James McDearmon owned Mount Evergreen, an estate originating in the land bounty granted to his grandfather for French & Indian War service.

[6] This property was about seven miles (11 km) southeast of Clover Hill (later known as Appomattox Court House village).

In August 1845 he had borrowed over two thousand dollars from his uncle Samuel J. Daniel (1787–1850) to invest in Clover Hill real estate, and thus began to play a critical role in the development of the village of Clover Hill (after 1845 officially Appomattox Court House), where Robert E. Lee surrendered to Ulysses S. Grant on April 9, 1865.

In 1851 McDearmon built the Union Academy and Hall ($1100) on a 1-acre (4,000 m2) lot carved from his Clover Hill tract.

In 1851 McDearmon was elected to serve in the Virginia State Senate 1852-1854, representing Appomattox, Campbell and Lynchburg City after a tumultuous race.

[12] Also during these heady days McDearmon had striven mightily to promote the Southside Railroad (Virginia) as a boon to the new county (and himself).

Whatever the ultimate success of his various ventures McDearmon had begun to develop business relationships in a wider field.

William C. Flournoy, delegate from Prince Edward 1850-1853[17] had been his partner in the High Bridge masonry contract.

In 1852 he partnered with fellow southside Virginians as McDearmon, Scott & Booker commission merchants in Richmond.

Wise for the governorship in 1855 produced an appointment at Richmond's Shockoe warehouse as tobacco inspector, an office of historic although declining importance in the commonwealth.

[1] Following the defeat of Wise's forces in 1861 McDearmon limited his service to providing the army with lumber and other essential supplies.

McDearmon had sufficiently recouped his fortunes to declare 600 acres (2.4 km2) worth $8000 in the county by the agricultural census for that year.