Every gated community in Rancho Santa Fe has a name. Few have a story quite like this one.

Tucked behind the gates of Del Rayo Estates — one of the Ranch’s smallest and most private enclaves, just 23 estate lots in total — sits a cul-de-sac named for a champion. Not a person. A racehorse. And not just any racehorse: Lady’s Secret, the gray daughter of Secretariat who became, for one unforgettable season, the fastest thing on four legs in American sport.

This week, the Jason Barry Team is bringing a rare offering to market at the heart of that story: 5910 Ladys Secret Ct, listed at $8,995,000.

The Man Behind Del Rayo Estates

Long before Del Rayo Estates existed, Eugene “Gene” Klein was building an unlikely American success story. Born in the Bronx, Klein flew bombers in World War II before making his way to California, where he built a fortune first in the used-car business, then as chairman of National General Corporation, a Los Angeles-based entertainment and insurance conglomerate. Along the way, he co-founded the Seattle SuperSonics of the NBA and, in 1966, led the investor group that purchased the San Diego Chargers for a then-record $10 million.

Klein owned the Chargers for 18 years, presiding over the “Air Coryell” era of the late 1970s and early 1980s — the high-scoring offense built around future Hall of Famers Dan Fouts, Kellen Winslow, and Charlie Joiner that made the Chargers must-watch football and delivered three straight AFC West titles. He sold the team to Alex Spanos in 1984.

It was around that same period that Klein’s attention turned to Rancho Santa Fe — and to horses.

A Racing Stable, Not Just a Real Estate Deal

In 1982, Klein established Del Rayo Racing Stables, a 237-acre breeding, training, and boarding operation in Rancho Santa Fe, and hired Hall of Fame trainer D. Wayne Lukas to run it. What followed was one of the more remarkable runs in modern American racing. Lady’s Secret carried Klein’s colors to the 1986 Horse of the Year title, but she wasn’t alone: Klein’s stable also produced Winning Colors, just the third filly in history to win the Kentucky Derby (1988), and Open Mind, back-to-back Eclipse Award winner as champion 2-year-old filly in 1988 and champion 3-year-old filly in 1989. His horses also captured three straight Breeders’ Cup Juvenile titles in the mid-to-late 1980s.

It was this same stable operation, sitting on prime Rancho Santa Fe acreage, that gave Klein the foundation to launch a real estate venture in the mid-1980s: two adjoining residential communities he called Del Rayo Estates and Del Rayo Downs. When it came time to name the streets of his new luxury enclave, Klein didn’t look far for inspiration — he named them after the champions who had made his name in racing.

A Street Named for a Champion

Lady’s Secret earned her tribute the hard way. In 1986, the small, unassuming gray mare did something almost no filly in racing history had done: she beat the boys. Four times that season, Lukas sent her up against the best male horses in the country — and in the Whitney Handicap at Saratoga, she became the first filly or mare in nearly forty years to win it outright. By year’s end, she’d earned the nickname “The Iron Lady,” swept the Breeders’ Cup Distaff, and claimed the sport’s most prestigious honor: Horse of the Year. She was inducted into the National Museum of Racing and Hall of Fame in 1992.

Alydar Corte, the community’s other street, carries its own racing pedigree — named for Calumet Farm’s Alydar, Affirmed’s legendary rival in the 1978 Triple Crown, famous for finishing a heartbreakingly close second in all three Triple Crown races that year.

Klein’s connection to Rancho Santa Fe outlasted his racing career. In poor health, he retired from the sport in 1989 and sold his stable of 146 horses just months before his death in 1990. In 1995, his stables were sold to Sidney and Jenny Craig — of Jenny Craig weight-loss fame — a footnote that speaks to just how coveted this stretch of Rancho Santa Fe has remained across ownership changes. By 2005, Forbes ranked the surrounding 92067 ZIP code as the second most expensive real estate market in the entire United States.

It’s the kind of backstory that turns a street sign into a piece of history — and it’s part of what makes Del Rayo Estates feel less like a subdivision and more like a private tribute, hidden in plain sight.

The Next Chapter

Set on 2.23 elevated acres within that same storied cul-de-sac, 5910 Ladys Secret Ct is entering a new chapter of its own. The lot currently holds a 2-bedroom, 1-bathroom guest house and a north/south facing tennis court — the bones of a resort-style estate ready for its next life.

What sets this offering apart today is what comes with it: HOA-approved plans for a new 12,000+ square foot main residence, designed by respected San Diego architect John Jensen, whose custom residential work has shaped some of the region’s most recognizable coastal and Rancho Santa Fe estates since 1988. For a buyer drawn to Del Rayo Estates but unwilling to spend years navigating entitlements, the path to a legacy home here is already paved.

Life Behind the Gates

Del Rayo Estates sits along San Dieguito Road, a short walk from the Forbes five-star Rancho Valencia Resort & Spa, just south of Del Rayo Downs and north of the Del Mar Country Club. It’s a rare combination in Rancho Santa Fe: resort-level amenities within walking distance, wrapped in the privacy of a community with only 23 homes to its name. The coast, the I-5, and the boutiques and restaurants of Rancho Santa Fe Village are all just minutes away.

Recent Sales in Del Rayo Estates

The strength of Del Rayo Estates shows in its recent numbers. In July 2025, 5968 Ladys Secret Ct — a brand-new, 12,000-square-foot custom estate on the same street, listed by Laura Barry of Barry Estates — sold for $18,000,000, setting a new price-per-square-foot benchmark for the community. On Alydar Corte, 6883 Alydar Corte, a 12,756-square-foot European-style estate, closed for $10,536,831 in October 2024.

Together, those sales tell a clear story: buyers are paying a premium for newly built, architecturally significant homes within Del Rayo Estates’ gates — exactly the opportunity a fresh, HOA-approved build at 5910 Ladys Secret Ct represents.

Ready to see it for yourself? Contact the Jason Barry Team to schedule a private tour.