The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant - William Smith - living in an important hub for grain and tobacco. This Town and the area was the hub for grain to be used locally and sent abroad.

The history of Hillsboro spans from the late Colonial and Federal periods through the Victorian age and into our modern time. Historical records show that the first Episcopal Church was founded around 1768 and a small bridge was constructed over the Tuckahoe River around the same time.

The original land grant was given to Thomas Hardcastle, a famous personage in Caroline County's Colonial history.

This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The property is comprised of .66 acres of gardens and mature trees in the heart of Hillsboro.

The house has been altered slightly through the many decades, but the character of the original building dominates the architecture and "feel" of its 1794 era. Its charm and elegance remain. The rooms are commodious and inviting. The grand center ENTRANCE HALL is punctuated by the graceful stair, fine woodwork and doors. The LIVING ROOM, as expected, is spacious and comfortable with fireplace (now gas fired), original floors, and bookshelves. The DINING ROOM, of a grand size, features a fireplace (now gas), cabinetry and glass front cupboards. Two steps down from the dining Room the fully equipped KITCHEN is found with wood floor, exposed rafters and back stairway. Open from the kitchen is the GATHERING ROOM with wood floor and wide views of the grounds and gardens. A paver path from this room leads to the driveway and parking. An open DECK offers a secluded retreat off the kitchen wing

BEDROOMS and BATHS are found on second floor. Two of which have fireplaces although decorative at this time. Access to the bedroom level is either from the main grand stairway or via the back stairs. Adding to the charm is the back stair hall in the primary bedroom wing located over the kitchen and "gathering" room. The baths are delightful.

A surprise outbuilding is to the rear of the grounds. A perfect spot for an office, studio or storage. Another smaller outbuilding offers more storage. The grounds feature tall mature trees and fencing. The William Smith House is all one would expect built in a gracious era with a colorful history.
WHERE IS HILLSBORO?? Hillsboro lies a short distance from both Denton, Caroline County and Easton in Talbot County. Chestertown, in Kent County, is just 40 minutes. Annapolis, the Capitol of Maryland, is less than an hour. Unique shops, sailing facilities, live theater and restaurants abound. Hillsboro is from 1- 2 hours from the "rest of the world" for BWI, National and Philadelphia airports are a swift drive away. Dulles a bit further. A private airport is found in Easton. - 15 minutes. Atlantic Ocean resorts are about an hour. Adkins Arboretum is 1.5 miles. Adkins is a 400-acre native garden and preserve, provides exceptional experiences in nature to promote environmental stewardship. The Hillsboro Public Landing on the Tuckahoe is just a block from property. This property and lifestyle is an enriching experience” It awaits its next steward(s).

Hillsboro - In the years preceding the Revolutionary War, Hillsboro was renamed in honor of Lord Hillsboro of the Calvert Family, the original founders of Maryland. Early Hillsboro was a very affluent town. In 1797, the Hillsboro Academy was constructed on land donated by John Hardcastle, a descendant of Thomas Hardcastle, an early colonial founder in Caroline County. It was a small brick schoolhouse that served as an academy for local citizens of prominence from Caroline, Queen Anne's, and Talbot Counties. The school was funded by private donations and flourished until the Denton Academy was established in 1827. The highlights of Hillsboro's history were during the Colonial and Federal periods but many wonderful homes were constructed within the Town in later decades and represent a mix of traditional Victorian, Gothic, and Greek-Revival. The great American portrait painter Charles Wilson Peale lived for a short time in the Town.