Using lumber pre-measured and cut at Syracuse, New York and shipped to Florida, businessman Thomas Orman built this house overlooking Scipio Creek and the Apalachicola River in 1838. House features incorporate details of both Federal and Greek Revival styles. Having arrived from a plantation north of Marianna, Orman quickly gained prominence in Apalachicola as a highly successful mercantile store proprietor, shipping owner, and cotton merchant. As a Confederate sympathizer, Orman was arrested and detained for a short time by Union authorities during the Civil War. His 26 slaves were freed by Union troops and transported to Union-held Key West. Local lore tells of Mrs. Sarah Orman sending warning signals from the captain's walk platform on the roof of the house to Confederate soldiers up river when Union troops were in the city. It is also reported that a brick outbuilding on the property served as a hospital during the war. The Ormans' only child, William Thomas, served in the 1st Florida Infantry as a lieutenant, and after the war as a state legislator and senator. Ironically, Thomas Orman was also arrested and detained by Confederate authorities on suspicion of Union sympathies at one point during the war when he traveled to Marianna, but was released after Governor John Milton intervened on his behalf.