example of a best old house in the neighborhood of maryland
Photo: Courtesy of Maryland Heritage Properties
« »

Chestertown, Maryland

Once a bustling 18th-century seaport on Maryland's Eastern Shore, Chestertown is gaining favor among retirees who like living in a landmarked historic district that feels about the same as it did a hundred years ago. Here older folks comingle with students from Washington College in the town's coffee shops and pubs. And most residents take advantage of the Chester River, whether it's for kayaking, canoeing or fishing.

The Houses
The town is known chiefly for its stately 18th- and 19th-century brick mansions, though there are many later, Victorian-era houses here, too. Like Charleston, South Carolina, Chestertown has long been known for its passion for restoring and maintaining its older homes, so there are few fixer-uppers left. Occasionally a dilapidated Stick-style house might go on the market for $200,000, but most homes are restored and sell in the $500,000 to $800,000 range. A waterfront Colonial Revival here can go for several million.

Why Buy Now?
If you're looking for a great place to retire, buy in Chestertown now, since prices are as low as they're likely to get anytime soon (thanks, recession!). Though it's isolated in a rural region, Chestertown just over an hour from Washington, D.C., and Baltimore.

Among the best for: College Towns, Northeast, Outdoor Activities, Retirees, Waterfront
Ask TOH users about Home & Real Estate

Contribute to This Story Below