Lessons from Local Leaders:

Jay Caputo

From Culinary Craft to Real Estate Artistry: A Conversation with Jay Caputo of Brushstroke Properties

Jay Caputo’s journey is anything but ordinary. From the adrenaline-fueled world of high-end kitchens to the fast-paced real estate market of the DMV, Jay has channeled his passion for crafting unforgettable experiences into a thriving career in real estate.

As the founder of Brushstroke Properties, Jay runs a boutique brokerage that approaches every transaction as a blank canvas—an opportunity to create a work of art tailored to each client. “We really try hard,” Jay shared. “We dive deep with our clients behind the scenes in order to understand their motivation.” That client-first mindset sets the tone for every interaction and decision his team makes.

Before launching his real estate career, Jay was a professional chef. He trained at the Culinary Institute of America and worked in major culinary hubs like San Francisco, Boston, and Philadelphia. Eventually, he opened his own restaurants in Rehoboth Beach, Delaware. But after becoming a father, Jay realized his demanding chef schedule was keeping him from what mattered most—his family. So he made a bold move, trading in his apron for a real estate license.

That transition wasn’t without its challenges. “They don’t give you a paycheck unless you sell houses,” he laughed, reflecting on the early days. But it didn’t take long for Jay to gain traction. He applied the same principles that had made him a successful chef—discipline, creativity, hospitality—to the world of real estate. “At first, I was a chef trying to sell homes,” Jay said. “Now, I’m someone helping people achieve their goals.”

Jay’s unique background inspired the ethos behind Brushstroke Properties. The brokerage operates in partnership with Side, allowing Jay and his team to focus on creating client-centric experiences while Side handles the backend brokerage operations. Jay describes his role as blending the art and science of real estate: art in the way his team crafts the client experience, and science in leveraging data to achieve the best results.

Jay’s passion for service also shines through in his community involvement. Whether it’s hosting junk removal events for local neighborhoods or cooking for his clients at an annual barbecue, he’s always looking for ways to give back. “If you have the opportunity to give, you should,” he said, especially when it sets an example for the next generation—his son included.

Through it all, Jay remains committed to unreasonable hospitality—going above and beyond in ways that clients will never forget. He shared a powerful story from his time as a chef when his restaurant comped an entire meal and filled up a couple’s gas tank simply to make their night unforgettable. “That’s the kind of experience I want to create for our clients,” Jay said. “I’m not chasing commissions—I’m chasing relationships.”

At Brushstroke Properties, that’s more than a motto. It’s the brushstroke that defines everything they do.

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