Finding the best insurance agency in Massachusetts means looking past a single quote and asking who will actually be there when you need them — for a claim, a coverage question, or a policy review five years down the road. Massachusetts has roughly 1,650 independent insurance agencies statewide, so narrowing the field takes more than a Google search.
We reviewed six established, independently owned Massachusetts insurance agencies — including our own — using verified Google ratings, BBB standing, Trusted Choice membership, carrier access, and staff certifications. We intentionally kept this list to independent agencies: no bank-owned or credit-union-affiliated insurance divisions, since those operate under a different ownership structure than a traditional independent agency. This is an editorial comparison, not a paid ranking, and we're publishing the numbers as we found them, including where they don't put us in first place.
How We Evaluated the Best Massachusetts Insurance Agencies
● Independently owned (no bank or credit union affiliation)
● Verified Google review ratings and review volume (checked July 2026)
● Better Business Bureau (BBB) rating and accreditation status
● Trusted Choice network membership
● Access to multiple insurance companies (carrier count, where published)
● Professional staff certifications (CIC, CPCU, CISR, CPIA, and similar)
● Years serving Massachusetts communities
● Independent industry recognition (Best Practices Agency, Five Star Accreditation, and similar)
This is an editorial comparison, not an official industry award. Google ratings, BBB ratings, and review counts reflect a snapshot at the time this article was written and will change over time. As with our SouthCoast-focused comparison, Yelp and Facebook were checked but excluded as ranking factors — neither carries meaningful, consistent review volume for Massachusetts insurance agencies compared to Google.
1. Berry Insurance — Franklin, MA
Google rating: 5.0 stars (586 reviews) | Best for: Personal and commercial insurance with a strong educational, client-first approach
Credentials: BBB rating: A+ · third-generation, family-owned since 1922 · Trusted Choice membership and carrier count not publicly itemized
Berry Insurance leads this list on the numbers: the highest Google rating of the group, tied with two others, and by far the largest review volume at 586. Founded in 1922 by Johanna Berry as a "kitchen broker" working out of her home, the agency is now in its third generation and widely known in the insurance industry for its content-driven, education-first approach to client relationships. Berry writes personal and commercial insurance — auto, home, renters, business, and workers' compensation — across Massachusetts and New England.
2. Richardson Insurance — Hanover, MA
Google rating: 5.0 stars (343 reviews) | Best for: South Shore homeowners and families wanting a modern, responsive independent agency
Credentials: BBB rating: A+ · family-owned since 1930 (95 years) · Trusted Choice membership and carrier count not publicly itemized
Richardson Insurance has served Hanover and the South Shore since 1930, currently run by the third generation of the Richardson family. It ties for the top Google rating in this comparison, backed by a strong 343-review base. The agency emphasizes a tech-forward, communication-flexible approach — text, email, or phone — alongside traditional personal lines like home, auto, and life insurance.
3. HCC Insurance — New Bedford, MA
Google rating: 5.0 stars (242 reviews) | Best for: Businesses, apartment complex owners, and contractors wanting hands-on risk management — with added depth in coastal home and flood coverage
Credentials: 30+ carriers represented · 6 staff hold industry certifications (CIC ×2, CPIA ×3, CISR ×1) · Trusted Choice member · BBB rating: A+ · 2025 & 2026 IIABA Best Practices Agency
That's us. HCC ties for the highest Google rating in this statewide comparison, though with a smaller review base than Berry or Richardson — a fair, honest number worth stating plainly. Where HCC stands out is depth of documentation: a publicly listed carrier lineup of 30+ companies, six staff holding recognized industry certifications, and a 2025 & 2026 Best Practices Agency designation from the Independent Insurance Agents & Brokers of America (IIABA) and Reagan Consulting — a national, third-party benchmark awarded to a small percentage of nominated agencies. Founded in 1926 and now run by the third generation (soon to be 4th) of the same family, HCC specializes in coastal home insurance, flood coverage, and contractor/business risk management for the SouthCoast region and beyond. Licensed in MA, RI, CT, NH & ME.
4. Vargas & Vargas Insurance — Dorchester, MA
Google rating: 4.9 stars (743 reviews) | Best for: Greater Boston families and multi-unit property owners
Credentials: BBB rating: A+ · Trusted Choice member · family-owned for over 40 years · carrier count and staff certifications not publicly itemized
Vargas & Vargas Insurance has the largest review volume of any agency in this comparison by a wide margin — 743 Google reviews — though its 4.9 rating places it just below the three 5.0-rated agencies above. Based in Dorchester and serving Greater Boston since the early 1980s, the agency is well known among triple-decker and multi-family property owners for navigating Massachusetts-specific coverage challenges, and is licensed to serve clients statewide.
5. Ormsby Insurance Agency — West Springfield, MA
Google rating: 4.8 stars (171 reviews) | Best for: Western Massachusetts and Pioneer Valley families and drivers
Credentials: Trusted Choice member · Five Star Agency (one of only 26 in Massachusetts, per the Massachusetts Association of Insurance Agents) · BBB: Not Rated (insufficient information on file) · family-owned since 1969 (57 years) · carrier count and staff certifications not publicly itemized
Founded in 1969 by Richard S. Ormsby and now based in West Springfield, Ormsby Insurance is one of the stronger independent options in Western Massachusetts, serving the Pioneer Valley and northern Connecticut. It holds the Massachusetts Association of Insurance Agents' Five Star designation — an honor limited to just 26 agencies statewide — alongside Trusted Choice membership. Its BBB profile shows no letter-grade rating (the Bureau notes insufficient information on file, not a negative mark), which is worth knowing if BBB history factors into your decision.
6. Deland, Gibson Insurance Associates — Wellesley Hills, MA
Google rating: 4.8 stars (52 reviews) | Best for: Businesses and families wanting a larger, multi-office agency with deep institutional backing
Credentials: BBB rating: A+ · Trusted Choice member · Five Star Accredited (Massachusetts Association of Insurance Agents) · Assurex Global Partner · family-owned since 1900 (126 years) · 20+ carriers represented
Deland, Gibson has the longest operating history in this comparison — founded in 1900, now in its fourth generation — and arguably the deepest institutional credentials: it's the largest independently owned property & casualty agency headquartered in Massachusetts by premium volume (Boston Business Journal), a Five Star Accredited agency, and a member of Assurex Global, a network of leading independent agencies worldwide. Its Google review base is the smallest in this comparison, though matched in rating by Ormsby above it on the review-count tiebreaker. With six offices across the state, it's a solid fit for larger businesses and families wanting broader bench strength.
Comparison at a Glance
Rank | Agency | Location | Google Rating | Reviews | BBB | Trusted Choice | Serving Since |
1 | Berry Insurance | Franklin | 5.0 | 586 | A+ | Not confirmed | 1922 |
2 | Richardson Insurance | Hanover | 5.0 | 343 | A+ | Not confirmed | 1930 |
3 | HCC Insurance | New Bedford | 5.0 | 242 | A+ | Yes | 1926 |
4 | Vargas & Vargas Insurance | Dorchester | 4.9 | 743 | A+ | Yes | Early 1980s |
5 | Ormsby Insurance | West Springfield | 4.8 | 171 | Not rated | Yes | 1969 |
6 | Deland, Gibson Insurance | Wellesley Hills | 4.8 | 52 | A+ | Yes | 1900 |
Ranked primarily by Google rating, with review count as a tiebreaker among equal ratings — the same methodology used across our agency comparisons. "Not confirmed" means we found no public Trusted Choice directory listing for that agency, not that one doesn't exist. Ormsby's BBB profile shows "Not Rated" rather than a letter grade, meaning the Bureau has insufficient information on file — not a negative finding.
Google Ratings Across Massachusetts Agencies
How Long Each Agency Has Been in Business
Vargas & Vargas Insurance (40+ years) is not shown above — it cites an approximate history rather than a single confirmed founding year.
A Note on This Ranking
We built this comparison the same way we built our SouthCoast-specific one: Google rating first, review volume as a tiebreaker, then BBB, Trusted Choice, carrier access, and staff certifications layered in as context. At a statewide level, that methodology puts Berry Insurance and Richardson Insurance ahead of HCC on the primary metric — both have a larger, equally perfect-rated review base than we do. We think that's worth saying plainly rather than reshuffling the criteria to land differently. Where HCC holds its own is in the depth of what's publicly documented: carrier count, certified staff, and a national Best Practices Agency designation — real differentiators, just not ones that outweigh a bigger five-star review base.
All six agencies on this list are legitimate, well-reviewed, independently owned options — the right one for you likely comes down to location, the type of coverage you need, and whether you want a smaller local office or a larger multi-office agency. If you're comparing options for coastal Massachusetts home insurance, flood coverage, or contractor risk management, we'd be glad to talk. For businesses or families elsewhere in the state, any of the agencies above are worth a call.
Ready to Discuss Your Insurance? Find out the HCC Difference!
Honestly, It's the Best Policy.
HCC Insurance Agency
195 Kempton Street, New Bedford, MA
Phone: (508) 997-3321
Email: info@hccinsuranceagency.com
Web: hccinsuranceagency.com
The Friendly Insurance Office. More Than a Policy. A Partner in Risk Management.
This article is provided for general informational purposes only and does not constitute insurance, legal, or financial advice. Coverage details, carrier availability, certifications, and agency offerings are subject to change; Google ratings, BBB ratings, and review counts were current as of July 2026 and will change over time. Contact each agency directly to confirm current information. HCC Insurance Agency is not affiliated with the other agencies listed and makes no guarantee as to the accuracy of third-party business details cited here.