What We Do

Why Bailey Howes Insurance?

We Take a Holistic Approach to Risk Management

At Bailey Howes, we take the time to look at the full picture of your life, not just individual policies. Our team works to understand your family, lifestyle, assets, and long-term goals so we can design a protection plan that aligns with your priorities and the value of what you’ve built.

From your primary residence and secondary properties to your vehicles, collections, and overall net worth, we focus on identifying potential gaps in coverage, minimizing risk, and safeguarding the assets that define your success. Our goal is to help you confidently select a comprehensive insurance strategy that protects every aspect of your distinctive life.

What You Can Expect from Us

We are committed to providing an exceptional insurance experience for every client we serve.

Regular assessments of your insurance requirements.

We go beyond reviewing core assets such as your property and vehicles. By understanding every dimension of your evolving life, including your health, lifestyle, and community involvement, we proactively identify potential exposures before they become risks. This forward-looking approach allows us to keep your coverage aligned with your needs today and into the future.

Service and support throughout your life’s journey.

Whether you are relocating within Massachusetts, acquiring property out of state, or traveling abroad, you can depend on the Bailey Howes team for expert guidance every step of the way. Our professionals are committed to helping you protect your family, assets, and lifestyle with seamless service wherever life takes you.

Empowering you to make informed decisions.

Your time is valuable, and we strive to make the insurance process as straightforward and stress-free as possible, even when addressing complex risks. Our team provides thoughtful recommendations to eliminate coverage gaps and overlaps, secure competitive rates, and safeguard the people and assets you value most, so you can make confident, informed decisions.

Tailored solutions for your unique needs.

Through long-standing relationships with leading national and regional insurance carriers, Bailey Howes Insurance gives you access to a broad range of specialized and customizable coverage options. Every solution is tailored to fit your goals and lifestyle, from personal protection to complex risk management programs.

Collaboration with your wealth management team.

We work alongside your trusted financial and legal advisors to create a coordinated strategy for comprehensive protection. Whether you require insurance for your home, watercraft, investments, or business ventures, or need life, disability, or long-term care coverage, our team integrates each element into your overall wealth management plan.

Personal and prompt responses, always.

With Bailey Howes Insurance, you can expect attentive service, clear communication, and ongoing support. Our team is always within reach as your life evolves and your insurance needs change. Call, email, or text us anytime, and you will hear back quickly from a knowledgeable, familiar professional who knows you and your coverage.

Hear From Our Clients

What Makes the Bailey Howes Insurance Experience Different?

    
 
 
       Posted on Google  
   
   Lee-Ann Norman 
 8 September 2025
 
 
 Trustindex verifies that the original source of the review is Google. Catherine Washington is excellent to work with!  She has helped me with my personal insurance questions as well as preparing to open a business questions.
  
 
      Posted on Google  
   
   Anders Beer 
 26 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. I have had nothing but good experiences with Howes insurance group. Greg Howes, Traci Madigan, and Mike Umano were all really responsive and articulate when it came to finding the right insurance and answering questions regarding home, umbrella, and auto policies.

I have had plenty of questions for all of the people I named, and every one of them has been really insightful and articulate. Most recently I asked about those consumer insurance policies that are often sold by retailers and what differentiates them from the coverage under our homeowners policy. Mike was kind enough to go into detail about it and I really appreciated his objective breakdown on how the coverage works.

Keep up the fine work, Howes Insurance Group :)
  
 
      Posted on Google  
   
   Robert Stemple 
 18 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. Over 30 years of helpful, quick answers. They treat you as friends not customers😀👍👍👍
  
 
      Posted on Google  
   
   Roger Beatty 
 4 December 2024
 
 
 Trustindex verifies that the original source of the review is Google. Howes is a small agency staffed with highly knowledgeable insurance professionals -- they're large enough to attract and retain experienced pros, and small enough to ensure personal contact in all business interactions. No voice mail maze, no call center, no chatbots -- they'll answer the phone directly, or call you back same day. When I call, I usually reach somebody I already know on my first attempt. I've been with them for years, and they've always done a great job.
  
 
      Posted on Google  
   
   Irwin Hipsman 
 26 November 2024
 
 
 Trustindex verifies that the original source of the review is Google. We have both our home and auto with Howes Insurance. Recently, we had a very challenging purchase of an auto and damage to our house. In both situations they were incredibly helpful and reassuring. Highly recommend the team and a special shout out to Traci.
  
 
      Posted on Google  
   
   Gregory Ladd 
 30 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The personalized service and breath of offerings really makes a difference!
  
 
      Posted on Google  
   
   Steve Neff 
 3 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The Howes team has been a valued services and support team. They are knowledgeable, proactive and we have a comprehensive umbrella policy for multiple properties, cars etc. Also a big shout out to our Account Manager Jennifer Drasser.
  
 
      Posted on Google  
   
   Jack 
 23 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. From the moment I placed a call to Greg Howes, I knew I was in good hands. He took the time to explain every detail of the half dozen properties and autos I wanted to insure and came in less than other quotes at a higher level of coverage! Jennifer continued the process with countless phone conversations and emails. She's knowledgeable, patient, helpful, empathetic, experienced and extremely affable. I can't say enough and am grateful to have found Howes Insurance Group. You will be too!
  
 
      Posted on Google  
   
   Sylvia Diaz 
 6 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. It's' a comfort for me to know that I have The Howe's Insurance Group behind me to help me navigate the complex business of insurance.

The Howe's Insurance Group is very responsive to my questions and needs. Together, we review, my family's insurance needs every year.