Lewis H. Bailey (1818-1899) was a local banker, merchant, and hotel proprietor in Ridgefield, Connecticut. He had this stunning Italianate Villa home built on Main Street before the American Civil War. Bailey was savvy in realizing the upcoming development boom in town as wealthy New Yorkers began to arrive in town to build summer houses to escape the cramped city living and polluted air, and he began to sell off land and develop streets in the village. To house some shorter-term summer residents, Bailey constructed and operated the old Bailey Inn on a lot adjacent to his own home. The inn was torn down in the 1920s as the town’s dynamic as a summer town began to change with more more year-round residency. The Italianate Villa is a lasting legacy of Bailey and his impact on the town. The home with its square tower and detached carriage house are in a great state of preservation and significantly contribute to the character of Main Street.