105 High St, Chestertown, MD 21620

Chestertown
Local realty services provided by:ERA Byrne Realty
105 High St,Chestertown, MD 21620
$1,395,500
Virtual Tour
  • 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:$1,395,500
  • Price per sq. ft.:$430.31

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.

Contact an agent

contact an agent

Yes, I would like more information. Please use and/or share my information with an ERA®  affiliated agent to contact me about my real estate needs. By clicking Send message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an ERA®  affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE® , CENTURY 21® , Coldwell Banker® , Corcoran® , Sotheby's International Realty® ). I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1863
  • Listing ID #:MDKE2005890
  • Added:367 day(s) ago
  • Updated:March 31, 2026 at 01:32 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:$1,395,500
  • Price per sq. ft.:$430.31
  • Tax amount:$20,218 (2025)

Parking

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

New listings near 105 High St