Originally constructed speculatively for resale alongside the neighboring home (now a five-plex), Steele Cottage was built by two ambitious young Vicksburg attorneys, Sargent S. Prentiss and John I. Guion, who would later serve briefly as Mississippi’s 17th governor in 1851. When the homes did not sell, they were used as rental properties during a time when Vicksburg was booming with opportunity as the cotton industry began to flourish.

Shortly before the Civil War, the cottage was purchased by Francis Newell Steele as a home for his bride, Esther Rawson Steele. Legend has it that on their journey home, Mrs. Steele remarked she hoped he had not bought a two-story home — she did not want stairs. After Mr. Steele’s death just a few years following the war, she closed off the downstairs entirely. It remained unused for more than 90 years.

Steele Cottage also holds a remarkable distinction: it contains the only remaining indoor cistern in Vicksburg. During the approach of Union troops, Mrs. Steele and her servant lowered the family silver into the cistern’s water for safekeeping before leaving town. The valuables were successfully protected. During the Siege of Vicksburg, newspaper editor J.M. Swords and his family occupied a cave on the property, where he began writing a now-famous article later completed by Union soldiers after their entry into the city.

Harley Caldwell’s late mother, Mary Lou Halpin, grew up at what is now Anchuca Mansion and Inn. She would walk past Steele Cottage on her way to the “sisters’ school,” now the Southern Cultural Heritage buildings. She used to say to her friends, “When I grow up, I am going to live in that house.”

The last Steele grandchild died when Harley was three. The upstairs and downstairs were not connected, and the Halpins eventually passed on purchasing due to the major renovations that were needed. The home came up for sale again when Harley was 20. By then, a staircase had been added along with a downstairs kitchen. Her parents didn’t even come back for a second look — they bought it immediately.

Shortly after Jack Halpin’s death in 1984, the Caldwells came to spend six weeks with her mother while they closed on their new home. Harley enjoyed living with her mother and had a great life until she couldn’t live with her mother any longer.

Mae-Mae eventually moved and the Caldwell's have been working on Steele Cottage ever since. When Harley and Rick purchased the Duff Green Mansion in 2015, the Caldwell children asked their parents not to sell Steele Cottage, where they had grown up. The children did not include any money with the request.

The transformation into a guest home was easy — just one door at the bottom of the steps. The Caldwells and their dachshund, Sarah Bailey, live downstairs.