It is the grandest plantation house ever built in Marengo County and is one of the most significant remaining examples of Greek Revival architecture in Alabama.

Gaineswood was designed and built by General Nathan Bryan Whitfield, beginning in 1843 as a dog-trot cabin, an open-hall log dwelling.

By 1860, Whitfield owned as many as 7,200 acres and had 235 enslaved people working his land, which produced nearly 600 bales of cotton that year, though not all at Gaineswood.

When Gaines was serving as the U.S. Indian Agent, he is said to have met with the famous chief Pushmataha, of the Choctaw Nation, under an old post oak tree on what would become the Gaineswood estate.

The exterior features the use of eighteen fluted Doric columns and 14 plain square pillars to support the three porches, the main portico, and the porte-cochère.

Parterre gardens off of the main north portico and south porch are surrounded by low masonry and wood balustrades and feature period-appropriate plantings and marble statuary.

[5] The estate has three surviving outbuildings: a cook's house, a garden pavilion with eight fluted Corinthian columns, and a monumental gatehouse that date to the antebellum period.

The hallway features fluted Ionic columns in the main entrance hall with reception rooms to either side, one for each sex.

The mistress' bedroom features a large floor-to-ceiling semicircular bay with curved windows and is fronted by two fluted Corinthian columns.

About one mile (1.6 km) long, the canal was dug to a depth of more than 30 feet (9.1 m) deep through the underlying chalk in some areas; it quickly diverts the surface water into the river at Demopolis.

[1] Severe moisture damage to the ceiling and dome in the dining room was corrected under a Save America's Treasures grant.