Fifty Stones Capital Group Closes Strategic High-LTV Loan for Iconic $29M Kailua Beachfront Estate.

Kailua, Hawaii — October 16, 2024 - On a private stretch of one of the world’s most picturesque beaches, tucked beneath the swaying palms and wrapped in ocean mist, sits a gated estate so opulent, it might be mistaken for a film set. With over 14,000 sq. ft. of masterfully crafted living space, this nine-bedroom oceanfront retreat in Kailua is less of a home and more of a resort in disguise, and as of this October, it became the centerpiece of a deal that most lenders wouldn’t dare touch. That’s what made it the perfect challenge for Fifty Stones Capital Group. When a seasoned borrower approached with a $29 million second-position funding request (with a first-position fallback of $14M), the initial reaction from traditional capital sources was predictable: too complex, too risky, too much shoreline. But for Fifty Stones, this wasn’t a red flag, it was a green light.

Set on nearly one acre of private beachfront land, this architectural marvel isn’t just a real estate trophy, it’s an income-producing asset with luxury vacation rental potential, media and event hosting capabilities, and long-term equity appreciation tied to the scarce supply of true oceanfront property in Kailua. But the challenge wasn’t the real estate, it was the capital structure.

The sponsor, an experienced luxury investor, was seeking a high-leverage, second-position loan of $29 million to unlock liquidity without disturbing existing favorable debt. If a second-position was off the table, he was prepared to pivot to a $14 million first-position bridge, but only if a partner could meet the deal’s unique timing and underwriting complexity. That’s when the sponsor’s advisory team turned to Fifty Stones Capital Group, known in industry circles for doing what most lenders can’t, or won’t.

“This wasn’t just about funding a property, it was about backing a vision,” said Mark Shea, the CEO of Fifty Stones Capital Group. “You’re looking at one of the most exclusive beachfront properties in the U.S., with institutional-grade upside, in the hands of a highly capable sponsor. It needed precision underwriting, not a cookie-cutter playbook.” Fifty Stones conducted rapid diligence, securing high-level appraisals, leaseback potential analysis, and exit strategies within days. Their risk analysts even mapped potential zoning shifts, tourism flow trends, and weather mitigation studies to fully understand the collateral’s resilience and revenue horizon.

"Most lenders see sand and saltwater as a threat," said the firm’s Senior Partner. "We see scarcity and sophistication."

While the size and glamour of the deal attracted attention, it was the layers of complexity that made it a true test of lending expertise. Existing liens, title restrictions, coastal ordinances, and valuation methodology made it clear, this wasn’t a deal for the faint-hearted. But for Fifty Stones Capital Group, it was a perfect storm, and an opportunity to showcase the firm’s technical mastery, deep capital flexibility, and client-first mindset.

“This was one of those deals where you either know what you’re doing, or you stay out of the way,” said the Managing Director. “We didn’t just close it. We engineered it.”

About Fifty Stones Capital Group

Fifty Stones Capital Group is a premier private lending firm specializing in complex bridge loans, construction finance, and second-position funding nationwide. The firm has a reputation for moving quickly, thinking creatively, and backing high-stakes projects that demand more than just capital, they demand conviction.