When former MLB first baseman Dorian “Doe” Boyland decided to list his incredible Hawaiian retreat, he wasn’t just putting another luxury home on the market. He was offering a piece of paradise — for people who can afford it, of course. According to a recent feature on Robb Report, this seven-bedroom estate in Maui’s Kapalua Resort has hit the market for a staggering $26.9 million.
The property shows how one player transformed his brief MLB career into lasting wealth and lifestyle dreams. I mean, I’m taking notes here (minus the brief MLB career part, but still).
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A Resort-Style Paradise That Redefines Luxury Living
What sets Boyland’s Hawaiian home apart isn’t just its amazing location between a jungle ravine and the 17th tee of the Kapalua Plantation Course. Tori Latham of the Robb Report noted that this masterpiece features amenities that’d make even a seasoned luxury real estate enthusiast do a double-take.
The crown jewel is a massive 45,000-gallon negative-edge infinity pool complemented by a 1,200-gallon spa, complete with a slide and swim-up sunken bar that turns any gathering into an unforgettable experience. Floor-to-ceiling windows and motorized sliding doors create easy indoor-outdoor living (which, I’d imagine you’d like to have the option to do in Hawaii), while outdoor showers and tubs provide the perfect post-swim rinse with unreal ocean views.
But here’s where it gets interesting for sports fans: Boyland didn’t just settle for proximity to a world-class golf course. He added two tee boxes, two putting greens, and four sand bunkers right on the property. Add in a game room, exercise facility, and theater with authentic movie-theater seating, and you’ve got a setup that rivals any professional training facility.
Boyland Had a Short But Well-Timed MLB Career
The first baseman spent parts of three seasons with the Pittsburgh Pirates: 1978, 1979, and 1981. He didn’t get much playing time during his big-league tenure, though. Boyland appeared in 21 games and racked up just 20 plate appearances in the process. He slashed .105/.150/.105, collecting two hits overall.
Boyland didn’t rack up any postseason playing time, but he was part of the Pittsburgh Pirates’ legendary 1979 World Series championship team. Pittsburgh was nicknamed “We Are Family” in 1979 after the Sister Sledge hit that became their theme song. They overcame a 3-1 deficit to defeat the Baltimore Orioles in one of the more dramatic World Series comebacks ever.
Although he doesn’t get credit for a World Series title on his Baseball-Reference page, Boyland has a ring to show for his efforts. “I was very fortunate to be involved with the 1979 Pittsburgh Pirates,” he said during a 2011 promotional video (via SABR). “I’ve got the [World Series] ring on right now. That was a dream in itself. I still get asked today, ‘How was it?’”
The Business Empire That Built This Paradise
Boyland’s transition from baseball to business mogul is one of the more impressive athlete-to-entrepreneur transformations you’ll see. As Latham noted, Boyland pivoted into the auto industry after his MLB career was officially over, where he built and operated a series of car dealerships across the United States.
Black Enterprise magazine also recognized him as one of the top auto dealers in the country. This wasn’t just about owning a single dealership. Boyland created a multi-location empire that generated the kind of wealth that makes owning a $26.9 million Hawaiian estate a reality instead of a pipedream.
What This Sale Reveals About Athletic Success and Legacy
This estate sale is intriguing because it shows the evolution of athlete wealth management and lifestyle choices. Unlike many sports figures who invest heavily in traditional real estate markets (along with making a lot of money while playing their respective sport), Boyland created a personal paradise that served as a family retreat, entertainment venue, and investment property.
The inclusion of over $1 million in custom furnishings (with some exceptions) and high-end appliances shows how much thought went into creating not just a house, but a complete lifestyle experience. Premium finishes, including Acadia wood flooring, Supreme Blue Moon marble, and Busby Greystone cabinets, showcase his attention to detail that mirrors the precision required for both athletic and business success.
The fact that this property can accommodate hundreds of guests while maintaining intimate family spaces reveals Boyland’s understanding of how to leverage luxury real estate for both personal and business purposes. It’s a masterclass in creating value that extends beyond simple square footage or settling in the perfect location. It’ll be interesting to see who eventually takes it off his hands.
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