105 High Street
Chestertown, MD, United States
$1,245,500
Active

105 High Street Chestertown, MD 21620

Property Features

  • 5 Beds
  • 4 Full Baths
  • 1 Half Baths
  • 3,243 sqft
  • MLS # MDKE2005890
  • Lot Size: 0.06 acres
  • Year Built: 1863

Attachments

Property Description

From Chestertown's waterfront at the end of High Street, walk past the Customs House (one of the original British Ports of Entry) then it will be the next house on your left.

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 Highlights

  • Tax Roll Number: 1504018273
  • Annual Tax: $ 20218.0

Location

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The listing broker’s offer of compensation is made only to participants of the multiple listing service where the listing is filed.

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