For Larry Brennan, a lifelong fascination with real estate began at an age when most kids were thinking about anything but houses.

When Larry was 12, his mother was considering moving the family into a larger home. She took him along to open houses, and, somewhat unexpectedly, he loved it. The family never moved, but Larry’s curiosity about homes and the real estate market stayed with him.

“I was always interested in watching the real estate market from that point on,” he recalls.

That early interest would eventually become a second career, but first Larry took a more traditional route. Raised in North Central New Jersey in what he describes as a loving home, he attended Indiana University in Bloomington, where he earned a bachelor’s degree in economics. After college, he returned to New Jersey and began working in finance and technology.

His career took him from banking into the brokerage industry, where he worked in technology and eventually became a Senior Technology Architect and Project Manager. Along the way, he earned a master’s degree in information systems while working full time, married his college sweetheart, and became a father to three boys.

Then came a move that changed the direction of his life.

As his children grew older, Larry and his family began looking for a community with better schools and lower property taxes. They ultimately settled on St. Michaels, Maryland, in 2011.

Before the move, Larry had already gotten his first taste of being a real estate entrepreneur. Rather than hiring an agent to sell the family home, he listed it himself.

“I sold it within a week for just a few thousand under our asking price!” Larry says.

After moving to St. Michaels, he continued working remotely for his New Jersey employer for about six months. Then, in 2012, he made the leap into real estate.

Starting over was not easy. Building a business from scratch took time, but Larry gradually developed a pipeline of clients, closed several transactions, and discovered that the career he had been curious about since childhood was exactly where he wanted to be.

“I loved the work,” he says. “It was slow going at first, starting a new business from scratch, but after the first year I had built up a pipeline of clients, closed a few deals and I was hooked.”

Today, Larry works as an individual agent with TTR Sotheby’s International Realty. In 2025, he earned the brokerage’s over-$10-million sales achievement award.

Yet success, for Larry, is not simply about increasing the number of transactions. His philosophy is deliberately personal.

“I’m not trying to do 50 transactions a year,” he says. “I want to give clients the attention they deserve. I care much more about my clients making the right decision then making a sale.”

That philosophy has translated into relationships that extend well beyond the closing table. More than half of Larry’s business now comes from past clients referring friends and family.

“The most fulfilling thing for me is getting referrals from past clients,” he says. “I have lots of clients that I now call friends.”

Larry credits his previous career with teaching him how to communicate clearly, respond quickly, and remain level-headed when problems arise. In the brokerage industry, he learned that a mistake could quickly become a multimillion-dollar problem, making communication and thoroughness essential.

Those lessons remain central to how he works with clients today.

“I pride myself in keeping a level head and ensuring my clients are well informed so they can make the right decisions.”

Away from real estate, Larry is enjoying a different kind of busy life. His three sons are now adults, and he takes pride in the men they have become. He and his wife enjoy traveling, going to concerts, and spending time around St. Michaels.

Their 10-month-old Goldendoodle, Ziggy Stardust, is also part of the picture.

The couple married in Las Vegas on St. Patrick’s Day in 2025. It was a second marriage for both, and Larry says they initially intended to “keep it casual.” Instead, they found themselves falling deeper in love.

Today, Larry is grateful for the life they have built.

“I truly believe the old saying, do what you love and you'll never work a day in your life,” he says. “I love meeting new people to either help them buy a home or sell their home.”

For Larry, the goal is simple: keep helping people, keep making new friends, and keep enjoying the life he has created along the way.

“Be yourself, be honest,” he advises. “Treat every client like they are a close friend or family.”