105 High St, Chestertown, MD 21620

Chestertown
Local realty services provided by:Better Homes and Gardens Real Estate Realty Connect
105 High St,Chestertown, MD 21620
$1,245,500
  • 5 Beds
  • 5 Baths
  • 3,243 sq. ft.
  • Single family
  • Active
Listed by: michael oneill
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2005890
Source:BRIGHTMLS

Price summary

  • Price:$1,245,500
  • Price per sq. ft.:$384.06

About this home

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.

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Home facts

  • Year built:1863
  • Listing ID #:MDKE2005890
  • Added:471 day(s) ago
  • Updated:July 13, 2026 at 02:11 PM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:5
  • Full bathrooms:4
  • Half bathrooms:1
  • Rooms Total:10
  • Bathrooms Description:Bathroom 1, Bathroom 2, Half Bath
  • Basement:Yes
  • Basement Description:Improved, Interior Access
  • Living area:3,243 sq. ft.

Heating and cooling

  • Cooling:Central A/C
  • Heating:Electric, Heat Pump(s), Propane - Leased

Structure and exterior

  • Year built:1863
  • Building area:3,243 sq. ft.
  • Lot area:0.06 Acres
  • Lot Features:Downtown
  • Architectural Style:Victorian
  • Construction Materials:Frame
  • Exterior Features:Patio(s), Porch(es)
  • Foundation Description:Permanent
  • Levels:4 Story

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$1,245,500
  • Price per sq. ft.:$384.06
  • Tax amount:$20,218 (2025)

Parking

  • Parking description:Detached Garage, Garage - Side Entry
  • Garage:Yes
  • Garage spaces:1

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