Real estate

Historic Florida Keys ‘pirate-inspired’ home listing for $2 million – as owner warns area is losing its unique charm to faceless ‘concrete bunkers’

When Dubravka Wahl saw her unique home in Florida for the first time in 2023, she immediately fell in love. Not only with the prime beachfront location and double lot, but also with the unique pirate-inspired architecture that gave the property its signature Keys feel.

“It was absolutely beautiful,” she recalls of the $2 million home, which is conveniently located on Jolly Roger Drive. “I thought, ‘Wow, craftsmanship, a masterpiece.'”

However, upon further inspection of the property, Wahl was shocked by its abandoned condition. The Cudjoe Key home, which was completed in 1982, had not been updated in nearly 50 years and she remembers thinking what a “mess” it was, adding that it looked “so scary.”

But that didn’t scare her away; in fact, it only convinced her that she was the right person to take over the house.

It was that passion that ultimately secured her ownership; While many investors and developers flocked to the Keys in search of outdated homes they could tear down and replace with modern townhouses, Wahl saw something worth preserving.

22542 Jolly Roger Drive showcases classic Florida Keys architecture on a rare oceanfront double lot. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
The home’s unique pirate-inspired design stands out among the modern developments on the Florida Keys waterfront. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Concrete pile foundations protect the home from hurricane waves while preserving its historic architectural charm. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
A spacious living room with a cathedral ceiling offers ocean views and combines old Florida charm with modern upgrades. (REALTOR.COM)

“Everyone who made an offer wanted to tear it down because it sits on two lots, a total of 14,000 square feet, but the previous owner was heartbroken at that idea,” she explained.

“Her father, an architect from Massachusetts, built it as a vacation home in the early 1980s. She told me, “Whoever promises not to tear it down gets the house.” So I did that, and that’s why I got it.”

Wahl performed an extensive renovation, returning the home to its former glory and adapting it to modern Florida living. She even installed air conditioning, something the previous owner had surprisingly resisted.

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“Nothing needed to change structurally, but everything else was outdated,” she explained. “I installed new air conditioning and restored it respecting the original design. It is a house built for a subtropical environment… There are 8 meter high ceilings in the main room and even 5 meter high ceilings in the bathrooms, so the heat rises naturally.”

The original craftsmanship also ensures that the property will stand the test of time and withstand the ravages of the local climate.

“The amazing thing is it’s built with Florida wood, Dade pine and cedar, which is perfect for this climate,” Wahl added. “It has balconies, walkways and that beautiful bridge that connects the two upper bedrooms. It’s so charming.”

Now, in her later years, Wahl is selling the house, citing both personal reasons and a broader shift in a community she feels priced out of.

Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Custom kitchen with granite countertops and stainless steel appliances. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Charming balconies and walkways offer private ocean views and capture the home’s pirate-inspired design. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
The bright bedrooms have high ceilings and an airy layout, perfect for subtropical Florida living. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Built in 1982, the house had not been updated in nearly 50 years when the current owner, Dubravka Wahl, purchased it. (REALTOR.COM)

“When I first came to the Florida Keys almost 40 years ago, people were social. You visited neighbors, organized small festivals. Now people stay behind closed doors, entertained by their devices. You don’t even see kids playing outside anymore. The sense of community has really faded,” she said.

Wahl attributes this shift to the COVID-19 pandemic, when an influx of newcomers arrived in the Keys, changing the face of the community — both in aesthetics and feel.

“COVID changed everything. During the pandemic, people wanted to get out of the cities, and the Keys felt safe, they were just bridges connecting small islands,” she said.

“So people have discovered it. But now if you can afford to build a $5 or $6 million house here, you’re probably not working in the Keys; you’re in New York or Abu Dhabi. That’s who’s buying it now.”

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Rising property taxes have compounded the challenge for long-term residents — including Wahl, who said her home renovation has only increased her bills.

“When I bought this house, taxes were low because it was falling apart. Now that I’ve restored it, the tax man has tripled them,” she revealed. “It’s driving older people like me away. We’re on a fixed income, we can’t afford that.”

Property tax increases have become a major political issue in the state, with many residents struggling to keep up. That’s why politicians like Gov. Ron DeSantis proposed eliminating property taxes in the state earlier this year.

Just last week, the Florida House introduced a series of proposed constitutional amendments to reduce property taxes, including the DeSantis-backed idea to eliminate them altogether, which state residents will be able to vote on on the 2026 ballot.

Wahl, who is a fan of famous architects such as Frank Lloyd Wrightregrets that characteristic houses like hers are increasingly being replaced by modern ‘concrete bunkers’, as new residents with deep pockets move to the area.

Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Wahl said many potential buyers have seen the house as a teardown and have unveiled plans to build a brand new property on the oceanfront lot. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
The home sits on a coveted double plot, which makes it all the more attractive to developers. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
Wahl, a fan of famous architects like Frank Lloyd Wright, laments that characterful homes like hers are increasingly being replaced by modern “concrete bunkers” as new residents with deep pockets move to the area. (REALTOR.COM)
Historic 'pirate-inspired' Florida Keys home seeks buyer to maintain style while building 'faceless concrete structures'
“My message to buyers is simple: think again about demolishing. Add, renovate, expand – don’t destroy,” she urged. (REALTOR.COM)

“They are building what I call ‘concrete bunkers’: big, white, steel, square houses with no charm. They look like dentists’ offices. The architecture has lost its soul,” she said.

Although Wahl can no longer guarantee that the house will remain intact with its new owner, she hopes potential buyers will reconsider the demolition.

“My message to buyers is simple: think again about demolishing. Add, renovate, expand – don’t destroy,” she urged.

The home Wahl is selling, which is full of the pirate charm she loves, is on the market for $1.99 million — and is a rare oceanfront offering on the Lower Keys. Situated on nearly 0.16 acres (approximately 6,970 square meters) of waterfront land, it features four bedrooms and three bathrooms spread over approximately 2,440 square meters of living space.

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Built on concrete stilts in 1982, the property was completely renovated and can withstand waves and tides caused by hurricanes.

The home features high-performance doors and windows, new air conditioning, fresh floors and a custom kitchen with granite countertops and stainless steel appliances, combining modern systems with original architectural character.

The living and dining room with a cathedral ceiling opens via multiple sliders to an approximately 500-square-foot covered veranda, offering panoramic ocean views and a seamless indoor-outdoor lifestyle. The dual footprint and use of Dade pine and cedar provide both structural significance and lasting charm.

Although Wahl is sad to part with her pirate ship-inspired home, the sale offers an opportunity for a buyer to preserve a classic Old Florida Keys home in a prime oceanfront location.

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