Auto InsuranceBusiness Insurance
Henry & Matthews Insurance
Excellent
363 Willow Crescent, Orangeville, ON M9A 7I5
Profile last updated: February 20, 2026
Est. 1998 5-10 team members
3.2
At Henry & Matthews Insurance, we believe that great insurance starts with great relationships. Based in Orangeville, Ontario, our brokerage takes pride in offering personalized insurance solutions tailored to each client's unique situation. We represent multiple top-rated insurance companies, which means we can find you the best coverage at the most competitive price.
Our services include personal lines such as auto, home, condo, and tenant insurance, as well as commercial lines including general liability, commercial property, professional liability, and more.
With 28 years of experience serving our community, we have built strong relationships with insurers and a deep understanding of our clients' needs. Let Henry & Matthews Insurance be your advocate in the insurance marketplace. Contact us today for a free, no-obligation quote.
Contact Information
Location
363 Willow Crescent
Orangeville, ON M9A 7I5
Location Map
363 Willow Crescent, Orangeville, ON M9A 7I5
Get DirectionsInsurance Lines
Auto InsuranceHome Insurance
Specialties
Senior DriversProfessional Liability
Business Hours
SundayClosed
Monday08:30 - 17:00
Tuesday08:30 - 17:00
Wednesday08:30 - 17:00
Thursday08:30 - 17:00
Friday08:30 - 16:00
SaturdayClosed
Languages
English
Photos
Reviews
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3.2
6 reviews
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T
Tyler Chen
Jan 2026
Great for home insurance
Bought our first home and Henry & Matthews Insurance walked us through everything we needed for home insurance. They even bundled it with our auto policy for extra savings.
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T
Thomas Ross
Nov 2025
Personal touch
What I love about Henry & Matthews Insurance is the personal service. They remember my name and proactively reach out before renewal to review my coverage.
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P
Priya Robertson
Oct 2025
Would not recommend
Had a bad experience with Henry & Matthews Insurance. When I needed to file a claim, they were hard to reach and unhelpful. Ended up switching to a different broker.
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N
Nicole Schmidt
May 2025
Room for improvement
Henry & Matthews Insurance handled our business insurance, but the process was slow and I had to follow up multiple times. The final policy was fine though.
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N
Noah Okafor
Mar 2024
Trustworthy and reliable
I've trusted Henry & Matthews Insurance with all my insurance needs for the past five years. They always review my policies at renewal to make sure I'm getting the best deal.
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J
Julie Pelletier
Mar 2024
Average experience
My experience with Henry & Matthews Insurance was average. They found decent auto insurance rates but nothing spectacular. Communication could be improved.
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