105 High Street, Chestertown, MD 21620Asking Price of: $1,395,500

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View full listing details at http://www.homesale.com/lid=182740028

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.

Property Details

Address: 105 High Street, Chestertown, MD 21620
Bedrooms: 5
Bathrooms: 4 full1 partial
Size: 3,243 square feet
Type: Victorian
Subdivision: CHESTERTOWN HISTORIC DISTRICT
Area: Chestertown
School District: KENT COUNTY PUBLIC SCHOOLS
MLS ID: MDKE2005890
Status: ACTIVE

Property School Information

School District: KENT COUNTY PUBLIC SCHOOLS

Property Features

Garage: 1
Taxes: $20,218
Basement: Yes
Exterior: Frame
Parking Notes: 1 Total Parking Spaces
Special View Info: Water,Scenic Vista,River
Lot Size: 0.06 Acres
Lot Dimensions: 0.06 Acre(S)
Heating: Heat Pump(s)
Fuel Type: Electric,Propane - Leased
Cooling: Central A/C
Year Built: 1863
Fireplaces: 2
Water: Public
Sewer: Public Sewer
Stories: 4.0
Number of Rooms: 10
Municipality: Chestertown
Additional Structures: Above Grade,Below Grade
Location Description: Downtown
Structure Type: Detached
Total Garage/Parking Spaces: 1
Rooms: Bedroom 2,Bedroom 3,Bedroom 1,Bathroom 1,Bathroom 2,Half Bath
Basement: Improved,Interior Access
SQFT Total Finished: 3243
SQFT Above Finished: 3243

Property information as of Friday, April 17, 2026 at 10:51 PM America/New_York

Listed By

Agency Name: Coldwell Banker Chesapeake Real Estate Company
Agency Phone: 4107780330

Shown By

Agency Title: Berkshire Hathaway HomeServices Homesale Realty
Agency Phone: +18003833535

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