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As a professional gambler, Billy Walters built his fortune winning at a game few have mastered: the high-stakes, high-risk world of multimillion-dollar sports betting. In a good year, he can rake in as much as $15 million from gambling, and he claims he’s never had a losing year.

But when it comes to residential real estate, Mr. Walters, 64, claimed his track record has been far less lucrative. “We’ve lost money on every home we’ve bought and sold here,” he said. “It’s not what I do for a living. If it was, I’d be in trouble.”

He said that he’s likely to continue his losing streak, recently listing his Carlsbad home—one of seven he owns with his wife, Susan—for $29 million, a bit less than he spent assembling it. Situated on a quiet surfing beach, it’s one of eight homes the couple has owned in the area over the years. The couple said they’re selling partly because Susan, who oversees interior design for all their homes, is ready for a new project.

The Walterses’ five-bedroom, nine-bathroom home is currently the priciest home on the market in this sleepy, oceanfront town about a half hour north of San Diego. Brian Guiltinan, a local broker, said that while high-end sales have improved dramatically in the past few months, only six homes have ever sold in San Diego County for more than $20 million. But Mr. Walters’s home “is really unique in the area, which makes it tough to put a price tag on.” (Listing agent Doug Harwood said the home is priced to sell.)

Built mostly of Senora gold limestone, the 10,000-square-foot home sits on an acre and a half, its gated entry separating it from the beach traffic outside. With its large windows overlooking the ocean, curved palm trees lining the back patio, lush landscaping and lava rock fire pits, it has an ocean-themed, slightly Hawaiian vibe.

The interior is contemporary with lots of custom finishes, from antique Douglas fir beam vaulted ceilings to hand-blown glass sculptures. Couches, chairs and pillows in creams, beiges and sea foam colors fill the two-story living room.

There are many of the trappings found in modern trophy homes: a movie theater, an 1,800-square-foot guesthouse and a television that rises from the foot of a bed. But some details are unique, like the poker room with a large marble bar. And like all of the couple’s homes, it has two master suites. The Walterses, who have been married almost 35 years, said they started the arrangement when Mr. Walters was playing professional poker and coming and going at odd hours. “It’s one reason our marriage works so well,” he said.

The office is where the couple spend the majority of their time. Mr. Walters and his wife have adjacent desks facing an 85-inch television mounted above a built-in Brazilian-walnut-driftwood wall panel. It’s also home to what Mr. Walters calls his mascot—a sculpture of a football referee. “It reminds me that the most important thing in our life is to have fun and keep things light,” he said.

Mr. Walters was born in the tiny town of Munfordville, Ky., and raised in a home with no indoor plumbing. His father and uncle were poker players, which he said helped fuel his passion for gambling, which is he calls “a way of life.” In the early 1980s Mr. Walters moved to Las Vegas to play poker full-time; he said he eventually tired of the game and moved on to sports betting.

Mr. Walters, now one of the world’s highest-earning sports bettors, often places wagers with Las Vegas casinos through anonymous partnerships. To make decisions, he uses research from various analysts he contracts, from mathematicians to experts in sports minutiae. “Betting on a ball game is identical to betting on Wall Street,” said Mr. Walters.

His career rise hasn’t come without some controversy. Mr. Walters has been indicted four times over the years on money laundering and illegal bookmaking charges. Each time, he has either been acquitted or had the charges dismissed without a trial.

He currently owns eight car dealerships and a Las Vegas-based recreational property company that owns and operates golf courses, shopping centers and commercial properties. (Gambling now accounts for about 20% of his total earnings, he said.)

In 2002, Mr. Walters and his wife purchased two adjacent beachfront lots with a private entrance to Terramar Beach for about $5.8 million. The home’s location, an eight-minute drive from a private airport, was a big selling point, as Mr. Walters can hop on his Gulfstream 200 jet and make it here in 75 minutes, door-to-door, from his Las Vegas office.

Mr. Walters said the couple then spent three years and more than $25 million tearing down an existing house and rebuilding. Mrs. Walters, who worked with a local design firm and an architect, said her goal was for the house to “blend in with the landscape around it.” His wife, joked Mr. Walters, has “exceeded every budget we’ve set for her.”

Last week, the couple completed a new home in Cabo San Lucas, Mexico. They also own homes in Las Vegas, the Bahamas and two in Palm Desert, Calif. The seventh is under construction in Rancho Santa Fe, a short drive inland from Carlsbad.

Mr. Walters said making money off his houses isn’t his goal—he just likes living in them and his wife likes designing them. “It works for us,” he said. “And, honestly, every six or seven years I’m ready to move into a new house anyway.”

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