105 High St

Chestertown, MD 21620
  • $1,395,500

    Price
  • 5

    Bed
  • 4.5

    Bath
  • 3,243

    SqFt

Open House Times

  • Sat. Mar. 28 at 11:00am to 1:00pm

About the Listing CBCE2 - 3337613

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most 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 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.

Listing Highlights

Status Active
Days on Site 134
Property Type Residential
MLS ® MDKE2005890
Year Built 1863
Total Square Footage 3,243
Lot/Acreage 0.06

Interior Details

  • Bedrooms: 5
  • Bathrooms: 4 Full / 1 Half
  • Appliances:
  • Air Cond: Central A/C
  • Heating: Heat Pump(s)
  • Fireplaces: 2, 2 Fireplaces
  • Floor:
  • Above Ground Sq Ft: 3243
  • Below Ground Sq Ft: 0
  • Basement: Improved,Interior Access
  • Other:
  • Water: Public

Exterior Details

  • Lot Description: Not New Construction,Horse Property: No,In City Limits
  • Garage Capacity: 1 car
  • Parking Spaces: 1
  • Zoning: R-3
  • Roof:
  • Others:
  • Sewer: Public Sewer
  • Parking Features: Garage - Side Entry,Detached Garage,1+ Spaces

Financial Details

  • Tax Amount: $20,218
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: 2025

Payment Calculator

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Questions About..

105 High St Chestertown, MD 21620

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Originating MLS: BRIGHT_MAIN

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