Laura Barry and Jason Barry of Rancho Santa Fe’s Barry Estates Get Personal

San Diego is home to an impressive roster of the super successful, including tech moguls, pro sports superstars, entrepreneurs, entertainers, financial wizards, and more — some so private, many of us may not even be aware they live among us; others are well-known neighbors. Oddly, a segment often overlooked when we think of the movers and shakers in San Diego are the local real estate professionals who not only connect some of our most notable residents with their homes, but who are impressively successful in their own right. Among them are two of the most accomplished agents in San Diego, Laura Barry and Jason Barry. 

The sister and brother who are consistently vying for No. 1 honors in San Diego real estate production are not, however, a team. They’re each other’s hottest competition, though their individual operations both fall under one umbrella, Barry Estates. With offices on opposite sides of Paseo Delicias in the heart of the village of Rancho Santa Fe, they know their toughest opponent better than anyone else, but they also know that they’re each other’s greatest ally. “We’re stronger apart,” says Laura. Working together, Jason jokes, would be “like having Tom Brady and Peyton Manning on the same team. NFL football is better with them both on the field competing.” Laura has one business partner, Jim Graves, who comes from a strong financial background, while Jason has two, Ryan McGovern and Kendra Gibilisco, who each bring a wealth of knowledge, massive rolodexes, and commitment to the team.

If you ask Jason and Laura, one of the keys to their success is a work ethic established early on by their parents, Catherine and Daniel Barry. “My parents were teachers, and they moved [to Rancho Santa Fe] when we were in grade school primarily because they wanted to give their kids a better chance through education,” remembers Jason, who says they were drawn to the area in 1977 for Rancho Santa Fe’s award-winning school, now R. Roger Rowe School. With a Mensa-level IQ, Catherine eventually tried her hand at real estate. “In the first month, my mom made her teaching salary,” he remembers. “And in the second month, she made his.”  The two then launched Barry Estates. 

Laura credits her father for their tenacity. “Our father was from Dublin, Ireland, so that immigrant mentality [was] really highlighted as we were growing up, how fortunate we are to live in this country. There are things you can do in this country that you can’t do in other countries. So, the way we look at things is kind of through the eyes of our father.”

Respect for their family’s history is a driver in both Laura’s and Jason’s careers. “It’s a legacy,” says Laura. And though neither immediately leapt into the family trade initially, it’s astounding that in 2021 and 2022, Barry Estates sold $1 billion in real estate each year. Their brother, Sean Barry, an attorney who originally joined the team in 2018 as a broker, founded his own Luxury Coast Group of Barry Estates with a small team in Del Mar in 2022. And now, a next generation of Barrys is set to enter the real estate world, as Jason shares that his son Connor recently passed his real estate license exam. 

Having one another to push them to the pinnacle of success has also proven critical in harder times. In 2019, they lost their mother and their father, and Jason’s wife succumbed to a battle with cancer. “Laura was unbelievably supportive and an incredible sister to me at that time, and it did bring us together, there’s no doubt,” Jason says. He leaned into work as a way to push through as well as to honor them. “For me, work was therapeutic,” he says. “And my kids and I, we had a choice. How are we going to react to this devastation? We are going to do the best that we can in everything we do, and that’s it. So that’s what we did.”

Which is not to say they’re all work and no play. “I think it’s really important to recharge and disconnect,” says Laura, a Covenant resident. “I tell my clients, ‘Life is short. You’re not here forever. Don’t be the richest man in the graveyard.’” Even so, she admits that her phone is never far from her (she closed a $15 million deal remotely from Positano, Italy last year). 

Still, it’s not hard for them to find motivation to return to the office after jetting off for a respite. “We love what we do, and look where we live!” exclaims Jason, who lives in Fairbanks Ranch and is now happily remarried. “I don’t think there’s a better lifestyle anywhere in the world.”

ABOUT THE HOME  This brand new 7-bed, 11-bath, 10,350-square-foot custom estate on Ladys Secret Drive in the prestigious gated community of Del Rayo Estates boasts unobstructed views over the San Dieguito River Valley to the coast beyond. The home offers the epitome of luxury living and is currently listed with Laura Barry of Barry Estates