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Your Trusted Partner for Comprehensive Insurance Solutions
Roger Keith & Sons Insurance Agency Insurance Agency has been a cornerstone of the Massachusetts insurance industry since 1869. Our agency combines over 150 years of experience with a personalized approach, working directly with clients to understand their unique needs and provide tailored insurance solutions. We maintain direct relationships with more than 40 insurance carriers, allowing us to offer competitive rates and comprehensive coverage options.

Our team of 35 experienced agents serves individuals and businesses across five office locations, prioritizing both informed decision-making and continuous client support. Through strategic affiliations like our Assuralliance Membership, we combine national-level resources with localized service delivery to maintain our position as a trusted insurance advisor in the region.
Services
Business Insurance Personal Insurance Commercial Trucking Insurance Medical Malpractice Insurance Nonprofit Insurance Homeowners Insurance Commercial Property Insurance Workers Compensation Auto Insurance Umbrella Policies
Highlights and features
  • 150+ years of continuous service to Massachusetts communities
  • Access to 40+ insurance carrier partners for competitive rates
  • Personalized service through 35 experienced local insurance professionals
  • Five convenient office locations across southeastern Massachusetts
  • Specialized expertise in medical malpractice, commercial trucking, and nonprofit insurance
Associations and certifications
  • Assuralliance
What people say
Great service Amazing agent Best rates Timely manner Super responsive
Services
Business Insurance
Our business insurance solutions protect Massachusetts companies of all sizes with customizable commercial property, liability, and specialized coverage options. We offer industry-specific policies for contractors, healthcare providers, nonprofits, and transportation companies. With access to multiple carriers, our experienced agents help businesses secure comprehensive protection that aligns with their risk management needs while maintaining cost-effectiveness.
Personal Insurance
We provide tailored personal insurance products including homeowners, auto, umbrella policies, and specialty coverage for high-value assets. Our agents work closely with Massachusetts residents to create customized protection plans that evolve with life changes. From standard policies to unique insurance needs, we deliver personalized service through our local office network.
Medical Malpractice Insurance
Specialized medical professional liability coverage for Massachusetts healthcare providers, including physicians, nurses, and medical facilities. Our dedicated team understands the complex risk landscape facing healthcare professionals and offers access to top-tier carriers with expertise in medical liability insurance.
Commercial Trucking Insurance
Comprehensive insurance solutions for trucking companies and owner-operators operating in Massachusetts and beyond. Our coverage options include liability protection, cargo insurance, and physical damage coverage tailored to the transportation industry's unique requirements. We serve both small fleets and large commercial trucking operations.
Nonprofit Insurance
Customized insurance programs designed specifically for Massachusetts nonprofit organizations, including general liability, directors & officers coverage, and property insurance. Our agents understand the unique risk exposures faced by charitable organizations and work to provide cost-effective protection that supports their mission continuity.
People
Donovan Dunn
President
Insurance industry veteran with 20+ years of experience, leading the agency since 2001. Holds Certified Insurance Counselor and Accredited Advisor in Insurance designations. Specializes in life, benefits, and financial services while maintaining active involvement in local healthcare foundations.
Sherry Meadows
Vice President/Account Executive
Commercial lines specialist with 30+ years of experience creating customized insurance solutions for Massachusetts businesses. Active in industry associations and previously served on Liberty Mutual's advisory board. Focuses on innovative risk management strategies for business clients.
Anna Bailey
Chief Operating Officer
Insurance professional with 35+ years of experience, holding multiple industry certifications including Certified Risk Manager. Specializes in medical malpractice and financial institutions insurance. Provides strategic leadership in risk management solutions and captive insurance programs.
Diane Resendes
Account Manager - Personal Lines
Recognized for exceptional client service in personal insurance, consistently exceeding client expectations. Maintains active CISR certification and demonstrates expertise in Massachusetts personal insurance markets while delivering personalized coverage solutions to policyholders.
Linda St. Don
Manager - Personal Lines
Experienced personal lines manager with LIA and CISR designations, providing insurance solutions to Massachusetts residents. Combines technical expertise with personalized service to help clients navigate their insurance needs across multiple product lines.
Questions
What types of insurance do you offer?
We provide personal insurance (home, auto, umbrella) and commercial insurance (property, liability, trucking, malpractice) for individuals and businesses across Massachusetts.
How can I get a competitive insurance quote?
Contact our agents at any of our five Massachusetts locations to receive customized quotes from multiple carriers, ensuring optimal coverage and pricing.
Do you offer specialized business insurance?
Yes, we specialize in niche commercial coverage including medical malpractice, nonprofit insurance, and commercial trucking policies tailored to specific industry needs.
What payment options are available?
We offer flexible payment plans through our carrier partners - contact your local agent for specific payment arrangements and financing options.
How do I file an insurance claim?
Report claims through our website or contact your assigned agent directly for immediate assistance with the claims submission process.
Are your agents licensed professionals?
All our insurance professionals maintain active state licenses and industry certifications, with many holding designations like Certified Insurance Counselor (CIC).