For a while, the thing rising out of the sand on Gulf of Mexico Drive didn’t look like someone’s beach house. It looked—depending on your tolerance for large-scale residential ambition—like a boutique hotel or the early stages of a pricey misunderstanding.

Jim Holanda heard the chatter. “I know a lot of my neighbors and people around town thought that it was like a small hotel that was going up,” he says. “It looked so grand when it was just concrete posts.”

The concrete posts belong to 5965 Gulf of Mexico Drive, Gulf-front estate on Longboat Key that's currently under construction—and now listed for $38.45 million.

According to current single-family listings in Sarasota and Manatee counties, that makes it the priciest home on the market. The next-highest active listings, both on Siesta Key, are priced at $29.995 million.

In other words, this isn’t a shy house.

If it sells near its asking price, it would also clear the region’s current residential sales record: the $30.3 million cash sale of Serenissima, the Venetian-style estate at 845 Longboat Club Road that closed last year. 

When completed, the property will have 11 bedrooms, 17 bathrooms and 17,199 square feet of living area across a main house, guest house and pool house. It sits on almost two Gulf-front acres and includes a pool and spa, rooftop deck, dual kitchens, wine cellar, private cinema, elevator, split garage, golf cart parking and room for the kind of family gathering that doesn’t end after dessert.

But the funny thing about the most expensive house on the market is that it wasn’t conceived as a market object at all. It wasn’t built as a spec mansion nor as a trophy listing in search of a trophy buyer. It was supposed to be Jim and Amanda Holanda’s dream house. 

The Holandas bought the property in 2021 for $10.15 million. At the time, there was already a very large house on the site: a Mediterranean-style estate built in 2007, with six bedrooms, five-and-a-half bathrooms, a pool and more than 10,000 square feet of living area. In most neighborhoods, that would be the big house. On this stretch of Longboat Key, it has become the "before" picture.

Holanda knew the area long before he bought here. His grandmother wintered in Palmetto for decades and later lived there full time. His aunt and uncle lived in Ellenton. As a kid, he knew the local circuit: Siesta Key, St. Armands Circle, the Ringling Museum, and even “Snooty the manatee in Bradenton,” he says.

He and Amanda, known as Mandy, who grew up in Northern Ireland, considered Scottsdale, Arizona, as well as the Sarasota, Naples and Fort Myers area, when they first started looking for a vacation home. Longboat Key won.

“As soon as she saw St. Armands Circle and Longboat Key and the country club there,” Jim says, “it was just a great fit.”

About seven or eight years ago, they bought a bayfront house in Country Club Shores. They joined the Longboat Key Club. They settled into the particular Longboat rhythm of beach, bay, golf, tennis, pickleball, restaurants and the pleasing reality that one can somehow be secluded and social at the same time.

Then they bought the Gulf-front house. “Two acres on the beach,” Jim says. “Who gets that in this day and age?”

At first, the Holandas didn’t plan to start over. They had renovated the bayfront house with Bluewater Construction and Sweet Sparkman Architecture & Interiors, and were considering what to do with the beach house. One option was a roughly $1.5 million renovation. Another was a much larger redo. Then the builder came back with a third possibility: for about 10 percent more, they could tear the house down and build new, bringing the property up to newer coastal standards and giving the design team a chance to rethink the site itself.

That changed the conversation.

The new house has a very different attitude than the one it replaced. The old estate was formal Mediterranean, all arches and stucco and grand staircase. The new one is cleaner, lower and more contemporary, with broad rooflines, concrete construction and a coastal style Jim describes as “coastal California, coastal Florida.”

The look, he says, came largely from Mandy. “She knew exactly what she wanted,” he says. That makes sense, because the house has a family nickname: Mandy Land South.

“We have a Mandy Land North in New Jersey,” Jim says. The Longboat property would be the southern version.

For all its scale and concrete and price-per-square-foot mathematics, the place was imagined as a landing pad. Jim and Mandy have been together for 35 years. They have three grown daughters. Earlier in their marriage, Jim’s career had them moving—nine times in the first 14 years, he says, as they crisscrossed the country for work. Longboat Key was supposed to be where everyone could come back together.

“Mandy Land is where you go to decompress and have fun,” Jim says. “My wife’s usually at the center of all of that.”

That idea drove the layout. The house was designed for a large, loose, multigenerational crowd: relatives, friends, daughters, partners, guests coming in from Ireland, Southern California, the Midwest and wherever else life had scattered people. Jim says the home was meant to work for 20 or 30 people at a time, with spaces to gather and enough separation that no one had to be together every minute.

Plus, there are those views. “The entire estate was designed to maximize views of the ocean and the sunsets,” he says, as well as sunrises over the bay. 

Jim had spent the last 15 years as CEO of Astound Broadband and its predecessors, based in Princeton, New Jersey. When Astound moved toward a merger with Google Fiber, he expected that transition to give him more flexibility. Instead, another job came along. Last summer, he became CEO of Cable One, a Phoenix-based company.

The Holandas know Arizona well. They met in Southern California and spent time in Phoenix and Scottsdale early in their marriage. Cable One meant Jim would need to spend more time in Arizona, and the Longboat plan began to wobble.

“We had to make the difficult decision to put the beach house up for sale,” he says, “just because we’re not going to be able to use it the way we originally envisioned it.”

That's how a dream house becomes a listing before the owners move in.

Jim says the asking price is meant to recoup the original purchase price, plus what the Holandas are putting into the build. He also says the budget changed. The project unfolded through post-pandemic supply-chain problems, inflation, labor and materials escalation, and the general modern experience of trying to build anything ambitious in coastal Florida without watching the number climb.

“When we originally set out, it was a different budget than what we ended up doing,” he says. “But again, because it was our dream home, we didn’t want to lose steam.”

Compared with the California, Naples and markets on Florida's east coast, Jim says, nearly two acres on the Gulf with three structures, a large pool, a tennis court and parking for 18 cars can look almost rational. (This is the part of luxury real estate where language starts to bend.)

The likely buyer, he says, could come from several directions: wealthy Californians or New Yorkers weighing Florida as an option, retirees looking for a final dream home, or families like his own who want a second home that could eventually become a permanent one.

The house is expected to take another 10 to 14 months to finish, according to Jim’s builder’s estimate. The Holandas sold their bayfront home last July.

Still, he talks about Longboat Key with affection. Even after 2024's hurricanes complicated their time there—Milton damaged docks and landscaping at the bayfront house, though the structure itself was OK—he says the island kept its appeal. He mentions not just the beach and the club, but the people.

“Regardless of whether you’re in the mobile home park or you’re in a high-rise condo or you’re in an old shack on the bay with a fishing boat or you’re on the beach, we found people to be just very down to earth and kind,” he says.

Interested? Call Joel Schemmel of Douglas Elliman Real Estate at (941) 587-4894.