The offices of the Caroline County Sheriff's Office are housed within the Caroline County Correctional Facility, located in Denton, Maryland. The original building (Center Portion) was constructed in 1906. Total capacity at that time was 24 inmates. In fact, in 1913 a prisoner was sentenced to death and hanged on these grounds.
In 1938 Sheriff William E. Andrew was elected and served for 23 years until his death in 1961. His son Louis Andrew completed his father's term and was officially elected as Sheriff in the next election. When Sheriff Louis Andrew began his term he had only one deputy. During these times the Sheriff and his family resided at the jail. There were no guards employed in the jail facility. During his 34 years as Sheriff his force grew to 17 Deputies.
In 1982 the East wing was erected creating 15 correctional officer positions. In 1996 the West wing was erected creating 11 more correctional officer positions. These additions increased inmate capacity to 142. Charles L. Andrew, the son of Sheriff Louis Andrew, later served as the "Superintendent of the Caroline County Corrections Department until 2008.
Sheriff Philip L. Brown began his term in January of 1995 at which time the Caroline County Corrections Department and the Caroline County Sheriff's Office became two separate entities. The Sheriff's Office today consists of administration, patrol, criminal investigations, narcotics, Canine, Court Security, Civil Process, Teen Court, and Records. Due to the expanding growth and needs of Caroline County, the Sheriff's Office is expected to grow exponentially to meet the citizens needs and call for service volume.