The home features a number of custom murals, including an homage to ‘Jaws’ and musician Jimmy Buffett
THE SPECS
List price: $2.675 million
Size: 1,962 sq. ft.
3 bedrooms, 4 bathrooms
Land: .08 acre
Kerry Feigenbaum didn’t just want a vacation home in Key West—she wanted a unicorn.
Feigenbaum, 57, first visited the Florida island in 1984. Decades of vacations followed before she and her husband, Lyle Feigenbaum, 58, decided to buy. They had an ambitious list of must-haves: a central Old Town location, a driveway, a pool and a bathroom for every bedroom—all wrapped in historic Dade County pine.
“We had been trying to buy in Key West for a very long time,” says Kerry, who with her husband owns an Orangetheory fitness franchise in Bloomington, Ind. “It is our happy place, but we just had certain things we wanted.”
It all came together in March 2022, when the Feigenbaums paid $2.25 million for a home that dates back to 1908. It is on one of the island’s highest points—a low flood-risk zone—and directly across from the landmark cemetery, where a headstone quips, “I told you I was sick.”
The house’s exterior is a classic Key West green. Travis Yednak/Keys Property Visuals
Artist Haley Leeper painted a floral installation that climbs the main staircase. Travis Yednak/Keys Property Visuals
The house reflects the island’s history, which includes its past as a shipwrecking industry and reputation as a haven for creative people such as writers Tennessee Williams and Ernest Hemingway and musician Jimmy Buffett. Travis Yednak/Keys Property Visuals
A renovation opened up the floor plan. Travis Yednak/Keys Property Visuals
A classic Key West evolution
Like many of the island’s historic cottages, the home was a modest structure that grew over time through additions. While strict Old Town preservation rules protected the wooden facade, the Feigenbaums saw an opportunity to modernize the interior.
They spent roughly $350,000 on a renovation that gave priority to indoor-outdoor living. By updating the floor plan with french doors, they created an L-shaped layout where the kitchen, bar and living area spill onto the deck.
Floors are made of Dade County pine, which is prized for its strength and being naturally impervious to pests. Travis Yednak/Keys Property Visuals
The layout with french doors creates a natural flow for entertaining. Travis Yednak/Keys Property Visuals
Key West houses often have laundry outside, but the Feigenbaums moved theirs inside. They also tackled unsexy essentials, such as adding a new sewer line, pool pump and hurricane-impact windows and doors.
A residency in paradise
For 10 days, the couple turned their home over to Wyoming-based artist Haley Leeper. Living on-site, she created a series of custom murals.
There is a seaplane mural at the top of the staircase landing. Outside, near a coral-and-shell shower, another mural pays homage to ‘Jaws’ and musician Jimmy Buffett.
Travis Yednak/Keys Property Visuals
Can’t-miss feature
The property is home to a large mango tree that produces so much fruit, the couple spends their summers making mango daiquiris and sharing the harvest with neighbors.
The backyard is private because of a lack of two-story neighbors. Travis Yednak/Keys Property Visuals
If a piece of fruit falls into the pool, “it is like the best thing you’ve ever tasted,” says Kerry, noting that the soft landing and soak in the water somehow keeps the mangoes extra juicy.
Reason for selling?
A rare opportunity appeared two doors away: a historic “eyebrow” house, which is a classic Key West style where the roofline overshoots the upper windows.
The couple bought that house as a fixer-upper flip, but the renovation possibilities won them over. “We really don’t need two island properties,” Kerry says.
The couple had decorated the house with the intention of keeping it as their forever home. Travis Yednak/Keys Property Visuals
They will miss the home’s quietness because of its location across from the cemetery, plus how dark it got outside with the lack of streetlights. Travis Yednak/Keys Property Visuals
Market snapshot
Key West is a buyer’s market, says real-estate broker Brenda Donnelly, the property’s listing agent. She says inventory is up 10% from 2025 and the pandemic-era urgency has faded, allowing for more buyer leverage and due diligence. Typical buyers range from retirees to luxury investors who prioritize turnkey Old Town homes.
South of Miami, the Florida Keys are a chain of islands connected by 42 bridges stretching southwest from the mainland. Travis Yednak/Keys Property Visuals