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Glennmary is the work of master builder Dabney Cosby, Sr., who assisted with the original Jeffersonian buildings at the University of Virginia. Cosby is first recorded in an architectural capacity when he wrote Thomas Jefferson from Staunton offering his services as a bricklayer and brickmaker. Leaving Charlottesville, Cosby continued to design and build throughout southern Virginia. As noted in his account book, Glennmary was begun in 1837 for Archibald Glenn, son of a Halifax merchant.

Although a plantation dwelling, its three bay, side-hall-plan format is more commonly seen in urban housing. Typical of Cosby's works, Glennmary employs brickwork of the highest quality. By the time it was built, Cosby had veered from the purely Roman Classicism favored by Thomas Jefferson and was using Greek elements. Glennmary stood neglected for many years but was restored in the 1980's. A notable characteristic of the house is its large scale and exceptionally large windows.

The interior is noteworthy for its finely executed stair and woodwork. Dominating the hall is a single-run, open-well stair which ascends to the second floor. The stair features carved paneled spandrels, sawn-scroll brackets, rectangular balusters, and a finely turned newel post. The doorway in the hall and throughout the house have Greek revival mantels. The mantels were derived from Asher Benjamin's The Practical House Carpenter. Contemporary amenities have been discreetly incorporated providing modern upgrades while preserving the integrity of the house.
     

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