Rooted in a tradition of protecting what matters most - your family, your home, and your business.
01/06/2026
As we step into 2026, it's the ideal time to review your insurance coverage to align with your new year goals.
If you currently have homeowners insurance through O'Grady Insurance, bundling it with an auto policy might be a wise choice. Not only could this simplify your coverage, but it might also lower your premiums.
Interested in exploring your options? We're here in Plymouth, ready to assist with a complimentary quote. Start your year strong with the right coverage and savings!
01/02/2026
If you have an auto policy, bundling it with homeowners insurance could mean:
✔️ Fewer bills to manage
✔️ Potential savings
✔️ One point of contact for both policies
Interested? Give us a call today if you’d like to explore bundling options for the year ahead.
12/30/2025
The holidays may bring surprises, but insurance coverage gaps don't have to be one of them! 🎉
As the year wraps up, it's an ideal time to review your insurance needs—especially if you've welcomed a new family member, bought a new home, or switched jobs. A quick check-in can ensure you greet the new year with confidence.
Need guidance or a coverage review? Call us at O'Grady Insurance. We're here to make the process seamless.
Wishing you a joyful and safe holiday season from your Plymouth neighbors!
12/22/2025
As we close out the year, the team at O'Grady Insurance is sending warm wishes to our Plymouth community and beyond. May this season bring you peace, joy, and the perfect moments to recharge with your loved ones.
Please note, our office will be taking a short break to celebrate from December 24th to 26th and again from January 1st to 2nd. We'll be back ready to serve you with all your insurance needs.
Here's to a joyful holiday season and a safe, prosperous start to 2026!
12/18/2025
A beautifully decorated tree is a holiday highlight, but it also presents real fire risks if not handled with care. Ensure your festive tree is a source of joy and not danger by following these safety tips:
- **Placement:** Keep your tree away from heat sources like fireplaces and heaters.
- **Electrical Caution:** Only use lights that are in good condition. Never connect more than three strings of lights and avoid using candles as decorations.
- **Maintenance:** Water your tree daily to prevent it from drying out, which significantly reduces fire risk.
Here's to a bright and safe holiday season for all! If you have any questions or need assistance, give us a call. 🎄✨
12/04/2025
🎉 Hosting friends and family this holiday season in Plymouth? Make sure to review your homeowners insurance before the festivities kick off. Holiday gatherings can come with unexpected risks, and we're here to help you turn cheer into peace of mind, not chaos.
Swipe through for holiday hosting tips and potential risks to keep in mind. A quick policy check can make all the difference.
Need to chat about your coverage? We’re ready to help ensure your holidays are joyful and worry-free. Call us today with any questions!
11/27/2025
Gratitude is central to O'Grady Insurance, and this Thanksgiving, we're especially thankful for our incredible clients and community in Plymouth and the South Shore.
Whether you're traveling, preparing a feast, or relaxing with family, we hope your holiday is filled with joy and everything you cherish.
Please note: Our office will be closed on Thursday, November 27th, and Friday, November 28th, to let our team enjoy the holiday.
Wishing you and your loved ones a warm, safe, and memorable Thanksgiving!
11/19/2025
As winter approaches, it's time to prepare your home to avoid common cold-weather insurance claims. ❄️
Here are some easy, proactive tips to help protect your home:
- Set your smart thermostat for energy efficiency
- Clean out those gutters to prevent ice dams
- Check your home's insulation to keep the cold out
Have questions about coverage as we head into winter? We're here to help. Contact O'Grady Insurance for peace of mind this season. 🌨️
11/11/2025
This Veterans Day, O'Grady Insurance takes a moment to honor and express our profound gratitude to all veterans and their families. Your sacrifice, strength, and dedication are immeasurable, and we deeply appreciate your service.
Living and working in Plymouth, we understand the importance of community and the everyday heroes among us. If you're a veteran or have one in your life, we hope today brings the recognition and appreciation you deserve. Thank you for your unwavering service. 🇺🇸
11/04/2025
Planning some winter adventures with your snowmobile or UTV in Massachusetts? ❄️ Don't forget to secure one crucial piece of gear: insurance. Here's what you need to know:
✅ Liability Coverage - Essential for public trails; covers damage or injuries to others.
✅ Collision Coverage - Helps with repairs if your vehicle hits another object.
✅ Comprehensive Coverage - Protects against theft, weather, and wildlife.
✅ Medical Payments Coverage - For medical expenses, no matter who's at fault.
✅ Accessories & Gear Protection - Covers custom parts and personal items.
Most homeowners policies won't cover off-road vehicles off your property. As your local Plymouth insurance agency, we're here to ensure your winter toys are protected. Contact O'Grady Insurance today for a quote or to start your policy!
10/31/2025
This Halloween, our team just wanted to share a little festive cheer with our clients: It’s truly 🍬 a treat 🍬 to work with you!
Whether you're carving pumpkins, dressing up, or enjoying time with friends, we hope your Halloween is full of fun — and free of tricks.
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Established by James O’Grady in 1971 , O’Grady Insurance Agency began as an Allstate sales center. Jim; as he was fondly referred to, then took a step into independent agency ownership in 1989. As a family owned and operated agency Jim built his business from the ground up, with clients just like you. Hard working people who valued the relationship between agent and insured. It is the very foundation of the service we provide today. Making sure that your insurance needs are met with our expertise and service standards.
In 2003 Patrick O’Grady joined his father in what is now a leading agency in the Plymouth area. Patrick brought many more years of experience and a knack for client service. A graduate of Syracuse University he worked in New York for a few years before returning home to be a partner in his family business. Patrick now resides on the South Shore with his wife Shey and their children and is an active member of his children’s sports teams and his community.
Maureen Watson joined the O’Grady family team in 1989 as a licensed agent and has been a dedicated team member ever since. She brings many years of experience and as our clients say - she is simply the best!
Leigh-Ann Silva came to O’Grady in 2019. She brought with her many years of insurance experience having worked in health insurance for over 15 years. She is a licensed agent and is the perfect addition to our motley crew!
In an industry as large and complex as insurance it is important that your agent understand your individual needs, and provide the best and most comprehensive coverage for your home, auto, or commercial policies. We strive to provide world-class customer service while remaining your most trusted partner for your most valued assets.
In 2018 Jim, sadly passed away, leaving quite a legacy and it is our promise to you to continue that legacy by ensuring we meet that same standard of service that Jim instilled in our agency many years ago.
We encourage you to call us, or stop by for a quote. It is our pleasure to serve you.
