Our Story
Three Generations. One Mission
Our History
Since 1926, James W. Hennigan Insurance Agency has proudly served the Greater Boston area with honesty, reliability, and an unwavering commitment to personalized service. We’re not just in the neighborhood—we’re part of it.
Founded in Jamaica Plain and now proudly based in West Roxbury, our agency is built on three generations of family leadership and a deep understanding of what matters most to our clients. Today, under the guidance of James W. Hennigan III, we continue the tradition of offering thoughtful advice, competitive rates, and hands-on service to individuals, families, and small businesses across Boston.
From first-time homeowners in Hyde Park to contractors in Roslindale and families planning for the future in South Boston, we believe in building coverage—and relationships—that last.
Clear advice. Trusted support—backed by a team who sees you as more than just a policy.
At Hennigan Insurance, we don’t just write policies—we help you make confident decisions with clarity and care. We take the time to understand your needs, explain your options, and recommend coverage that fits your life—not someone else’s template.
Rooted in West Roxbury, with three generations of earned expertise, we guide our clients with professionalism, heart, and a neighborly touch.
And yes, that black Model A Ford with the red wheels out front? It’s more than a classic—it’s a symbol of our staying power and pride in serving the community for nearly 100 years.
Our Mission
To deliver high-quality service and competitive coverage—while serving the Greater Boston communities we know, love, and proudly call home.
What Makes Us Different
Locally owned and deeply community-involved.
Personalized Service
We take the time to get to know you—so we can recommend coverage that genuinely fits your needs, goals, and budget. We offer claims assistance, even after hours, when you need it most. Email us at jim@jimhennigan.com, and we’ll get right back to you.
Independent & Local
As a local, family-owned agency, we partner with respected carriers like MAPFRE, Quincy Mutual, and Norfolk & Dedham to compare options, offer competitive rates, and find the best fit for your needs.
Clear, Honest Guidance
We explain your coverage in plain language—no confusing terms, no pressure, just expert advice from a highly experienced team that cares about your peace of mind.
Who We Serve
Proudly protecting families, homes, and businesses across Boston’s neighborhoods—from the city skyline to the tree-lined streets of West Roxbury.
Homeowners & Condo Owners
In Hyde Park, Dorchester, South Boston, and surrounding areas—coverage that protects your home’s value and the life you’ve built inside it.
Renters
In West Roxbury, Roslindale, Mattapan, and nearby communities—affordable peace of mind for what matters most.
Drivers
From Jamaica Plain to Quincy—auto insurance designed for Boston’s streets, commutes, and local driving realities.
Small Businesses
Across Jamaica Plain, South End, Milton, and beyond—coverage that supports local entrepreneurship and neighborhood growth.
Growing Families
Wherever life takes you in the region—guidance for life’s transitions, now including financial planning.
Local Agents, Real Relationships, Better Coverage
At James W. Hennigan Insurance Agency, we know that insurance isn’t just about protection—it’s about people. That’s why we combine real-world experience, responsive service, and deep community knowledge to help you make confident, informed choices.
From our West Roxbury office, we proudly serve individuals, families, and small businesses across Boston neighborhoods like Roslindale, Hyde Park, Jamaica Plain, and South Boston—offering personalized solutions, clear advice, and coverage that reflects the needs of each client we serve.
