Dominic Paolillo

Dominic Paolillo brings over three decades of experience, passion, and precision to Truman & Company in Key West. With more than $400 million in real estate sales, Dominic is a trusted guide for buyers and sellers navigating one of life’s most personal and important journeys. From luxury condominiums to historic townhomes, new developments to co-ops, Dominic’s expertise is both broad and deeply nuanced.

Known for his impeccable attention to detail and his background in hospitality, Dominic offers an elevated level of service rooted in over 18 years in the service industry. He’s especially skilled at managing complex transactions, streamlining the process with grace, knowledge, and timeliness and calm under pressure.

Originally from Branford, Connecticut, Dominic launched his real estate career after a successful chapter in musical theatre, performing in more than 30 productions across the country. Dominic is still deeply immersed in the arts, performing at the beloved Waterfront Playhouse, The Fringe Theater and The Red Barn Theater in Key West. A proud resident of Midtown West, Key West, Dominic shares his home with his partner and their two rescue dogs, Brixen and Shiloh.

Dominic is also an active member of the Key West Business Guild, where he supports LGBTQ+ business initiatives and fosters community growth. His philanthropic efforts span a wide range of causes, including the Animal Medical Center, The Central Park Conservancy, Lambda Legal, and The Key West Garden Club.

His achievements in the field have been recognized in Bloomberg TV, The Real Deal, Christie’s International Real Estate, and more. He was ranked #12 company-wide at his previous firm and represented the purchaser of a $40 million sale at 2 East 70th Street.

Whether you’re buying, selling, or simply exploring the market, Dominic is your go-to expert in Key West. With a background that blends creativity, business acumen, and heartfelt service, he is ready to help you unlock the next chapter of your real estate story.