1
Captain George Carey House
The two story, double portico building is the second oldest house in KeyWest. Originally built as a two room house in 1834 by British Captain Carey, who made his money in the whole-sale liquor business. Enlarged in 1844 as a gift to his bride. Robert Frost spent 16 fruitful winters in the writers' cottage located in the gardens behind the house.
2
The Key West Woman's Club
Built by Captain Hellings who was the manager of the International Ocean Telegraph Co. His wife was the daughter of William Curry, Florida’s first millionaire. The Key West Woman’s Club purchased the home in 1940 and operated one half of the house as the only public library in Monroe County.
The carriage house behind the building is home to the Red Barn Theatre.
3
The Oldest House
Originally a four room house built on Whitehead Street in the late 1820’s by Richard Cussans a ship’s carpenter. The structure was moved to its current location in 1829 and expanded for Captain Francis Watlington to accommodate his wife and nine daughters. The Captain’s descendants lived in the house until the 1970’s. This is considered the oldest house in South Florida.
4
Dr. Joseph Yates Porter House
Built as a two story house and later expanded with a rare third story mansard roof with gabled dormers. Dr. Porter was born here in 1847 and died in the room of his birth 80 years later. Dr. Porter was Florida’s first Public Health Officer. His medical research and involvement in yellow fever epidemics is credited with the eradication of yellow fever in Florida.
5
James Haskins House
The fire of 1886 missed this single family house by 20 feet.
A portion of the first floor was rebuilt at street level in 1889 for a “Gents Goods†store. The storefront saw a succession of commercial uses through the years and the house became a boarding house in the early 1900’s.
Restored in 1987 and enlarged in 1993 with the addition of two neighboring historic buildings.
6
Casa Antigua
The Trev-Mor Hotel, one of Key West’s first hotels. Built with bricks from Fort Taylor dating back to 1845. It featured a car dealership on the first floor and hotel rooms on the upper two floors.
Ernest Hemingway and his wife stayed here in 1928 and penned "A Farewell to Arms" from his second story room.
The hotel was converted to a private residence and renamed Casa Antigua in 1978.
7
The Oldest Drug Store
This building holds the dual distinction of being one of the oldest commercial structures in Key West and the oldest remaining drug store building. Dr. John Maloney opened the Key West Drug Company in 1903.
In 1908 he purchased the adjacent building at 532 Fleming and opened the first public hospital. In 1911 he acquired 504 Simonton connecting the buildings with a raised walkway .
8
The Southernmost House
Built in 1897 by Judge Vinning Harris and his wife Florida Curry. The Queen Anne Victorian style mansion was designed as a one bedroom home. Thomas Edison oversaw the homes electrical design and installation. During Prohibition the mansion served as a “speakeasy†club and in the 1940’s a night club called “Café Cayo Huesoâ€. Five United States Presidents have been hosted at the mansion.
9
Fire Station No. 3
Believed to be the oldest active fire station in the State of Florida until 1998. Started with 3 paid employees and 40 volunteers it featured horse drawn steam engines and hose carriages. The station switched to motorized fire engines in 1914. The horse stalls were removed and a concrete hose trough was added behind the building in the 1940’s.
10
Key West Armory
The Armory was in such an advanced state of deterioration by 1969 that the State granted the City permission for it’s demolition. Joseph Allen and State Representative William Roberts fought to save the building and were instrumental in forming the Historic Preservation Board. Preservationists James Shields, Edward & Joan Knight, Larry Nettler, Mary Lee Graham and Norman Artman are also credited with preserving the structure.