James W. Hennigan Insurance Agency

A Century of Coverage, Protecting Homes, Automobiles, and Businesses Since 1926

#1 Trusted coverage, personal service, and deep local roots—built on three generations of expertise.

Trusted Service. Competitive Rates.

Decades of care. Deep local roots.

For nearly a century, Hennigan Insurance has served families and businesses across West Roxbury and surrounding Boston neighborhoods with integrity, care, and personal attention.



As a third-generation, family-owned agency, we take pride in knowing our clients by name—not policy number. From Hyde Park homeowners to South Boston condo owners and Roslindale small businesses, we deliver thoughtful advice and reliable coverage shaped by the needs of each neighborhood we serve.

A red and white building with a sign that says i am a princess - Office of the Hennigan Insurance in West Roxbury and surrounding boston neighborhoods.

Home Insurance

Tailored protection for Boston homes and everything in them.

A black and white icon of a house with a shield and hands.

Auto Insurance

Stay covered on city streets and neighborhood roads.

A black and white icon of a car with a shield and a check mark on it.

Renters Insurance

Affordable coverage for apartment dwellers and city renters.

A black and white drawing of a house with a key on a shield.

Condo Insurance

Smart coverage for condo owners and associations alike.

A black and white drawing of a building with a shield on it.

Business Insurance

Safeguarding the shops, services, and local ventures that power Boston.

A black and white drawing of a briefcase , coins and an umbrella.

Have questions?

We’re here to help you find the right insurance coverage with clear, personal guidance.

A black and white icon of a clipboard , a clock , a dollar sign , and a pen.

Insurance that’s honest, local, and built to serve your needs.

Insurance isn’t just what we do—it’s how we serve. At James W. Hennigan Insurance Agency, every policy starts with a conversation. Our team brings decades of experience, passed down through three generations, to help you make confident, informed decisions.


With deep knowledge of Boston neighborhoods, personalized attention, and access to competitive rates from trusted carriers, we deliver clear, reliable coverage that fits your life—without the runaround.

About James W. Hennigan Insurance Agency

Not Just Your Agents—Your Insurance Partners 

Why Choose Us?

At James W. Hennigan Insurance Agency, our approach is built on personal service, professional guidance, and a deep understanding of the communities we serve. We don’t believe in one-size-fits-all policies or pushy sales tactics—just honest advice, responsive support, and solutions that make sense for your life and your budget.


What makes us different?


  • Competitive rates from trusted local carriers
  • Responsive team with deep Boston expertise
  • Generational service backed by experience
A man in a blue shirt and tie is holding a binder with papers in it.

What Makes Us Different?

At James W. Hennigan Insurance Agency, our team brings deep knowledge of Boston’s neighborhoods, competitive rates from respected regional carriers, and a commitment to helping you find coverage that fits—clearly and confidently.


We're not just in West Roxbury—we're part of it. And if you’ve driven by our office, you’ve probably seen the 1931 Model A Ford parked out front. It doesn’t get great mileage, but it’s a great reminder that we’ve been doing this a long time—and we’re here for the long haul.

A group of people standing next to each other on a white background.

Family-run and deeply involved in the Boston community

A pair of hands holding a dollar sign in their hands.

Competitive rates through MAPFRE, Quincy Mutual, Norfolk & Dedham

A black and white icon of a map with a house and a pin.

Local claims support—even after hours