1926 – A delegation appointed by the Monroe County Commission traveled to the Matecumbe Keys to help find the best route through those islands for a new highway. Some Matecumbe residents feared land values would plummet if the planned road traversed their properties, and the delegates hoped to ease their minds.

1976 – Windsor Village Condominiums, a one-acre tract with 11 houses and fronted by Windsor Lane, was established as a Key West literary compound. Writers John Hersey, Ralph Ellison, John Ciardi, and Richard Wilbur made the first purchases.

1938 – After two years of discussion and planning, the Key West City Council passed an ordinance providing for zoning within city limits.