The Cullen Homestead Historic District is located in the center of the rural community known as Hopewell, a small crossroads village located northeast of Crisfield, Somerset County, Maryland. The village is oriented to several state and county roads. The original principal north-south road, Old State Road (MD 667), passes along the east side of the district, while Lawson Barnes Road borders the district on the north and south. Crisfield Road (MD 413) parallels the old right-of-way of the Eastern Shore Railroad, which passes due west of the district. The historic district consists of three principal structures. The original Cullen family house, known as the Cullen Homestead, is a two-story, four-part stepped profile frame dwelling built c. 1820, supported on a low brick foundation and sheathed with aluminum siding over the original weatherboards. The two-story one-room plan main block retains Federal modillion block cornices with decorative end boards, an interior end brick chimney with an exposed brick firewall, and much of its second quarter of the 19th-century interior woodwork. The adjacent 1 ½-story section is contemporaneous with a single-story hyphen originally serving as the dining room, and also retains period woodwork. The fourth section, a 1 ½-story kitchen southwest of the house, dates to the mid 19th century. The third principal structure in the district is a second Cullen family residence, the Jacob Hoke Cullen House, a large 2 ½-story asymmetrical H-shaped house that was erected in two distinct stages, beginning around 1880 with a T-shaped Victorian dwelling that was enlarged around 1910 by a reverse of the original T-shaped form resulting in the H-shaped plan. Other than an exterior layer of aluminum siding, the house survives largely intact with a mixture of Victorian and Colonial Revival stylistic exterior and interior finishes reflecting its two periods of construction. Standing behind the house is a single-story, single-bay frame garage dating from the early 20th century. Located between the two houses is the Cullen family cemetery, which contains a small collection of marble grave markers primarily dating to the 19th century.