


522 High St, Chestertown, MD 21620
Listing Courtesy of Benson & Mangold, LLC



























Est.$2,532/moCustomize payment
$146/sqft
Price per square foot
Built in 1974
52 years old
3 parking spaces
Garage
Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first ...
Listing updated: May 27, 2026 at 6:56 AM
Listed by:
Robin Fithian 410-708-0279, Rock Hall Properties Real Estate
Source: Bright MLS · MLS #MDKE2005584
Est. monthly payment
Down payment
Based on 20% down ($77,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.
Rates provided by Mable Loans.
| Date | Event | Price |
|---|---|---|
| Apr 28, 2026 | Price increased | $385,000(+$60,000) |
| Aug 28, 2025 | Listed for sale | $325,000 |
23043 Bay Shore Spur, Chestertown, MD 21620
KENT COUNTY
High School
Similar homes sold within 0.5 miles in the last 90 days.

23055 Old Fairlee Rd
Chestertown, MD
$332K
Sold Apr 10, 2026 · Listed $330K

23110 Old Fairlee Rd
Chestertown, MD
$330K
Sold Apr 4, 2026 · Listed $340K
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.

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: 6/2/2026.