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105 High Street photo 1
for sale
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$1,245,500

5beds
|
5baths
|
3,243sqft
|
1863built
105 High Street,Chestertown, MD 21620

Est.$8,190/moCustomize payment

What's special

$384/sqft

Price per square foot

Built in 1863

163 years old

1 parking spaces

Garage

Overview

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 po...

Listing updated: June 26, 2026 at 1:47 PM

Listed by:

Michael Oneill 4434804275, Coldwell Banker Chesapeake Real Estate Company

Source: Bright MLS · MLS #MDKE2005890Bright MLS

Property details

Cost estimate

Est. monthly payment

$8,629/mo
Principal & interest
$6,529
Property tax
$1,685
Home insurance (est.)
$415

Down payment

$249,10020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($249,100), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
Jun 26, 2026Price reduced$1,245,500(−$50,000)
May 1, 2026Price reduced$1,295,500(−$100,000)
Nov 7, 2025Listed for sale$1,395,500

Location

105 High Street, Chestertown, MD 21620

Recently sold nearby

Similar homes sold within 0.5 miles in the last 90 days.

206 S Water Street

Chestertown, MD

$545K

Sold Apr 30, 2026 · Listed $549K

4 bd3 ba2,008 sqft$273/sqft(-111%)

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Nearby homes

$1,245,500

5 beds · 5 baths · 3,243 sqft

Bright MLS

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated: 7/2/2026.