$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 4 months ago

Property Description

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.

Listing Status:
Active
Data Last Updated:
March 24, 2026 at 1:19AM
Listing Office:
Coldwell Banker Chesapeake Real Estate Company : 4107780330
Listing Agent:
Michael ONeill : 4434804275
MLS ID:
MDKE2005890
  • Rooms: Bedroom 2Bedroom 3Bedroom 1Bathroom 1Bathroom 2Half Bath
  • 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 $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

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

8276 BROAD NECK RD, Chestertown, MD 21620
Single-Family Home For Sale

$1,495,000

  • 4 bed |
  • 4 bath |
  • 3,383 sqft |
  • 19.81 acre lot
8276 BROAD NECK RD Chestertown, MD 21620

#MDKE2006216 - Coldwell Banker Chesapeake Real Estate Company