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$798,000

3beds
|
5baths
|
3,047sqft
|
1780built
407 High St,Chestertown, MD 21620

Est.$5,247/moCustomize payment

What's special

$262/sqft

Price per square foot

Built in 1780

246 years old

2 parking spaces

Garage

Overview

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

Listing updated: June 14, 2026 at 10:00 AM

Listed by:

Lisa P Raffetto 410-708-0174, Coldwell Banker Chesapeake Real Estate Company

Source: Bright MLS · MLS #MDKE2006496Bright MLS

Property details

Cost estimate

Est. monthly payment

$5,348/mo
Principal & interest
$4,183
Property tax
$898
Home insurance (est.)
$266

Down payment

$159,60020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($159,600), 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 3, 2026Price reduced$798,000($30,000)
May 7, 2026Listed for sale$828,000

Location

407 High St, Chestertown, MD 21620

Nearby schools

KENT COUNTY

High School

Recently sold nearby

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

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

$798,000

3 beds · 5 baths · 3,047 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: 6/24/2026.