Old Town Key West’s Most Famous Historic Homes

It seems like around every corner in Old Town Key West you’ll find a Historic Home where someone famous lived, visited or something of historical significance took place. Key West has the largest historic district on the National Register of Historic Places. Most of the wooden houses and structures Old Town is famous for, date from the late 1800’s and early 20th Century, and range from cigar maker’s cottages to millionaire’s estates. In the 1970’s, people began renovated them and Old Town officially became a historic district.

Hemingway house Key WestProbably the most famous historic home in all of Key West is the Ernest Hemingway Home located at 907 Whitehead Street. The home was built in 1851 by a maritime salvage wrecker named Asa Tift. Ernest Hemingway resided in the home for 10 years beginning in 1931. One of the most well know features of this home is the resident six-toed cats. There are 40-50 of these cats on the property, descendants from Hemingway’s six-toed cat, Snow White.




oldest house key west

At 322 Duval St stands the “Oldest House”. Richard Cussans is credited with building this house about 1829 on Whitehead Street (Duval Street did not exist at the time). By 1836 the house was moved to its current location. It was the home of Captain Francis Watlington, his wife Emeline, and nine daughters. More information about the Oldest House here. 






audubon house key west

The Audubon House, also known as the Geiger house, at 205 Whitehead St., was home to Captain John Geiger and his family for over 120 years. In 1960, it was saved from demolition an opened as a museum in honor of John James Audubon. Though he never lived in the house, he visited Key West in 1832 and discovered 19 new species of birds here. More information about the Audubon House here





Harry S. Truman Little White House Museum

Florida’s only presidential home site is the Harry S. Truman Little White House at 111 Front St. Originally constructed by the Navy in 1890, it was transformed into a vacation home for President Truman in 1948. More information about the Little White House here.






Heritage House and Robert Frost Cottage

The famous poet, Robert Frost, visited Key West between 1940-1960 and stayed with Jessie Porter (A 5th generation of early Key West settlers) at her home at 410 Caroline St.  Captain George Carey is credited with building the original home in 1834. The home, now known as the Key West Heritage House Museum and Robert Frost Cottage was a museum for many years but now is a rental property.






tennessee williams homeFamous playwright and author Tennessee Williams resided in Key West for 34 years until his death in 1983. The home where he lived for many of his years in Key West is located at 1431 Duncan Street and is now a private residence. “A Streetcar Named Desire”, “Cat on a Hot Tin Roof” and “The Glass Menagerie” are among his most well-know works. The Tennessee Williams in Key West exhibit is a museum at 513 Truman Avenue to honor this famous writer.





Key West Womens Club

Brick was rarely used in the early homes of settlers, but at 319 Duval St. stands a brick home built by the Captain Martin Hellings, the manager of the International Ocean Telegraph Company in 1892. It was home to The first public library in South Florida and now houses the Key West Woman’s Club. The Red Barn Theater resides in the structure that was the original carriage house.





Artist's House

The Artist’s House at 534 Eaton St. is a beautiful Victorian home built by Thomas Osgood Otto in the 1890s. His son, Eugene Otto was a famous artist and used the turret of the house as his art studio. More well know is Eugene’s haunted childhood doll, Robert, who now resides in the Fort East Martello Museum.







Donkey Milk HouseThe first thing you’ll notice at 613 Eaton St. is an enormous clay pot in the front yard. This is a Cuban “tinajone,” and was used to collect rainwater.  This home was built in 1866 by Peter Williams and stayed in the family for 120 years. Behind the home is Donkey Milk Alley, created so the milkmen could deliver on their carts pulled by donkeys.






For a more extensive list of famous historic homes, visit the Old Island Restoration Foundation’s website and the Key West walking tour guide.

Start your Search for an Old Town Key West Home here!! Or call Sean at 305-924-0700 for assistance finding the perfect Old Town Key West Home!