BOSTON — Every year, the Boston Real Estate Times celebrates leaders who don’t just shape skylines, but transform communities. This year’s Real Estate Development Leadership Award goes to Damien Chaviano, Co-President and Principal at Samuels & Associates — a developer whose vision has been instrumental in redefining what Boston’s urban fabric can be.
In a city steeped in history, Chaviano’s work is helping write its next chapter. From iconic landmarks like Pierce Boston and Van Ness to the reimagining of the Landmark Center and Lyrik Back Bay, his projects aren’t just buildings — they’re destinations.
At the Excellence Awards Gala on September 11, 2025, at the Burlington Marriott Hotel, Chaviano will be honored not only for his professional achievements but for a leadership style that bridges business and community, ambition and authenticity.
To buy a ticket for the gala, please click here.
A Developer Rooted in Community
In a real estate industry often driven by transactions, Chaviano stands out for building more than just square footage. His story begins far from Boston — in a quiet suburb northwest of Chicago — but it’s one shaped by the values of hard work, family sacrifice, and education.
Chaviano’s father, who left Cuba alone at 13 following Castro’s rise to power, built a life in the U.S. through grit and determination. His mother’s constant relocations for her father’s sales job gave Chaviano a dynamic, adaptive worldview — something he brings to every project today.
These values carried him from launching a high school car detailing business to eventually enrolling in the prestigious MSRED program at MIT, where he formalized his understanding of the financial and architectural complexities of real estate development.
His career has spanned all facets of the industry: capital sourcing, underwriting, permitting, design, marketing, and investor relations. His return to Samuels & Associates in a leadership role in recent years marked a pivotal moment — and a homecoming — as he began shaping Boston’s skyline once again.
A Company on a Mission: Samuels & Associates
Samuels & Associates has long been at the forefront of community-centered development in Greater Boston. Under Damien’s leadership, the firm has remained laser-focused on transforming neighborhoods into vibrant, inclusive, and pedestrian-friendly places where people live, work, and connect.
One standout example is Lyrik Back Bay, a project that seamlessly integrates public space, sustainability, and infrastructure improvements with sweeping city views and civic energy. It’s a living example of what Chaviano calls “serving our communities and advancing their vision.”
With transformative projects throughout the Fenway, Allston, and beyond, Samuels & Associates continues to prioritize partnerships with local organizations, responsive design, and economic vitality — hallmarks of their approach that align perfectly with Damien’s personal values.
Leading by Example
Chaviano’s resume is impressive — managing over $1 billion in development projects at Mark Development, overseeing strategy and acquisitions at Samuels, and pioneering innovative approaches to mixed-use spaces. But what’s most striking is his willingness to be hands-on and his relentless pursuit of impact — even when the odds are against him.
Take the Trio project in Newton: a 160-unit apartment development that faced intense community resistance. “After 22 hearings,” Chaviano says, “we finally received approval for a project I believe has become a hallmark for the community.” The buildings brought new life to a formerly stagnant corner of town — along with housing, retail, and new civic energy. “Seeing how proud my kids are of the development has been incredibly rewarding,” he adds.
That balance — between the demands of complex, high-stakes projects and the deeply human experience of improving lives through development — is what defines Chaviano’s legacy.
Q&A with Chaviano
Boston Real Estate Times: How would you describe your formative years?
Damien Chaviano: I grew up in a bucolic suburb, 45 minutes northwest of Chicago, where my story was somewhat unique. After Fidel Castro came to power, my father left Cuba alone at the age of 13 to live with his uncle’s family outside of Elizabeth, New Jersey. He put himself through college and landed in Chicago for law school, where he met my mom. They had different personalities but shared two values that shaped me: hard work and a belief that you can’t put a price on the quality of education. I started my own car detailing business in high school — I was driven early.
BRET: What sparked your interest in your current field?
DC: My father saw success in careers like law, medicine, or finance — and I felt pressure to follow one of those paths. But I wasn’t interested. Then, six months before graduating college, The Apprentice aired — and I became obsessed. The winner would become the developer of Trump’s first high-rise condo-hotel in Chicago. That sparked something in me. I relentlessly pursued an internship with a Boston-based developer and landed a role on a residential golf course development in Ipswich. That changed my life.
BRET: What obstacles did you face and how did you overcome them?
DC: In 2004, the industry was dominated by people with construction or engineering backgrounds — or family names on the door. I had a liberal arts degree. I took every task seriously, no matter how small. But I also realized I lacked financial skills, so I took night classes and eventually enrolled full-time in grad school at MIT. Just two weeks after I graduated, Lehman Brothers collapsed. With development stalled, I shifted gears and looked for analyst roles at development companies. That bet — investing in capital markets expertise — proved to be the right move when the market returned.
BRET: Was there a mentor or role model who shaped your path?
DC: Several, and I mean that genuinely. My first boss in Ipswich told me he’d work for me someday — and treated me like a peer from the start. Later, at a career crossroads, another mentor pushed me to keep growing and never stopped believing in me. Most recently, a business partner appeared almost out of nowhere and challenged me to finally take the leap and be the developer I always wanted to be. His appetite for hard, unconventional work pushed me to take on the most difficult markets — and succeed.
BRET: What was the most impactful or rewarding moment of your career?
DC: It has to be the Trio project in Newton. I thought I was ready for community development outside of Boston, but I was unprepared for the intensity of the opposition. It took 22 hearings, but we got it done. That project not only brought needed housing but also real commercial vibrancy. And now? My family shops and dines there. My kids are proud of it. That makes it all worth it.
Damien Chaviano’s journey from a determined intern to an award-winning real estate leader isn’t just about personal success — it’s a story about betting on vision, doing the work, and building community every step of the way.
As Greater Boston continues to evolve, it’s clear that Damien’s impact — and that of Samuels & Associates — will be felt for decades to come.
Damien Chaviano will be honored at the Boston Real Estate Times Excellence Awards Gala on September 11, 2025, at the Burlington Marriott Hotel.
To purchase tickets, click here.
