Holly Oak (listed April 2017) is a Georgian-style, three-bay, two-and-a-half-story, stone and frame dwelling, located three miles south of the Pennsylvania and Delaware border, in the vicinity of Claymont, Brandywine Hundred, Delaware. Constructed by Caleb Perkins in 1774, the dwelling originally consisted of an early log portion and the current stone main core. The Perkins family owed the dwelling until 1854, but had sold off pieces the original 154 acre parcel of land and tenant farmers inhabited the house. Charles P. Mahoney, an iron merchant, purchased the property in 1854, but allowed the tenant Xavier Lapier (French immigrant and flag maker by trade) to remain in the dwelling. John H. Longstreet, president of the Philadelphia Real Estate Investment Company and the president and treasurer of the Lawndale Land Company, bought the property in 1889. Longstreet reassembled the original 154-acre tract of land that once belonged to the Perkins family, along with additional acreage, and plotted the “Holly Oak” subdivision in 1901. However, this subdivision never came to fruition. The rear service ell was added between 1900 and 1920, and by 1940 the stone sun room to the southeast was constructed.
Holly Oak was nominated under criterion "A" and "C." The dwelling is significant under Criterion A, for its association with the historic theme of stone construction in Brandywine Hundred, Delaware, which occurred from 1770 to 1960. Additionally, the house was nominated under Criterion "C" as being an example of Federal Style architecture in rural Delaware.