The 1917 Courthouse stands on the footprint of the first Chesterfield County courthouse built in 1749 and demolished in 1917, against the will of local citizenry. This early preservation case was the subject of heated debate between concerned citizens wanting to save the historic courthouse by building a new one in Chester, and prominent residents led by county supervisor Walter A. Horner who argued successfully to retain the courthouse at its original location. The cornerstone of the new Courthouse was laid on October 26, 1917 during the annual county fair and was followed by a parade of one hundred drafted men encamped in the courthouse yard. On February 5, 1917, a contract was awarded to Vaughan Construction of Shawsville, VA, for a new brick building measuring 48 by 84 feet. An all-day picnic was held on May 2, 1918 when the doors of the new courthouse were thrown open for the first time. All schools were dismissed and pupils were thrown open for the first time. All schools were dismissed and pupils were urged to take part in the festive program. The first term of court opened in the new courthouse on May 13, 1918 when Judge Robert G. Southall took the bench.
The original Chesterfield County Courthouse was built in 1749 and was used until 1781 when it was burned by British troops under the command of Gen. William Phillips.
It was rebuilt by 1783 and was used until it was torn down to make room for the new courthouse in 1917.