Gillespie House is located at 237 North Oak Street. The house was built around the turn-of-the century and is a classic example of Victorian architecture.

The house was named for Cade Drew Gillespie Sr. who joined with the Raymond Fencibles in 1861. During the battle of Frazier Farm in Virginia, he was severely injured in the leg, a wound from which he never fully recovered. In spite of his injury he remained with the regiment until 1864. After returning home, he resumed his law practice in Raymond.

In 1883, Cade met and married Carrie Blanche Johnson who was visiting from Lafayette, Georgia. The marriage was a brief one, lasting only ten years. In 1894, Cade died at home from the leg wound he sustained during the war. In the years that followed, Carrie became a charter member of the N. B. Forrest Chapter of the UDC in Raymond where she worked tirelessly to organize the placement of markers at the Confederate Cemetery.

She also worked to secure the Confederate Monument that now adorns the Courthouse grounds. “When my grandmother Carrie died,” Martha commented, “I found letters, papers, clothes, and memorabilia preserved in her trunk. One of the papers was the order for 70 markers (headstones) for the Raymond Confederate Cemetery.” Martha is the third generation Gillespie to live in the family home.