Old Town is the historic section of Key West in the downtown area. The Center of which is Duval Street, which is said to be the longest street in the US - running from the Gulf of Mexico to the Atlantic Ocean. The street is lined with many shops, restaurants, and bars with lively entertainment. This is where Key West began and grew to be the most populated and wealthiest city in Florida in 1876 when the cigar rolling industry and sponging were king. There is a lot of colorful history in these old streets. The rest of Key West did not develop until after World War II when, what is now known as New Town, was salt marshes that gradually were filled to create land for development.
The character and charm of Old Town have been painstakingly preserved in the largest residential historic district in the United States. Prices per square foot are some of the highest on the island, but the proximity of restaurants, entertainment, and shops within walking distance add to its desirability for part-time and long-term residents.
Truman Annex is both a neighborhood and military installation. Located west of Whitehead Street in the Old Town area. It is named after president Harry S Truman who had a winter home on the installation. The home is now a museum and known as the “Little White House” as he spent quite a bit of time there while in office.
The annex got its start in 1845 as part of Fort Zakory Taylor, a U.S. Army installation. The base was eventually taken over in 1947 as the "Fort Zachary Taylor Annex" to Naval Station Key West. New docks had been added in 1932 to make it a home base for submarines. The base was mostly decommissioned in 1974 because contemporary nuclear submarines were too large to use the facility. The Navy's primary installation in the area, Naval Air Station Key West, continues to operate about six miles up the Keys at Boca Chica.
Formerly the Truman Annex Naval Station, this award-winning, mixed use redevelopment sits on 45 acres in the heart of the Key West historic district. Between 1973 and 1977 the distressed surplus US Navy property was released to be managed by the Government Services Administration. The City of Key West created the Key West Urban Redevelopment Agency which was for 12 years unsuccessful in developing a master plan for the site.
In 1986 Pritam Singh purchased the 43-acre property from the GSA for a bid of $17 million and began the redevelopment initiative considered to be one of the most successful highly regulated and permitted real estate projects in Florida history.
This complex redevelopment project now known as Truman Annex, was completed in 1996 with 425 classic conch style, single family homes, high end condominiums a marina and a hotel. The adjoining Truman Waterfront was redeveloped by the City of Key West with sport fields, playgrounds, splash pad the Eco Discovery Center and Coffee Butler amphitheater.
Efforts were made to preserve the historic architecture in Key West in the 1970s. The Historic Architectural Review Committee, HARC, was put in place to protect the character of these buildings. Today, all new construction or alteration of existing buildings in the historic portion of Key West must first be approved by this committee of local volunteers.