USAMDChestertownChestertown Historic District105 High St
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105 High St, CHESTERTOWN, MD

House

For Sale

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

550

MLS® MDKE2005890

  • Key Facts
  • Description
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 3243 sqft
Garage Yes
Taxes $20,218
Days Active 28
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

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.
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

Similar Listings

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

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