105 High St, Chestertown, MD 21620

Local realty services provided by:Better Homes and Gardens Real Estate GSA Realty
105 High St,Chestertown, MD 21620
$1,395,500
  • 5 Beds
  • 5 Baths
  • 3,243 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sat, Nov 22
    11:00 am - 01:00 pm
Listed by: michael oneill
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2005890
Source:BRIGHTMLS

Price summary

  • Price:$1,395,500
  • Price per sq. ft.:$430.31

About this home

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.

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Home facts

  • Year built:1863
  • Listing ID #:MDKE2005890
  • Added:236 day(s) ago
  • Updated:November 20, 2025 at 02:49 PM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:5
  • Full bathrooms:4
  • Half bathrooms:1
  • 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

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$1,395,500
  • Price per sq. ft.:$430.31
  • Tax amount:$20,218 (2025)

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