Maine Real Estate & Waterfront Business Part 2: Chris DiMillo on Family, Real Estate, and the Portland Waterfront

Send us Fan MailIn this second half of my conversation with Chris DiMillo, owner of DiMillo’s Yacht Sales, we dive deeper into how he expanded his family’s Maine waterfront legacy — growing the yacht brokerage business beyond Portland to Long Island, New York and the eastern shore of Maryland — all while maintaining a culture grounded in hospitality, service, and relationships.Chris shares his insights on:🌊 Scaling with purpose: How a single boat sale led to multi-state expansion and a thriving 70-person company.⚓ Company culture: The “hospitality DNA” inherited from his father that drives both employee loyalty and exceptional client service.💡 Adaptability and resilience: How the COVID-19 pandemic reshaped the boating industry — from shutdowns to record demand.🧭 Vision for Portland’s waterfront: Chris’s candid take on what “highest and best use” should mean for the city’s working waterfront and development future.💬 Personal reflections: On family legacy, mentoring the next generation, and what his father would think of the business today.Chris’s story is a quintessential example of Maine entrepreneurship — rooted in family, built on service, and always looking toward the horizon.Links Mentioned:🛥️ DiMillo’s Yacht Sales: https://www.dimillosyachtsales.com⚓ DiMillo’s Marina: https://www.dimillosmarina.com🍽️ DiMillo’s on the Water (Restaurant): https://www.dimillos.comElegant 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.