When it comes to safeguarding what matters most, finding the right partner is essential. For over eight decades, O’Grady’s Insurance has been a trusted name in Windsor and Essex County. With a 4.8/5 average Google rating from 35+ reviews, their commitment to excellence speaks for itself.
Since 1936, this multi-generational agency has provided tailored solutions for homes, vehicles, businesses, and specialty assets. Their team takes pride in explaining policies in plain language, ensuring you fully understand your coverage. As one client, John Skelton, shared, their family-friendly touch sets them apart.
Whether you’re looking for auto, homeowners, or business coverage, O’Grady’s Insurance is ready to meet your needs. Call today to customize a policy that fits your unique situation. With their local expertise and personalized service, you can feel confident your assets are in good hands.
Key Takeaways
- Trusted partner for comprehensive asset protection since 1936.
- 4.8/5 average Google rating from 35+ reviews.
- Customizable policies for homes, vehicles, and businesses.
- Family-friendly service with clear, plain-language explanations.
- Local experts serving Windsor and Essex County communities.
Why Choose O’Grady’s Insurance for Your Needs?
Finding the right coverage for your unique needs can feel overwhelming, but it doesn’t have to be. With decades of experience and a commitment to personalized service, we’re here to simplify the process and ensure you’re fully protected.
Tailored Insurance Solutions
Every client is different, and so are their needs. Whether you’re insuring a family home, a business, or a specialty asset, we design policies that fit your specific situation. For example, James Fitzpatrick’s farm insurance was customized to cover his unique risks, providing peace of mind without unnecessary costs.
We also offer multi-policy discounts and annual coverage reviews to ensure your protection evolves with your life. As Kenda Metcalf shared, “They saved us money on homeowners and car insurance while keeping us fully covered.”
Years of Experience and Expertise
With over 80 years of combined industry experience, our team brings unmatched knowledge to every interaction. Brittany’s expertise in seamless policy transitions, as highlighted by Tonya Edwards, ensures a smooth experience for clients.
Our agents hold specialized certifications like CPCU and CRM, ensuring you receive professional advice. Tim’s hands-on claims assistance for Kyleigh Falcone’s total loss wreck is just one example of our dedication to supporting you when it matters most.
We’re also available for weekend and evening consultations, making it easy to get the help you need. As Lori Kernik noted, “Their 24/7 availability for policy concerns gives me confidence I’m always covered.”
Our historic partnerships with local businesses, like Poirier Electric since 1945, reflect our deep roots in the community. We take pride in preventing over- or under-insurance scenarios through thorough needs analysis.
Comprehensive Insurance Services Offered by O’Grady’s
Your assets deserve coverage that adapts to your lifestyle and goals. Whether you’re protecting your car, home, or business, we provide tailored solutions to meet your needs. Our services are designed to offer peace of mind while ensuring you’re fully protected.

Auto Insurance Coverage
Finding the right auto insurance plan is essential for your safety and financial security. We offer a range of options, from liability to full coverage, ensuring you’re protected on the road. Usage-based discounts and teen driver programs help you save while maintaining comprehensive protection.
Here’s a quick comparison of liability vs. full coverage:
| Feature | Liability Coverage | Full Coverage |
|---|---|---|
| Accident Protection | Covers damages to others | Covers damages to others and your vehicle |
| Cost | Lower premiums | Higher premiums |
| Best For | Drivers with older vehicles | New or high-value vehicles |
Homeowners Insurance Policies
Your home is your sanctuary, and our homeowners insurance policies ensure it stays protected. We offer options like replacement cost and actual cash value, so you can choose what works best for your budget. High-value items like jewelry or art can also be covered with specialized endorsements.
As Dixie Selmon shared, “Policy optimization saved me hundreds while keeping my home fully covered.” Our team is here to help you find the right balance between cost and protection.
Business Insurance Options
Running a business comes with unique risks, and our business insurance options are designed to address them. From industry-specific packages for contractors and medical practices to cyber liability coverage, we’ve got you covered. Commercial auto insurance is also available for fleets, ensuring your vehicles are protected.
For farms and agricultural businesses, we offer specialized solutions tailored to your needs. Our 24/7 claims reporting via app or phone ensures you’re supported whenever you need it.
Benefits of Partnering with O’Grady’s Insurance
Protecting your assets requires more than just a policy—it demands a trusted partner. With decades of experience and a focus on client satisfaction, we’re here to make sure you get the best value and support.

Competitive Rates and Flexible Policies
We understand that everyone’s financial situation is different. That’s why we offer competitive rates that often beat national carriers. Our flexible payment options include annual, quarterly, and monthly plans to fit your budget.
Life changes like marriage, home renovations, or career shifts? We’ll help you convert your policy to match your new needs. As Dixie Selmon shared, “They saved me money while keeping me fully covered!”
Personalized Advice and Support
Our team provides tailored advice to ensure you’re making the best decisions for your coverage. With an average of 12 years of experience, our agents are here to guide you every step of the way.
We also offer bilingual services for ESL clients and quarterly policy reviews to keep your protection up-to-date. As Susan Burris noted, “They’re always ready to help!”
Customer-Centric Approach
Your satisfaction is our priority. Our claims advocacy program gives you direct access to adjusters, and we guarantee a 72-hour resolution for most claims. Long-term clients enjoy VIP service tiers for added perks.
Roseann Falcone’s smooth claims experience is just one example of our commitment to exceptional service. Call today to see how we can meet your needs.
- Compare premium savings against national carriers.
- Policy conversion for life changes like marriage or renovations.
- Bilingual service options for ESL clients.
- Quarterly policy review appointments.
- Claims advocacy program with direct adjuster access.
- 72-hour claims resolution guarantee.
- VIP service tier for long-term clients.
- Payment flexibility: annual, quarterly, or monthly.
Conclusion: Secure Your Future with O’Grady’s Insurance
Securing your future starts with the right protection plan. Our team is available 24/7 to assist with policy changes, ensuring your coverage always meets your needs. With a 98% client retention rate, we’re proud to serve communities beyond Windsor and Essex.
We offer mobile notary services for after-hours signings and encourage you to schedule a free coverage audit today. As Tim shared in his review, we strive to be “like a good neighbor”, always ready to help.
Our community involvement and sponsorships reflect our commitment to giving back. Plus, multi-policy discounts make it easier to protect your home, business, and more. Call now to start your journey—consultation, customization, and coverage are just a step away.
As Tiffany Bumgardner noted, “Their holiday-week responsiveness was amazing.” Let us show you why so many trust us with their protection needs.
FAQ
What types of coverage does O’Grady’s Insurance offer?
I provide tailored solutions for auto, homeowners, and business insurance. Whether you need protection for your car, home, or company, I’ve got you covered.
How does O’Grady’s Insurance customize policies for my needs?
I take the time to understand your unique situation and offer flexible options to ensure your coverage fits perfectly. My goal is to protect what matters most to you.
Can I get competitive rates with O’Grady’s Insurance?
Absolutely! I work hard to provide affordable rates without compromising on the quality of your coverage. You’ll get great value for your investment.
What makes O’Grady’s Insurance different from other providers?
With years of experience, I focus on personalized advice and a customer-centric approach. My priority is to support you every step of the way.
How do I get started with O’Grady’s Insurance?
It’s simple! Just reach out to me today, and I’ll guide you through the process of finding the right policy for your needs.
