522 High Street

Chestertown MD 21620

1518 sq. ft.

3640 sq. ft.

Single-Family

Last sold for $290,000

Taylor Leaverton, last sold this property on 30 September 2026 after 122 days on market.

Overview

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

Features

2 bedrooms

3 bathrooms

1518 sq. ft. floor area

3640 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in Chestertown over the last 12 months, the estimated median property value of 522 High Street is $277.45k.

Median value

$277.45k

Estimated value range

$155k - $700k

Median days on market

Estimated value trend

-21%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Chestertown. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 522 High Street

2026

Sold

$290,000

30 Sep 2026 by Taylor Leaverton, of Benson & Mangold, LLC

Happy sellers in Chestertown

We have insufficient information to provide an overview of customer satisfaction for Chestertown. Viewing the agent profiles, reviews and sales for Chestertown can provide insights for this location.