This building was constructed around 1847-1850. The left portion of the building with the Mansard roof was originally built to store natural ice, which arrived in special ships from New England. In recent history, this portion of the building has been used to house the sponge market. The right portion of the building was originally a chandlery for Tift and Company, who were agents for the Clyde and Mallory Steamship Lines. It also served as the island's Post Office from 1847 until the Civil War. In recent history, this portion of the building was used as the Key West Chamber of Commerce.

This building was constructed around 1850 and originally served as Tift and Company's warehouse storage. In 1960, the Key West Players, a local theater group, found a home in this warehouse with the help of fellow Player, Tennessee Williams. The Key West Players completely restored the building and converted it into a modern, functional playhouse for their use. The building and theatre group then became known as the Waterfront Playhouse, which is considered the oldest continuously running theatre group in Florida today.

Two stone cisterns were constructed in this area around 1870 and were used to store fresh water for visiting ships. One cistern, which was located to the south of Waterfront Playhouse, has since been converted into public restrooms. The second cistern, which was located to the north of the Waterfront Playhouse, was converted into a walled garden in the 1960s and is now used as an event space by Meson de Pepe.

This building was constructed as a warehouse in 1879 by descendants of William H. Wall, who was shipwrecked in Key West in 1824 and decided to make the island his home. He became the first Key Wester to own a cigar factory in 1931 and was a pioneer in the industry until his death in 1866. The Wall and Company warehouse was first owned by Asa Tift, who was considered to be the most notable salvager in Key West at the time, and who used the building as storage for his wrecking business. It was later used as a convention center for the City of Key West and hosted many public events. Today, the building is home to the restaurant Meson de Pepe.

This building is an example of Old Key West architecture. It was built after the Great Fire in 1886 and was originally used as a ticket office for passenger and freight service by Tift and Company. In the 1960s, the building was relocated from its original site and restored. It was then used as the headquarters for the Old Island Restoration Foundation and as a hospitality center for welcoming visitors to Key West.

This frame building was originally constructed in 1853 for use as a grocery store, which was owned and operated by George Babcock. The Great Fire of 1886 seriously damaged the building, and so it was rebuilt as a one-story building, with the second story added in 1906. In 1935, it became the first art gallery to exhibit artwork to the public in Key West. It was one of the first buildings to be restored in the Mallory Square area, and it became home of the Key West Art Center and Gallery in 1960. Today, it remains an art center that is open to the public.

These octagonal concrete structures were built to store cable, which was used for communications between Key West, the West Indies and South America. The first cable connecting Key West with Cuba and Florida's mainland was begun to be laid in 1867. The Eastern cable hut was constructed in 1921, while the Western hut was constructed later in 1932. Today, the structures are in the process of stabilization.

The Key West Aquarium began construction in 1933 and was opened to the public in 1935. The Key West Aquarium was the first aquarium to use an "open air concept," which allowed natural light to shine onto the marine displays from above. During World War II, the U.S. Navy, Marines and Coast Guard used the aquarium space as a rifle range. In 1946, the building was returned to the City of Key West and was restored to be used again as an aquarium. In the 1960s, the addition of the roof brought an end to the open air concept. The aquarium is still in use today.