Key West is one of Florida's most historic cities; as such there are tons of homes steeped in history that every lover of classic architecture will adore. All of the homes on this list were built before 1930 and are located in Key West. The rest of the keys don't have many homes from this period. This list is ordered from the least expensive to the most, but be prepared: any Key West home comes with a hefty price tag. The lowest cost home on this list is $899,000, and all the rest of the homes come in at over $1million.
Year Built: 1918
This home is a great purchase for someone who wants to work and live in one place with a price tag that is just about the best you can do in Key West. The downstairs is set up as a commercial unit with 1 full bath and a half bath, and the upstairs has one bedroom and one bathroom. It also contains a large, unfinished attic that could make excellent extra space for someone who wants to spend time on it. The house was built in 1918 and was most recently updated in 1997.
Year Built: 1889
Live the true Key West lifestyle in this traditional Conch Cottage located in the Historic District. It has plenty of outdoor space to enjoy the Florida sunshine as well as 3 bedrooms and 2 bathrooms. The house was built in 1889 with the last major renovations in 1997.
Year Built: 1928
This house is located right in the middle of the action only a block away from the Southernmost Point. Living here means being right on the side of the ocean while also being next to plenty of places to eat, shop, and be entertained. It was built in 1928 and still contains so much of what was traditional to that era, but with extensive renovations done in 2016, you get tons of modern comforts too.
Year Built: 1909
This home has the advantage of being in a quiet part of this exciting island without being too far away from the action. It was built in 1909, but completely renovated in 2003, with even more extra features added in recent years so you can have every comfort the modern age has to offer.
Year Built: 1926
This house is one of 6 original Spanish revival style homes built by a Coral Gables builder in 1926. It is a gorgeous piece of Key West history, but is unique in style from the traditional island homes. It has three bedrooms, all en-suite; two kitchens; and tons of indoor and outdoor space in one story.
Year Built: 1929 (possibly older)
This tropical island home is steeped in history. Zillow lists it as being built in 1929, but the description claims that it was actually built in the 1800s. It was reportedly built by Odet Philippe, who was known for bringing cigars and grapefruit to the Tampa Bay area. Before heading to Tampa, he lived in Key West, where some believe that he worked with pirate John Gomez to smuggle slaves. The house is known locally as the Pirate House for its seafaring history. It is a classic Victorian style home with 6 bedrooms, 6 bathrooms, and a beautiful pool, so you get tons of comfort in addition to the history.
Year Built: 1893
Get three for the price of one with this lovely property. It includes 3 lots with two houses and one empty lot for room to expand. The main home was built in 1893 and the second house was built in 1905, so you will find tons of history in both homes.
Year Built: 1907
This cute island home is located in the perfect neighborhood in old town Key West. It was built in 1907 by William Kennedy, the designer of the Curry Mansion and is known as The House of Seven Gables. It was expertly renovated in 2004 and is an exquisite ceramic star winning historic renovation.
Year Built: 1892
Be right in the center of Key West with this historic home located on Duval Street, Key West's most famous street. It is a transient licensed home offering great income and expert management, so you can work where you live. With 6 bedrooms, 7 bathrooms, and a beautiful pool, it offers a wonderful way to live your best Florida life.
Year Built: 1865
You will truly be a part of Key West history if you purchase this home. The Curry-Freeman House, as it is locally known, was built circa 1865 and is one of the oldest private homes on the island. It was built by a prosperous seafaring merchant and ship-builder during the time when Key West was one of the richest cities in the country. Since then it is has been home to many politicians and other public figures. In addition to the history, the home also has tons of space. It is located on a third of an acre with a 3 bedroom / 3 bath main house and a carriage house that has 3 private apartments. There is a private museum located in the garage.