L-R: Key West Courthouse and Key West Jail in 1908
The 1892 jail had been specifically designed to mimic the Monroe County Courthouse, built just two years earlier. Both the jail and courthouse were considered impressive civic accomplishments, and symbols of Monroe County’s position as the most populous city in Florida at that time. Both were also built using red brick, although the front of the jail was later covered in stucco.
The 1892 jail was the fifth jail built at the Historic Jackson Square made from red brick. The first jail was built in 1828 and replaced in 1835. This process repeated itself in 1845, 1880 and 1892. In 1907, a 10-foot high concrete rear wall was built around the jail and in 1910 the jail was expanded to increase capacity with a two-story concrete cell block.
In 1952, the front of the old jail was demolished and replaced with a new jail and office for the Monroe County Sheriff. In 1965, the sheriff’s office was replaced with a courthouse annex. This annex was subsequently expanded in the 1980s. At that time, the north section of the 1907 wall was removed. Today, only the most rear portion of the 1892 building remains, including the entire 1910 addition and the 1910 cell block.
In 2017, Monroe County commissioned a full historical structure report which will be the basis for a $500,000 Historic Preservation Grant in 2018. If awarded, grant funding would become available in 2019 with work starting that fall.