


517 Round Top Road, Chestertown, MD 21620
Listing Courtesy of Keller Williams Flagship

Sold onMay 27, 2026· Listed at $299,000
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.
$212/sqft
Price per square foot
Built in 1975
51 years old
Located in the water-oriented community of Chester Harbor just outside of historic Chestertown, 154 Longfellow Drive offers the ideal blend of convenience and Eastern Shore living. This single-level home is situated on a cleared and fenced 0.34 acre-parcel and a voluntary HOA fee provides access to the community boat ramp and waterfront park. Less than a mile and a half from Route 213, enjoy efficient commuting and quick access to Chestertown, Church Hill, Centreville, Easton, and Kent Island. Inside the home, enjoy an updated full bath, a new HVAC system and well pump, a six year old septic ...
Listing updated: May 28, 2026 at 12:40 AM
Listed by:
Kaitlin Grace Stecklair 4107085414, Cross Street Realtors LLC
Source: Bright MLS · MLS #MDQA2016250
| Date | Event | Price |
|---|---|---|
| May 27, 2026 | Sold | $300,000 |
| Mar 13, 2026 | Listed for sale | $299,000 |
154 Longfellow Drive, Chestertown, MD 21620
Tell us what you're looking for and we'll send fresh matches near Chestertown the moment they list.
Find homes like thisFree, takes about a minute
Similar homes sold within 0.5 miles in the last 90 days.

114 Chester Vw
Chestertown, MD
$1.65M
Sold Jun 30, 2026 · Listed $1.65M
154 Longfellow Drive
Chestertown, MD
$300K
Sold May 27, 2026 · Listed $299K
513 Round Top Road
Chestertown, MD
$220K
Sold Apr 14, 2026 · Listed $225K
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.
Active listings within ~5 miles of this address.

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: 7/2/2026.