The Greensburg Academy is located at the corner of West Second and West Court Streets in Greensburg, county seat of Green County, Kentucky. The Academy faces east from Buckner's Hill across a shallow valley towards the town square. Buckner's Hill, the western-most of three gentle hills over which the town is spread, is now an uncrowded residential district. The town square is situated on the middle of the three hills, and the eastern-most hill constitutes what is now called the New Addition; a residential district that is new by name only, since its three earliest homes date to the early nineteenth century The Academy has a dramatic view of both the town and the New Addition, and although it is now in a residential setting, the one and one-half acre plot on which it is located preserves its natural setting. The hillside is terraced with several hundred feet of limestone walls, which are fairly well preserved. Of the outbuildings that once stood, only the springhouse built into the hillside still stands, although the remains of the slave quarters are still visible.

The present building consists of two parts, though remains of a third section are visible to the right of it. The earlier section of the building, built c. 1794-1818, is built into the hillside, so that its two and one-half stories are fully exposed on the facade, while only the top floor and one-half are revealed on the rear. The brick walls are approximately two feet thick and are laid in common bond, except for the facade, which is laid in Flemish bond with queen closures at the north end. - NRHP, June 1976