Michael Cupolo

A native New Yorker, Michael Cupolo’s passion for real estate began at an early age. After attending LIU and graduating from Florida Atlantic University, Mike knew that a career in real estate was the next natural step. Upon returning to New York, he joined The Heyman-Cupolo Team at Sotheby’s International Realty in 2015. Through this dynamic and high-performing team, Mike was quickly immersed in some of the most luxurious real estate in the world—and he hasn’t looked back since.

Mike has closed a wide range of transactions across Brooklyn and Manhattan, with a specialized focus in neighborhoods such as Dumbo, Brooklyn Heights, Cobble Hill, Boerum Hill, Downtown Manhattan, and the Upper West Side. His expertise spans resale condos and co-ops, townhomes, new development sales, and high-end rentals. Him and the team consistently sets sales records, are frequently tapped by developers to lead new projects, and remain as trusted resources for repeat and referral clients who value their experience, discretion, and results-driven approach.

Mike’s market knowledge, strong negotiating skills, and ability to anticipate the needs of his clients make him a trusted advisor in all stages of the process.

Highly competitive, deeply committed, and consistently reliable, Mike is known for going to great lengths to ensure his clients’ goals are met with precision and care. He takes the time to understand every client’s unique situation, offering thoughtful guidance while making the process clear, enjoyable, and as stress-free as possible. Communication, trust, and adaptability are at the core of his approach. Mike makes himself available seven days a week and prides himself on being a calm, honest, and steady presence throughout every transaction.

Outside of real estate, Mike enjoys playing hockey and spending time with his wife, Jessica, their son, Mikey, and their rescue dog, Kyla. He had an accomplished collegiate hockey career—serving as team captain and later as a coach. In that role, he worked alongside several NHL athletes at both the collegiate and prep school level. Coaching taught Mike invaluable lessons in leadership, accountability, and teamwork—all of which directly translate to how he operates within The Heyman-Cupolo Team and in service to his clients.

Mike is also committed to giving back. He is a proud sponsor of the ASPCA and actively supports The Garden of Dreams Foundation, a nonprofit dedicated to positively impacting the lives of children facing illness, homelessness, or extreme poverty. For Mike, success isn’t just about closing deals—it’s about making meaningful connections and creating a positive impact both professionally and personally.