By: William Jones

Michael Flavin has spent his entire life in Quincy, Massachusetts. He went to Quincy schools, attended the University of Massachusetts at Dartmouth, and returned home to build a career in real estate. This year marks his 30th year in the business. The company he runs, Flavin & Flavin, just celebrated its 100th anniversary.

That kind of timeline is rare. Most agents move around. They chase markets or follow opportunities elsewhere. Michael stayed. He knows the streets, the schools, the families who have been here for generations.

More Than a Real Estate Agent

When a client asks where to get a good haircut for their kids, Michael has an answer. When they want to know where to eat, he can point them in the right direction. He considers himself a full resource for anyone looking to settle in the area.

“I live my entire life in the area I sell real estate,” Michael said. “I offer not only real estate service in Quincy, but I’m a full resource for my clients. I know where the best places to eat are, you want the best steak in Quincy, go to Alba Restaurant, where to get your dry cleaning done, and where the better barber shops are for the kids.”

That knowledge is not something you can fake. It comes from walking the same sidewalks for decades, watching businesses open and close, seeing neighborhoods change over time. Interesting point he makes, Michael will not take clients outside his area. If someone needs an agent in a different town, he refers them to someone who knows that town the way he knows Quincy.

“Agents say with the data online, you can serve all areas,” he explained. “Maybe, but I believe the best agents are the ones who sell in the areas they have lived in.”

His investment in Quincy goes beyond his work. Along with his brother Tim, Michael owns over 100 residential units in the city. He is financially tied to the community, not just professionally connected to it.

Football and Fatherhood

Before real estate, football shaped a significant part of his life. Michael had a successful career in high school and college, enough to be inducted into the Football Hall of Fame. He later returned to both schools as a coach. Today, he serves as head football coach for Quincy Youth Football, where he coaches his son, Jonathan. In 2015, he was named Massachusetts Youth Football Coach of the Year. This past year, Michael’s team, Quincy United, won the Massachusetts Youth Football State Championship. Mike’s son Jonathan was the game’s most valuable player. Throughout this interview, Mike lit up whenever he mentioned Jonathan. 

“My favorite job is being a father,” he said.  I’m blessed to have the most amazing son and three well-accomplished stepchildren, whom I love very much. “ Michael played an extremely important role in raising his stepchildren. “ Being there for them has been incredibly rewarding. Seeing them grow and succeed reinforces the importance of guidance and support in their lives, and I’m grateful to be a part of their journey”.  When it comes to Jonathan, they are simply inseparable. 

Building Client Portfolios

Coaching youth sports and running a business both require patience and the ability to teach. Michael brings both to his work with clients, particularly those looking to build a real estate portfolio. He takes pride in helping people start small, maybe with a three-unit building, and then guiding them as they grow into larger investments over time.

“Nothing excites me more than when I sell someone their first piece of property, then years later they have multiple buildings,” Michael said. “It excites me when my clients make money in real estate through my guidance and advice.”

Recognition and Giving Back

According to MLS data, Michael was the City of Quincy’s top producer in 2009, 2010, and from 2013 to 2019. In 2020, Broker Agent Advisor named him among the top 500 agents in the United States, awarding him the Seven Star Award for excellence in performance and community leadership. Flavin & Flavin has maintained an A-plus rating from the Boston Better Business Bureau for 20 consecutive years, from 2005 to 2025.

More recently, Michael received an honorable mention as Norfolk County’s Comeback Businessman of the Year in 2025. That same year, he earned recognition through the Five Star Award from Pine Street Inn homeless shelter for volunteering over 40 hours a month. He spends that time speaking with shelter residents, helping them apply for jobs, build or repair credit, and understand the importance of sobriety in building success in business and parenting.

Learning From Mistakes

When asked about his approach to life, Michael speaks openly about learning from his mistakes. He views every failure as a chance to figure out what does not work, and that mindset has helped him build resilience over time.

“My biggest strength in life is that I learn from my mistakes,” he said. “Facing the consequences of my errors built my emotional and mental strength, equipping myself to handle challenges more effectively and teach others the same.”

He believes that owning his past failures has also helped him connect with clients and employees. Sharing what went wrong and being accountable for it builds trust.” I let many people down because of my mistakes, especially my loved ones. It was difficult for me to ask for forgiveness for the mistakes I made. Acknowledging my wrongdoings required a lot of courage and humility. I knew my actions had affected others, and coming to terms with that was not easy. Letting down people you love is an awful feeling that stays with you 24/7. However, I realized that seeking forgiveness was a vital step toward healing. It was a humbling experience that taught me the importance of accountability and the value of making amends, “ he says. “  Forgiving myself is something I continue to struggle with.” 

“Recognizing my own mistakes allows me to have greater empathy toward others,” Michael explained. “Sharing my experiences of past failures and being accountable for them has built trust and credibility, making it easier to connect with others and gain their trust.”

That kind of honesty is not common in sales. But it fits with who Michael is. He is someone who stayed in one place, built slowly, and put relationships ahead of volume. He went through some hard times but came back better and stronger. After 30 years and a century of family history in the business, he keeps doing what he knows. And what he knows is Quincy.

Disclaimer: Any metrics, awards, or timelines mentioned may change over time and are subject to verification. Readers should interpret the content with the understanding that certain details could vary based on the most recent data available.