Link Copied
Listed price in listed location currency (USD).
$1,395,500

550

MLS® MDKE2005890

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 3243 sqft
Garage Yes
Taxes $20,218
Days Active 122
Lot Size 0.06 acres
Approx. Age 1863
Avg. Price Per Sqft $430
MLS® Number MDKE2005890

Property Address: 105 High St, CHESTERTOWN, MD, 21620-1515

Average square foot calculated using Size range provided by listing agent.

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.
MLS® NumberMDKE2005890
Laundry Level
Central VacNo
FireplaceNo
Acreage0.06
Exterior
GarageYes
Approx. Age1863
BasementImproved, Interior Access
DrivewayDetached Garage
Garage Spaces1
Heat
A/C
Heating Fuel

Extras

Rooms

Bathroom 4:Not available
Bedroom 4:Not available
Bathroom 3:Not available
Bedroom 1:Not available
Bedroom 5:Not available
Bathroom 1:Not available
Bedroom 3:Not available
Bathroom 2:Not available
Bedroom 2:Not available
Other:Not available

Price History

-End Date
Not Sold YetSold Price

For Sale

Nov 7, 2025List Date
$1,395,500List Price
  • Commute

Commute

Starting Address
Destination Address
105 High St, CHESTERTOWN, MD

Like what you see?

Complete the form and we'll be in touch. No login necessary.

Add a Comment
Loading...

Similar Listings

Comparable Properties