B
oston Real Estate Times celebrates leaders who transform communities, not just shape skylines. This year's Real Estate Development Leadership Award goes to Damien Chaviano, Co-President and Principal at Samuels & Associates. His vision has redefined Boston's urban fabric.
Chaviano's work is helping write the next chapter in a city steeped in history. From Pierce Boston to Lyrik Back Bay, his projects are destinations that blend iconic landmarks with community-driven design. At the Excellence Awards Gala on September 11, 2025, Chaviano will be honored for his leadership style and commitment to bridging business and community.
A Developer Rooted in Community
Chaviano's story begins far from Boston, in a quiet suburb northwest of Chicago. His father, who left Cuba alone at 13, built a life through grit and determination. Chaviano's mother's constant relocations instilled a dynamic worldview that he brings to every project today.
These values carried him from launching a high school car detailing business to enrolling in the prestigious MSRED program at MIT. His career has spanned all facets of the industry, including capital sourcing, underwriting, and design. Returning to Samuels & Associates marked a pivotal moment, 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 Chaviano's leadership, the firm remains focused on transforming neighborhoods into vibrant, inclusive places where people live, work, and connect.
Pierce Boston is one standout example, seamlessly integrating 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."
Leading by Example
Chaviano's resume is impressive, but it's his willingness to be hands-on and relentless pursuit of impact that sets him apart. Take the Trio project in Newton: a 160-unit apartment development that faced intense community resistance. After 22 hearings, Chaviano finally received approval for a project he believes has become a hallmark for the community.
That balance between complex projects and improving lives through development is what defines Chaviano's legacy. His leadership style bridges business and community, ambition and authenticity.
Q&A with Chaviano
Boston Real Estate Times: What sparked your interest in real estate?
Damien Chaviano: I was driven early, starting my own car detailing business in high school. Then, The Apprentice aired, and I became obsessed. I relentlessly pursued an internship with a Boston-based developer and landed a role on a residential golf course development.
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. I took every task seriously and invested in financial skills through night classes and grad school at MIT.
BRET: Was there a mentor or role model who shaped your path?
DC: Several mentors have pushed me to grow and never stop believing in myself. One business partner challenged me to take the leap and be the developer I always wanted to be.
BRET: What was the most impactful or rewarding moment of your career?
DC: The Trio project in Newton was a turning point. It took 22 hearings, but we got it done. That project brought needed housing and commercial vibrancy, and now my family shops and dines there. My kids are proud of it.
Damien Chaviano's journey from intern to award-winning leader is about betting on vision, doing the work, and building community every step of the way. His impact will be felt for decades to come.
To purchase tickets for the Boston Real Estate Times Excellence Awards Gala on September 11, 2025, click here.
