A prominent building on a principal approach into town, Glenanna and its several outbuildings were constructed for Dr. Tazewell Headen. One of a number of surviving nineteenth-century buildings erected by Dillon, the two-story house of brick laid in Flemish bond has a modified double-pile center-passage plan. It has numerous Greek Revival features typically found in larger post-Civil War dwellings, including a deck-on-hip roof. Perhaps the most distinctive feature of the facade is the monumental pedimented portico, an early-twentieth-century replacement of the original. Outbuildings that include a kitchen/servant's house, a springhouse, a smokehouse, and two log stables stand within a landscaped yard, fronted by a handsome iron fence. Physician Thomas H. Howard purchased the house in 1870.