After four years in an accounting career, David Cahill teamed up with his mother, who was a broker for more than 30 years. A Realtor with Century 21 Cityside, Cahill remembers his mother being in real estate since he was young, adding that his stepfather and sister also tried it. “I guess you could call real estate the family business,” he says, which is why he bought it when his mother retired in 2018.

Working mostly with first-time buyers and investors, Cahill has now been in real estate 19 years. And while he covers all of Boston (specializing in Dorchester), he enjoys helping people outside Beantown, too. “I have assisted buyers and sellers in 56 different cities and towns to date,” he explains. “I enjoy getting out of my comfort zone and learning about a new area when I have the opportunity.”

Focusing on customer service and attention to detail, Cahill knows the importance of making his clients feel valued by communicating even after the sale. “I’m very good about calling all my buyer clients on their home-purchase anniversaries,” he reveals. “It allows us to stay in touch, and it keeps me in mind for when they want to sell.” One of his biggest professional accomplishments was helping a family find a new home. After looking in many different areas, they finally found the right house. They offered $231,000 over asking price and managed to close the deal. 

Describing himself as down-to-earth, Cahill enjoys making his clients laugh, especially during showings. “They tend to have a better experience if they have fun during the process,” he insists. An avid Boston Red Sox fan and season ticket holder, Cahill enjoys mentoring with Big Brothers Big Sisters of America and serving as a high school youth group adviser at a local church.