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105 High St, Chestertown, MD 21620

Chestertown
Local realty services provided by:CENTURY 21 Harris Hawkins & Co.
105 High St,Chestertown, MD 21620
$1,195,000
  • 5 Beds
  • 5 Baths
  • 3,243 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sun, Nov 01
    11:00 am - 01:00 pm
Listed by: michael oneill
Office: coldwell banker chesapeake real estate company
MLS#:MDKE2005890
Source:BRIGHTMLS

Price summary

  • Price:$1,195,000
  • Price per sq. ft.:$368.49

About this home

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Rebuilt after the fire of its day, the Tilley Residence has been brought back since 2022 by a top builder and his designer sister. A grand staircase, refinished by hand over many months, rises past glimpses of the water. The new custom kitchen is made for gathering. Upstairs, the primary suite has its own fireplace, and there are 4.5 brand-new baths. Below, a bright lower level holds a wine cellar. Everything unseen is new, too: HVAC, electrical, plumbing, roof and insulation. Outside, there’s a private fenced yard, a remodeled garage, and the historic Custom House next door. Shops, galleries, dining and the marina are all a short stroll away. There is no better chance to drop your keys and create your legacy in Chestertown's Historic District.

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Home facts

  • Year built:1863
  • Subdivision & Development:CHESTERTOWN HISTORIC DISTRICT
  • Listing ID #:MDKE2005890
  • Added:577 day(s) ago
  • Updated:October 26, 2026 at 02:01 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:$1,195,000
  • Price per sq. ft.:$368.49
  • Tax amount:$20,218 (2025)

Parking

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

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