Finding the right insurance company in Windsor can feel like a full-time job. Between unpredictable weather, cross-border traffic, and changing rates, it pays to work with a broker who knows your neighbourhood—and answers the phone when you call.
To make your search easier, we’ve rounded up five of the best Windsor insurance companies for 2026. Whether you’re protecting your first car, your home, or your growing business, these local experts stand out for their service, expertise, and community roots.
1. Experia Group: Best for Personalized, High-Value Coverage
Experia Group is a boutique insurance brokerage based in Windsor, offering a distinctly personal approach to coverage. Their advisors take the time to understand each client’s needs, providing solutions tailored to their lifestyle and priorities.
From luxury homes and vehicles to watercraft, RVs, and valuable collections, Experia specializes in protecting high-value assets. Their concierge-style service and focus on detail make them a top choice for professionals, entrepreneurs, and families who value attentive, customized coverage.
Why they stand out: Personalized service, high-value protection, and deep local knowledge.
2. All-Risks Insurance Brokers: Comprehensive Coverage Options
With a strong presence in Windsor and across Ontario, All-Risks Insurance Brokers combines local service with national reach. They work with a wide range of insurers to offer competitive rates for home, auto, business, and specialty insurance.
Clients appreciate the ability to bundle policies and simplify the process, providing efficient, full-spectrum coverage from a single source.
Why they stand out: One-stop convenience for families or business owners who want comprehensive coverage.
3. Tabone Insurance Brokers: Family-Focused Service
Tabone Insurance Brokers is a long-established, family-owned and operated business serving the Windsor-Essex region. Their reputation is built on trust, accessibility, and straightforward advice.
Working with Tabone means dealing directly with a broker who knows your file—not a call centre. They offer a full range of personal and commercial insurance, with a focus on building lasting relationships.
Why they stand out: Local, family-run service and genuine personal attention.
4. Billyard Insurance Group: Digital Convenience
Billyard Insurance Group is one of Ontario’s fastest-growing brokerages, known for its modern, digital-first approach. The Windsor branch offers online quotes, virtual consultations, and a smooth process for managing multiple types of coverage.
They offer a wide range of policies, including auto, home, life, travel, and business, making them a great fit for customers who prefer speed and accessibility.
Why they stand out: Tech-driven convenience with full-service coverage options.
5. Spadafora Insurance Services: Business and Property Coverage Experts
Spadafora Insurance Services is a locally owned brokerage with deep roots in Windsor. They specialize in rental property, commercial, and personal insurance, offering practical solutions tailored to the local market.
Their focus on responsive support and client relationships has earned them a loyal customer base, particularly among landlords and small business owners.
Why they stand out: Dedicated service for Windsor’s business community and property owners.
Tips for Choosing the Right Insurance Company in Windsor
Choosing the right insurance partner depends on your situation and priorities. Before you decide, it’s worth keeping a few things in mind:
- Compare at least three quotes—rates and options can vary significantly.
- Ask about flood and water-damage coverage, which is especially relevant in Windsor.
- Confirm that your broker has local expertise; they’ll better understand area-specific risks.
- Check customer reviews and ask about claims support and response times.
Final Thoughts
Windsor’s insurance market offers a strong mix of local expertise and national resources. Whether you prefer a boutique experience or a large, full-service brokerage, there’s an option to match your needs.
As we head into 2026, Experia Group continues to stand out for its personal approach, premium protection options, and commitment to clients throughout the Windsor-Essex region. Windsorites can contact Experia Group for help with all their insurance needs.