Change Real Estate Presents:

522 High Street
Chestertown MD 21620

For Sale: $450,000.00 Active

List Date: 2026-05-30

Chestertown
2 bedrooms
3 bathrooms
1,518 build ft2
3,640 land ft2

About This Property

✨ 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. 🏡✨

Listing Agent: Taylor Leaverton. Benson & Mangold, LLC 410-708-5775 taylorl@chesapeakebayproperties.com

Property Features

Location Information
County:
Subdivision: CHESTERTOWN HISTORIC DISTRICT
click to open map in a new window
Interior Features
Appliances:
Interior:
Laundry:
Furnished: None
Flooring: Wood
Water: Public
Cooling: None
Heating: Baseboard - Hot Water
Fireplaces: 1
Windows:
Utilities:
Sewer: Public Sewer
Exterior Features
Year Built: 1820
Subdivision Name: Chestertown Historic District
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Taylor Leaverton. Benson & Mangold, LLC 410-708-5775 taylorl@chesapeakebayproperties.com

Property Photos [Click to enlarge]

Bright © 2026 Bright, All Rights Reserved.

The data related to real estate for sale on this website comes in part from the INTERNET DATA EXCHANGE (IDX) program of the Bright MLS. Real estate listings held by brokerage firms other than this site owner are marked with the IDX logo.

IDX information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation or other purposes. All listing information is deemed reliable but not guaranteed.

This content was last refreshed on 2026-06-04 08:53 AM. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.

DMCA Notice