January 24th-25th, 2025 Preview

Welcome to the 65th Annual Key West Home Tours, the longest-running home tours in the U.S.

This year's Tour takes place as we embark on the 65th anniversary of the founding of Old Island Restoration Foundation, established in 1960 as "progress" was taking place to tear down historic Key West buildings to replace them with easy-to-care for box and concrete block construction. OIRF is still thriving today, after ensuring that some of our greatest treasures were placed on the National Historic Register, and generations would continue to enjoy the largest predominantly wooden historic district in the United States!

About The Meadows

The Meadows is entirely residential and is criss-crossed with narrow, tree-shaded streets named Olivia, Georgia, Petronia, and Pearl. The Meadows is located west of Bayview Park, and is bordered by Eisenhower Drive, White Street, Truman Avenue, and Angela Street. Most homes in The Meadows date to the first decades of the 1900’s. Simple yet remarkably solid structures, they sit shoulder to shoulder, have weathered windstorm and fire, and offer personality personified. But - what’s with the name - "The Meadows?"

Early History
In the 1840s, the area was identified as Section 7 on a survey of the area, and, to the extent that it was not swamp, was mostly undeveloped grassland. Virtually all of Key West was concentrated way down near the harbor. As Army troops came to Key West, some of the last at the north side was used for barracks or a race track.

Dairy farm
In the early 1900s, the area was home to Cold's Dairy, a successful dairy farm. Maps dating from the mid 1880's show a prominent house, still standing, recently and beautifully restored, alone on White St. near the intersection of Olivia St. This was the Cold's family house and it stood virtually solo in The Meadows. Cold's Farm house stood alone on White St., dominating the dirt road that was the eastern boundary of Key West. Not another house shared the area. In the 1880s, 1890s, and early 1900s, block after block of The Meadows were uninhabited. The award-winning restoration of the house and grounds in 2006 - 2008 revealed numerous dairy artifacts and scores of bones of dairy cows.

So indeed, there was a dairy in The Meadows. Key West records show there were half a dozen dairies in Key West around the same period and continuing into the 1940s. These dairies were small, family-owned businesses where home delivery meant if you couldn't get to the dairy, the cow was walked to your door! A current show of the wood carving art of Mario Sanchez on display at the Custom House Museum contains a piece that shows a man walking his cow down the street, to deliver fresh milk to Key West residents before refrigeration.

Suburban development
But there weren’t houses in the meadows in the 1800’s. This original survey from 1847 by William Whitehead shows "The Meadows" area, below the Military Barracks and identified as “Section 7.” At that time, a detailed survey went only to the Old Town streets named Passover Lane and Angela St., streets just to the west and north (for us, the other side) of the cemetery, because hardly anyone lived outside of that area. At that time, behind the Military Barracks was shoreline and bay water. That entire area was now land dredged up during construction of the Florida East Coast Railway in the 1910’s.

In part due to the influx of cigar factory workers, and as land was filled by dredged fill, the Meadows gradually morphed from just pasture land to housing. By 1892 there existed a large cigar factory at the corner of Newton St. and White St. The factory had been there for a dozen years and, in the area were many homes for workers, a restaurant, and a bakery. This area, across from it on White St. and east along Newton St. towards the harbor, grew in populace and prosperity as cigars brought wealth and notoriety to Key West.

The cigar boom in Key West died away by the mid-1920s. Cigar manufacturers moved to Marti (outside Ocala, FL) and Ybor City, Tampa. Plus, cigarettes became more fashionable. The factory and all the surrounding buildings, 43 homes in all, on Newton, Angela, Ashe, and White Streets burned to the ground on March 20, 1923. At that time, the factory had been abandoned, and no cause for the fire was determined.

In the early 1900s, the Meadows was developed as a suburban neighborhood with wider streets and larger yards. It was a family neighborhood for working people, away from the tourists in downtown Key West. New houses were built with superior building materials and techniques using Dade County Pine, which is famous for resisting termites and rot (or, was famous until Floridians used it all up), and mortise and tenon joinery to provide a firm yet flexible structure.

The building date for many homes in the Meadows is shown on the county property records as "built in 1938,” but this is because there was a fire, which destroyed real estate records in the mid-30s, so the decision was made to just attribute all buildings as “1938” unless clear documentation existed to prove otherwise. Many of the Meadows homes are far older than this.

Sitting on a lot of land that was once the Cold Dairy Farm, 825 Georgia has been painstakingly restored by its owners. The approach that they took was a board-by-board approach to what was a true restoration – taking the house down to its studs and preserving many of the boards in their original location or re-purposed in another part of the home. Along the way, ceiling boards were uncovered that were actually crates used at the nearby Naval barracks. Those crate boards and much of the Dade County Pine remains.

Located at 610 Southard Street, the Benjamin Curry House is one of the few historic homes, still owned by the original family. This home was built by Benjamin Curry, Jr. the brother of Florida’s first millionaire, William Curry. The Currys emigrated from Green Turtle Cay, in the Bahamas to Key West, Florida sometime in the mid-1840s. They were loyalists who had moved to the Bahamas from South Carolina during the Revolutionary War.

Benjamin purchased an acre of land in 1855 to build the home, while the same day, his brother-in law Capt. John Lowe Jr. boughtt the property next door. The home at 610 Southard still has the doors, floors, windows and framework from when it was originally constructed. In the backyard, you can still find the original cistern and the double door, four seat outhouse.

Like many homes in Key West, it began as a simple one room cottage. As the Curry’s finances improved and the family grew, so did the house. They built the two story structure with a deep front porch facing the street. The one room cottage is now connected to the main house by a covered porch and a carriage house which was converted into a home which subsequent generations have occupied.

His grandson, Benjamin Curry Moreno was a city engineer and responsible for developing Key West’s modern roads and sidewalks. His only child was a daughter
Laura who was known as Betty. Betty was one of the artists that originally worked on the Mallory Square renovation. Betty also established the history department in the Key
West Library. She married Toby Bruce.

Some facts about the Bruces:

• Toby grew up in the same town as Hemingway’s wife, Pauline.
• Toby was brought to Key West by Ernest Hemingway.
• Toby was often referred to as Hemingway’s “man Friday”.
• Hemingway recruited Toby to come to Key West to help remodel his home.
• He not only built the brick wall around the home, but put in the first pool in Key West on the Hemingway property.
• He and Betty were his friends and even helped him purchase his home in Cuba.
• Toby served as a pall bearer at Hemingway’s funeral.
• Toby was a man of many talents. He designed and drew the dust cover for For Whom the Bell Tolls.

Betty had a history with Hemingway as well. She had met him years before when he rented a house across the street from this family home. As a child she had played with Hemingway’s oldest son, Jack.

On a Meadows Corner Lot sits a quaint, historic Victorian house, which draws you in with its large 443 sq. foot wrap-around front porch. It is possibly one of the in-town farmhouses present around the aptly-named Meadows. The work of its original owner as a sheep farmer is reflected in the wool spools which comprise the unique gingerbreading that draws the passer-by to its porch. Later owned by Key West short-story writer Colin Jameson, the home was sold to its current owners in 2011, who have retained many of the original features through a meticulous restoration.

This Historic Grand Dame is known for its stunning architecture and superb craftsmanship, including classic Dade County Pine, wrap-around porches, and a turret, as well as modern French doors and marble bathrooms. Outside, the back porch is a full living area, complete with a vertical garden loaded with orchids and more. The home also reflects a Who’s Who in Key West History.

Mr. (“Colonel”) Walter Cathcart Maloney Sr. was born in Darion GA in 1813, the son of a wealthy planter. His mother, a Cathcart, died while he was young and he was raised by a Catholic priest. He refused to run the family’s planation, being opposed to slavery, and chose to go to sea instead. He visited Key West in 1837 and stayed, making it his home for nearly 50 years.

Mr. Maloney Sr. was appointed Magistrate and Clerk of Monroe County in 1843-49 (at a time when Stephen R. Mallory was judge.) He then served as Marshall from 1849-53. Served as clerk to Asa Tift 1857-58. He served more than one term as mayor, served on several Courts Martial. He was a big proponent of bringing a railroad to Key West (for which he was called “insane.”) He was a lawyer and had served in the state legislature from Monroe County and as Mayor of Key West. During his time in the legislature, colored crews of ships were kept in jail while the ships were in port. He got a law passed to allow the crews to be bonded out by their captains. On July 4, 1876, - the first Centennial of Independence - he gave a speech about the history of Key West, which was later published as the first written history of the island, called “A Sketch of the History of Key West in 1876.” He died in 1884, at a time when he was the U.S. vice-consul for Sweden. He was extremely well-liked and esteemed in Key West.

Mr. Maloney had a number of children, one of whom was Walter Cathcart Maloney Jr. (1839-1894), who married Euphemia Bartlum (1847-1935) another of the oldest and most famous families of Key West. Her father was John Bartlum and her mother Sara Lowe Bartlum). Maloney Jr. is said in some records to have been a Union man. Most records say that he was in the Confederate Army. He was prosperous but not revered as his father.

In 1900, Harry L Knowles paid $650 to Euphemia Maloney, widow “in her own right” for the property – no mention of any buildings or other improvements on the property. Knowles is shown to have been paying taxes on it by 1906.

Harry Luther Knowles built and lived in the house until his death in 1944. Little is known about him. He had various occupations in Key West, none of them very well-paying, including multiple terms of service on the Navy police force and as a cigar maker. At one time Harry was a laborer for the WPA. There were many Knowles in Key West around the turn of the century.

Mr. Knowles lived at 1319 Olivia for over 40 years. In 1944, after Mr. Knowles death, the house was sold to Roger Watson, whose children resided there, until Mrs. Knowles sold it in 1972 to Mr and Mrs. James Heerin. A few years later it was sold to James Tripp, who owned until 2011, when it was purchased by Dan Bready.

If you have not visited The Oldest House in the last year, please take this opportunity to stop by and experience the exquisitely enhanced furnishings that have been added.

The last year has seen the addition of a fully restored 1825 New York DuBois & Stodart Piano, an empire clock & Federal style mirror in the Captain's Room along with period charts of shipping/ wrecking trade routes, an 1850's New England Child’s Rocking Horse in the girls' bedroom and 1840's English Bristol Blue glassware complimenting flow blue dinnerware identified from shards found onsite. The dining room is set for the last course/dessert of an English-style Christmas dinner.

The oldest house in southern Florida was originally located a block or two away on Whitehead Street. The Oldest House has weathered hurricanes, fires, and the harsh marine environment. Its resiliency is largely due to the skill of Captain Richard Cussans, a ship's carpenter who built the house. His mortise and tenon joinery, horizontal wall boards, and ventilation hatches or "scuttles'' have enabled the house to withstand the tests of time. The expansion of the city from its deep-water port beginnings was slowed by the existence of a natural salt-water pond that ran from Whitehead Street through the old city hall site to the port. By 1829 a large portion of the lake had been filled and the structure was moved to its current location. The house was enlarged to four rooms with a center hall to accommodate its next residents, Captain Francis Watlington, his wife Emeline, and their nine daughters. Captain Watlington held a number of maritime positions in his career including pilot, port warden, wrecker, Coastal Pilot for the U.S. Navy during the Second Seminole War, and the Inspector of Customs. One of his duties for the Customs Office was to oversee the "light ships," vessels that were used as floating lighthouses at dangerous coastal and reef locations. Captain Watlington served in the Florida House of Representatives from 1858 to 1861 only to resign his office at the outbreak of the Civil War. He joined the Confederate navy in Mobile Alabama and served as the captain of the gunboat Gaines of the Naval Squadron. With the Union victory in Mobile, Captain Watlington surrendered in May of 1865 and was paroled shortly after. He continued to live in Mobile after the war and did not return to live in The Oldest House until several years after his wife Emeline’s death in 1881.