MD
KENT
CHESTERTOWN
21620
105 HIGH STREET
105 HIGH STREET, CHESTERTOWN, MD 21620
Share Listing
Listing Type
Single Family
Listing Status
active
59
$1,395,500

Home Details for 105 HIGH STREET

Price
$1,395,500
Type
Residential
Bedrooms
5
Bathrooms
5.0
Square feet
3243
Year built
1863
Lot size acres
0.06
County
KENT
Garage
1
Basement
Interior Entry
Days on site
0
MLS Listing#
MDKE2005890
Property Description

This masterpiece is finally complete. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 and 2025 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Don't miss out on this perfect of historic charm with modern amenities walking distance to all Chestertown has to offer.

Property Features
  • Heating Information
    • Electric
    • Propane
    • Heat Pump
  • Cooling Information
    • Central Air
    • Electric
  • Parking
    • Garage
    • Detached
  • Waterfront and Water Access
    • River Front
  • Water Features
    • Public
  • Basement
    • Interior Entry
Listing Courtesy: Coldwell Banker Chesapeake Real Estate Company - 410-778-0330
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Last Updated: 2025-11-07 21:46:20
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205 E Ridgeville Blvd, Mt. Airy, MD 21771
Kelly Steichen
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