


121 Metcalf Road, Chestertown, MD 21620
Listing Courtesy of Real Broker, LLC - Chester


























Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA—blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private ...
Listing updated: July 14, 2026 at 3:00 PM
Listed by:
Sarah E. King (410) 708-2528, Cross Street Realtors LLC
Source: Bright MLS · MLS #MDKE2006668
Est. monthly payment
Down payment
Based on 20% down ($55,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.
Rates provided by Mable Loans.
| Date | Event | Price |
|---|---|---|
| Jul 14, 2026 | Price reduced | $275,000(−$9,900) |
| Jun 12, 2026 | Listed for sale | $284,900 |
104 Acorn Drive, Chestertown, MD 21620
Est. monthly payment
at 20% down · $275,000 list
Tour for free, no strings attached
Mable Loans · Equal Housing Lender
NMLS #1949497
Similar homes sold within 0.5 miles in the last 90 days.

108 Pine Street
Chestertown, MD
$85K
Sold Jun 30, 2026 · Listed $115K
112 Elm Street
Chestertown, MD
$249K
Sold Jun 12, 2026 · Listed $270K
115 Acorn Drive
Chestertown, MD
$290K
Sold Jun 4, 2026 · Listed $296K
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.
$1,853/mo
Est. · $275,000 list

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: 7/16/2026.