$1,395,500

105 HIGH ST, Chestertown, MD 21620

  • 5 beds |
  • 5 baths |
  • 3,243 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1863
  • Property Lot Size Icon2,614sqft lot
  • Property Parking Icon 1 car garage
  • Property Price Per Square Feet Icon $430/sqft
  • Property List Date Icon Listed 1 month ago

Property Description

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.

Listing Status:
Active
Listing Office:
Coldwell Banker Chesapeake Real Estate Company : 4107780330
Listing Agent:
Michael ONeill : 4434804275
MLS ID:
MDKE2005890
  • Basement: ImprovedInterior access
  • A/C: Central A/C
  • Heating: Heat Pump(s)ElectricPropane - Leased
  • Fireplace: FireplaceFireplaces: 2
  • Disability Feature: None
  • General: Above GradeBelow Grade
  • Style: Victorian
  • Other Structures: PorchPatio
  • General: Frame4Permanent
  • Originating MLS: BRIGHT_MAIN
  • School District: KENT COUNTY PUBLIC SCHOOLS
  • County: KENT-MD
  • Zoning: R-31504018273
  • View: WaterScenic VistaRiver
  • Water: Public
  • Sewer: Public Sewer
  • Source: BRIGHT_MAIN

This listing courtesy of Michael ONeill, Coldwell Banker Chesapeake Real Estate Company

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

H

Henry Highland Garnet Elementary School

320 Calvert St, Chestertown, MD, 21620

Grades PK-5

0.52 miles away

K

Kent County Middle School

402 E Campus Ave, Chestertown, MD, 21620

Grades 6-8

0.74 miles away

K

Kent County High School

25301 Lambs Meadow Rd, Worton, MD, 21678

Grades 9-12

5.59 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.

Similar Listing

105 HIGH ST, Chestertown, MD 21620
Single-Family Home For Sale

$1,395,500

  • 5 bed |
  • 5 bath |
  • 3,243 sqft |
105 HIGH ST Chestertown, MD 21620

#MDKE2005002 - Coldwell Banker Chesapeake Real Estate Company