This impressive residence beckons back to the sounds of shipbuilder’s tools, a slower time, and memories of a long line of island leaders. Shipbuilder Samuel Filer built the structure featuring heavily bracketed double porches in 1865. He chose Dade County heart pine as the primary building material knowing that the wood is highly resistant to termites and sub-tropical weather. It proved to be an excellent location to raise his four children.The house has been sold only one time, in 1920, to Monroe County Commissioner T. Jenkins Curry and his wife Louise Thompson. Both were born in the Bahamas to families who had received land grants there from the King of England in recognition of their Loyalist patriotism in the Carolinas during the Revolutionary War.In the 1920s, the Curry’s renovated the house first by moving it forty feet towards the back of the lot using large rolling logs, teams of mules, and a windlass connected to a large banyan tree in the backyard as anchor.Further upgrades came with a new kitchen and bathroom featuring running water. Previously these facilities had occupied separate buildings in the back yard. As gas illumination declined and electric power became accessible, electric lights were installed throughout the house.The famous Cuban-American artist Joaquin Barroso was commissioned to paint the walls of the double parlor with landscapes and scenes from the owner’s life followed by the installation of a large pool table. The Curry’s entertained in grand style.The Curry’s were divorced in the early 1930s. After deeding the house to Louise and converting it into a rooming house, Jenkins left to live in Key Largo where he dealt in real estate and co-founded the Florida Keys Electric Cooperative.Louise operated the prosperous rooming house during the 1930s. She was famous for her meals. Winter rates were $3 per day or $15 per week.A few years later, Jenkins suffered a stroke and returned to Key West. Louise and his two devoted daughters cared for him until his death in 1958.Jenkins and Louise’s daughter, Mary Eloise, married William A. Freeman, a third generation Conch. His mother was from a prominent Baltimore family which included Wallis Simpson, the Duchess of Windsor.William served on the Key West City Council and was instrumental in the city buying City Electric. City Electric was created by the merger of three competitive electric companies. The Acquisition brought standardized electric service to the island and expanded power service to the outskirts of town.The couple raised their two sons, William Jr. and David in the house. William Jr. went on to serve as Monroe County Commissioner, Florida State Representative and Sheriff of Monroe County.