Maine Real Estate & Waterfront Business: Chris DiMillo on Family, Real Estate, and the Portland Waterfront

Send us Fan MailIn this episode of Elegant Maine Living, I sit down with my friend and client, Chris DiMillo, whose family name is synonymous with Portland’s waterfront. The word of the day is DiMillo—because that single name tells a story of hard work, family, entrepreneurship, and Maine grit.Chris shares his father’s remarkable journey—growing up on Munjoy Hill, leaving school at age 12 to help support his family, and ultimately building an empire that would shape the heart of Portland. From running a grocery store to creating one of Maine’s most iconic restaurants, his father’s story embodies the spirit of possibility that defines the Maine lifestyle.We also talk about Chris’s own path—leaving Maine for California, building a career in medical sales, and then returning home to take over the marina and launch DiMillo’s Yacht Sales, now a thriving business with multiple East Coast locations. Chris shares what it’s like to lead a team of 70, grow a family business with intention, and continue his father’s legacy on Portland’s working waterfront through DiMillo’s Marina.Our conversation also turns to real estate—how his father’s early investments helped transform Commercial Street and how zoning and development continue to shape Maine real estate today. Chris offers thoughtful insight into the balance between preserving Portland’s working waterfront and allowing for growth that keeps the city vibrant and sustainable.If you’re in Portland, make time to experience the DiMillo family’s legacy firsthand at DiMillo’s on the Water—a floating restaurant that has become a Maine landmark for locals and visitors alike.This episode is a celebration of family, entrepreneurship, and the enduring beauty of living and working in Maine—where hard work, creativity, and community come together to define success across generations.Links MentionedDiMillo’s on the Water (Restaurant): https://www.dimillos.com/restaurant/DiMillo’s Marina: https://www.dimillosmarina.com/DiMillo’s Yacht Sales: https://www.dimillosyachtsales.com/Elegant Maine Living explores Maine’s homes, communities, and people—through the lens of lifestyle, values, and thoughtful living. I host conversations with leaders, creators, and advisors who help illuminate what it truly means to live well in Maine.Connect with Elise🌐 Website & Listings: EliseKiely.com 📸 Follow Elise on Social Media:Instagram: @elisekielyrealestateFacebook: Elise Kiely Real Estate LinkedIn: Elise Kiely Have Questions or Topic Suggestions, e-mail Elise at [email protected], share with a friend, and join Elise every other week to discover what makes Maine not just beautiful—but beautifully lived.Please remember this podcast is for entertainment and educational purposes only and does not create an attorney client or real estate advisor client relationship.  Please reach out to me directly if I can assist you in your real estate journey.