The incorporated town of Brookeville, Maryland, is situated on a plateau overlooking Reddy Branch in an arc to the north. Brookeville is a crossroads village, with almost all of the houses found along the two main streets, Market and High. The majority of the structures were built before 1900, and range in style from the Federal-style Jordan House to the simple, vernacular cabin known as the Blue House. The houses are built of stone, brick, and frame, and cover a period from 1779 to the 1950s. Most of the new buildings are located on the southern approach to the town, and are built in a modern colonial form not incompatible with the rest of the town. The 45 buildings in Brookeville, 35 of which are more than 50 years old, include four brick and three stone structures; the rest are of frame. Most of them are situated on quarter-acre lots. With the exception of the Post Office and plumbing shop, the town is a residential one. Of particular interest are the many outbuildings and the brick sidewalks.
The town of Brookeville was established in 1794 by Richard Thomas on land inherited by his wife, Debra, from her grandfather, James Brooke the elder, a Quaker. At that time there were three houses in the community: the Madison House, the Blue House, and the Valley House. Fifty-six lots were laid out by Richard Thomas, 20 of which were sold by 1806. Brookeville grew and thrived as it met the demands of the many prosperous farms which surrounded it. By 1813 the thriving rural community had 14 houses, two mills, a tanning yard, two stores, a blacksmith's shop, a post office, a boys school, and a constable. The town continued to flourish in the 19th century as additional shops and services, including a girls' school, two churches, and a cemetery were added. Brookeville was important locally as the center of commerce and education. It also has national significance as the home of the Bentley and Moore families, both of which were nationally prominent and were instrumental in founding the U.S. Department of Agriculture. Attesting to this is the fact that President Madison sought shelter for the night at the home of Caleb Bentley on August 26, 1814, when the British occupied Washington during the War of 1812. Brookeville is a unique town in Montgomery County because of its collection of unaltered early- and mid-19th century architecture and its pristine setting. Although several nearby towns have suffered from encroachment by residential development, Brookeville remains relatively untouched, with its narrow, curving streets and great trees. The houses represent most periods of architecture from the late 18th century to the 20th, but predominantly the Federal and mid 19th century, with Victorian touches. These are typical examples of these styles, in largely unaltered condition.