Eastern Shore of Maryland Real Estate Blog

The Tilley Residence: Historic Architecture Reimagined at 105 High Street

Some homes occupy an address. Others become part of a town’s identity. 105 High Street in Chestertown belongs firmly in the second category.

Known as the Tilley Residence, this five-bedroom home was rebuilt in 1863 and is an exceptional example of Second Empire architecture. Its prominent position near the foot of High Street places it across from the historic Custom House and only one block from the Chester River waterfront.

The residence underwent an extensive restoration completed in 2025. The work respects the home’s architectural character while introducing updated systems, refined finishes, and the comforts expected in a modern luxury property.

Inside, approximately 3,243 square feet of finished living space extends across three levels. Five bedrooms, four full bathrooms, a powder room, two fireplaces, and thoughtfully designed gathering spaces make the home equally suited to everyday living and entertaining.

The location is just as compelling as the architecture. From the front door, owners can walk to the waterfront promenade, restaurants, galleries, shops, Washington College, community events, and morning coffee at Evergrain.

What style of home is 105 High Street?

The Tilley Residence is a Second Empire home, an architectural style associated with mansard roofs, strong vertical proportions, decorative craftsmanship, and elegant nineteenth-century detailing.

Is 105 High Street close to the Chester River?

Yes. The home is approximately one block from Chestertown’s waterfront and enjoys views toward the river and surrounding historic streetscape.

Why is this a legacy property?

Historic significance, a prominent downtown location, an extensive restoration, and irreplaceable period architecture make 105 High Street more than a typical luxury home. It offers the opportunity to steward an important piece of Chestertown’s built history.

For buyers seeking a restored historic home on Maryland’s Eastern Shore, the Tilley Residence represents a rare combination of craftsmanship, location, and livability. Contact me to experience it privately.