David W. Wolkowsky

David Wolkowsky is an American developer from Key West, Florida, United States.

His grandfather, Abraham Wolkowsky, moved to Key West in the late 1880s and established a fine clothing store on Duval Street. The late Edna Wolkowsky was his sister. His other sister, Dr. Ruth W. Greenfield, is the prominent Miami musician and social activist. His nephew is the photographer and filmmaker Timothy Greenfield-Sanders.

David Wolkowsky grew up in Key West and Miami and received his degree from the University of Pennsylvania. After college, he began to restore buildings in the inner city of Philadelphia. He is credited with starting the rejuvenation of Society Hill and Rittenhouse Square in that city.

Wolkowsky visited Key West in late 1962, after the death of his father, Isaac Wolkowsky. The family had a few properties in "old town" Key West and Wolkowsky decided to "retire" to Key West at the age of 40. Unable to sit still, he rescued a condemned bar on family land on Greene Street, which was the original home of "Sloppy Joe's" of Hemingway fame. From there he developed property on lower Duval and Front Streets including "Pirate's Alley" and the "Original Cigar Factory". In 1963, Wolkowsky accomplished a major real estate coup by purchasing, for $106,000, the old Cuban Ferry Dock, choice waterfront property near Mallory Square.

Wolkowsky lifted the 1890 Porter Steamship office off its foundation and moved it 300 feet (91 m) out, setting it on pilings in 40 feet (12 m) of water. He transformed the Steamship office into "Tony's Fish Market", a restaurant and cocktail lounge where guests could watch shrimp boats in the channel on their way into port. He is credited with putting Key West on the road to being a major tourist destination.

In 1967 Wolkowsky hired architect Yiannis B. Antonidis to help design a motel around the restaurant, with 50 unique rooms, to which 50 more rooms that faced the ocean were quickly added. The completed structure was christened "Pier House Resort Motel". Both Jimmy Buffett and Bob Marley started their careers in the hotel's funky "Chart Room Bar". Buffett credits Wolkowsky as the first to hire him.

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