About Us

Why Work with MacCallum Group?

At MacCallum Group, we believe insurance should be straightforward, customized, and rooted in trust. Whether you’re a first-time homeowner, a growing business, or someone comparing quotes for the first time in years—we meet you where you are.

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About Our Team

Rob MacCallum

Rob MacCallum is the principal owner of MacCallum Group and brings over ten years of experience in the insurance industry—along with a strong belief that personalized service still matters.

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Local Insight, Real Relationships

We live and work in the same communities you do—from Weymouth to Norwell and across the South Shore. You’re not calling a call center—you’re calling your neighbor.

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Bilingual Support in English and Portuguese

Protect your home and everything in it with our home insurance plans, designed to cover property damage, liability, and personal belongings.

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Customized Policies for Real Lives

No two households or businesses are the same. That’s why we take the time to understand your goals and tailor policies to match—whether it’s for your vehicle, your home, or your company.

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Experienced, Not Pushy

With over a decade of insurance knowledge, we know how to guide you—but we never pressure you. Our job is to protect, not oversell.

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Responsive and Reliable

When something goes wrong, you don’t want to wait. Our clients count on us for quick answers, thoughtful guidance, and support when they need it most.

Get a Quote Today

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Whether you’re shopping for home insurance in Weymouth, looking to protect your business, or simply want to understand your options—we’re here to help.

Our Reviews

Antonio C.

Very nice people

Mark H.

A Philosopher once wrote; you need three things to have a good life. One, a meaningful relationship. Two, a decent job of work and Three, to make a difference. Well, this company have 2 and 3 nailed. Keep it up guys. Would recommend them to anyone. Nice to do business with good, honest people who care.

Colleen C.

The best insurance company I have ever been with. Both Rob and Claudia are personable and knowledgeable and will work with you towards finding the policy that best suits your needs. I have told all my family and friends, you will not disappoint!

Juliana S.

I've been with this company for years, I love the service and they solve everything I need! They are attentive and wonderful!

Amanda R.

I’ve had many greats experiences working with The MacCallum Group. They’ve been professional, responsive, and genuinely helpful every step of the way. It’s clear they care about their clients and take the time to ensure everything is handled thoroughly and efficiently. I truly appreciate their support and would highly recommend them to anyone looking for a reliable and knowledgeable team.

Rose C.

I don't have enough words to express how happy i am with the group! Claudia is amazing! Lucas and Caroline are always so helpuful, even with small details any auto owner should be able to do it them self! Thank you Claudia, Lucas & Caroline!

Mark S.

Rob and Claudia did a great job on my insurance policies. The level of service and professionalism is fantastic. Very nice to see in a world of faceless online carriers.