Sitting in the vibrant district of historical Montgomery, the property that The Caroline House BnB sits on was granted a front yard plaque to inform those that pass by of its many years of history. Back in the 1850s, John E. Shelton, a master craftsman, purchased the land and existing buildings, where he then went on to build the main house for his friend and partner Thomas Wesley Smith, a cigar manufacturer. Smith and his heirs continued to own the property until 1924 when it was then sold to the Thomas A. Gay family. They owned it from 1924-1970 then sold to the Whisenant family from 1970-2000.
 
In 2000, Ms. Eckhart purchased the property and fully restored the home and buildings. She officially opened The Caroline House in 2006 as a Bed and Breakfast that the town allowing people from all over to continue to enjoy its historical charm.  In 2025 the property was sold to Eric and Connie Renouard who are continuing to preserve the charm and beauty of this beautiful Bed and Breakfast.