIONCHESTERTOWN HISTORIC DISTRICT
SCHOOLKENT COUNTY PUBLIC SCHOOLS
Property Description
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.
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
Parking Notes: 1 Total Parking Spaces
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: Tom Boeshore
Agent Phone: Cell: (410) 739-4071
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
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
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 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.tomboeshorerealtor.com today.