Agency website
About us
Specializing in Workplace benefits Across Massachusetts and Beyond.
I help customers make clearer, more confident decisions about Auto, Home, and Life insurance - especially through employer-sponsored insurance programs.
After 29 years in the insurance industry, I've learned something simple: Most people do not want more insurance jargon.
They want someone experienced, honest, and easy to reach. Before opening my own office in Hopkinton in 2012, I spent 15 years inside a high-volume MetLife call center environment selling insurance policies across all 50 states.
That experience gave me something you cannot learn from a script: tens of thousands of real conversations with real customers making real decisions about protecting their homes, cars, families, and financial lives.
Today, I primarily work with Farmers Insurance Group, helping customers access Auto, Home, and Life insurance options, including employer-sponsored group programs. These programs may offer meaningful advantages for eligible employees, including:
• Group-based discounts
• Payroll deduction options
• No down payment structures in many cases
• Convenient onboarding through employer benefit programs
• Access to Auto, Home, and Life coverage options
• Guidance from a licensed professional who understands Massachusetts insurance procedures I specialize in helping customers cut through the noise of automated systems and AI prmpts, call centers, phone trees, chat bots, language barriers, and rushed advice
My approach is straightforward: real conversations, practical guidance, and coverage decisions based on experience - not guesswork.
If you would like a second opinion on your Auto, Home, or Life insurance, send me your declarations page or book a quick policy review call. I'll help you understand where you stand, what options may be available through your employer, and what steps make sense next.
What our clients are saying
"I came to the Flanagan agency out of frustration that my current agent was difficult to communicate with and not helping me find the ideal policies for me in terms of price and coverage. I am thrilled I did! Excellent communication and saved me $700 off my "current best option" for insuring multiple vehicles. Cannot thank Flanagan enough!"
"I've known Kevin for a decade now, he is incredibly knowledgeable and takes time to explain everything clearly, which makes the process smooth and stress-free. His friendly attitude and responsiveness makes me feel truly supported throughout. Im grateful for Kevin's professionalism and dedicationits rare to find someone who genuinely puts their clients first."
"Last meeting was very productive. Reviwed homeowner policy and updated at considerable annual savings with better coverage"
"Great to work with a very professional gentleman. Kevin guided me to gain the best auto insurance policy with extreme efficiency and accuracy."
"Jackie was so great to me. She had my whole policy settled in the time I was on the phone with Progressive, at a great rate too. I appreciate her flexibility and timeliness."
"Angela's service has been stellar - she is extremely responsive, offers creative solutions, and is always willing to go the extra mile to ensure that my insurance concerns are satisfied."
"Jackie was amazing. She really took the time to make sure i understood everything, as it was my first time looking at car insurance. She got me the best price and was the kindest person in the world. Genuinely happy she is my agent."
"Just bought a new truck and was nervous about how much it was going to cost to get insurance. Jackie went above and beyond to find me the lowest quote possible and explained everything crystal clear. She literally made my entire day and even more excited about my new truck knowing it wont cost me an arm and a leg to insure. I have worked with a lot of different agents in the past and Jackie was the best by far! I am so happy to have her as my agent going forward and hope she is my agent for a long time! Thanks again Jackie!"
"I worked with Jacqueline Densmore, she came highly recommended and I must day she didnt disappoint! She has exceptional customer service and patience. I told her I was shopping around to find the lowest price and she did not pressure me. She answered every single question I had sometimes twice when I had difficulty understanding."
"Angela has been extremely helpful in finding me good automotive coverage. Thanks Angela."
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Personal Lines insurance professionals
Ask me about these types of insurance...
Having the right car insurance is so important, even more important is understanding all the ins and outs of your coverage to help protect you.
Request an automobile insurance quoteGet multiple quotes on your homeowners insurance with one phone call. Let an independent agent shop for you.
Request a homeowners insurance quoteOur independent insurance agents are here to help you find the best life insurance that will take care of those you leave behind.
Request a life insurance quoteAn annuity is an investment product issued by an insurance company that provides you with guaranteed periodic payments in return for your initial investment.
Request a annuities quoteAn independent insurance agent will walk you through top umbrella policy options to make sure you have the proper coverage to tackle above and beyond claims.
Request an umbrella insurance quoteWhy choose Flanagan Agency LLC
States we serve
- Connecticut
- Maine
- Massachusetts
- New Hampshire
- New York
- Rhode Island
- Virginia
Our insurance coverages
Personal insurance coverage
- ATV
- Automobile
- Boat
- Builders Risk / Construction
- Condo
- Flood
- Home
- Identity Fraud
- Landlord
- Mobile Home
- Motorcycle
- Other
- Personal Watercraft
- Pet
- RV / Motorhome
- Renters
- Snowmobile
- Travel Trailer
- Umbrella
- Vacant Land
Business insurance coverage
- Accident & Health
- Bonds
- Builders Risk
- Business Owners Package (BOP)
- Business Vehicle
- Contractors Equipment
- Cyber Liability
- Directors & Officers
- Employment Practices Liability
- Errors & Omissions
- General Liability
- Inland Marine
- Other
- Professional Liability
- Property
- Umbrella / Excess
- Workers' Compensation
Life & Annuities coverage
- Annuities
- Disability Income
- Life
Recommended insurance company partners
Other companies we work with:
Aetna, Ameritas, Assurity Life, Banner Life, Bristol West Insurance Company, Burns & Wilcox, CNA, Chubb, Farmers Insurance Company, Legal & General America, Lloyd's, Mass Property Insurance (MPIUA), MetLife Auto & Home, Neptune Flood, Next Insurance, Openly Insurance, Orchid Insurance, Orchid Insurance Company, RPS, SBLI, Safeco Insurance, SageSure Insurance, Senior Life Insurance Company, Steadily, Swyfft Insurance, TAPCO, The General, TruStage Insurance, US Assure, Vacant Express, Vault Insurance, XS BrokersFlanagan Agency LLC Team
Flanagan Agency LLC Reviews
Customer Reviews
I came to the Flanagan agency out of frustration that my current agent was difficult to communicate with and not helping me find the ideal policies for me in terms of price and coverage. I am thrilled I did! Excellent communication and saved me $700 off my "current best option" for insuring multiple vehicles. Cannot thank Flanagan enough!
I've known Kevin for a decade now, he is incredibly knowledgeable and takes time to explain everything clearly, which makes the process smooth and stress-free. His friendly attitude and responsiveness makes me feel truly supported throughout. Im grateful for Kevin's professionalism and dedicationits rare to find someone who genuinely puts their clients first.
Last meeting was very productive. Reviwed homeowner policy and updated at considerable annual savings with better coverage
Great to work with a very professional gentleman. Kevin guided me to gain the best auto insurance policy with extreme efficiency and accuracy.
Jackie was so great to me. She had my whole policy settled in the time I was on the phone with Progressive, at a great rate too. I appreciate her flexibility and timeliness.
Angela's service has been stellar - she is extremely responsive, offers creative solutions, and is always willing to go the extra mile to ensure that my insurance concerns are satisfied.
Jackie was amazing. She really took the time to make sure i understood everything, as it was my first time looking at car insurance. She got me the best price and was the kindest person in the world. Genuinely happy she is my agent.
Just bought a new truck and was nervous about how much it was going to cost to get insurance. Jackie went above and beyond to find me the lowest quote possible and explained everything crystal clear. She literally made my entire day and even more excited about my new truck knowing it wont cost me an arm and a leg to insure. I have worked with a lot of different agents in the past and Jackie was the best by far! I am so happy to have her as my agent going forward and hope she is my agent for a long time! Thanks again Jackie!
I worked with Jacqueline Densmore, she came highly recommended and I must day she didnt disappoint! She has exceptional customer service and patience. I told her I was shopping around to find the lowest price and she did not pressure me. She answered every single question I had sometimes twice when I had difficulty understanding.
Angela has been extremely helpful in finding me good automotive coverage. Thanks Angela.
We prioritize honest feedback from our clients to assist future customers in making well-informed decisions. Our review section showcases authentic experiences from real customers. When a less-than-positive review is submitted, we share it with both the agent and the reviewer to foster collaboration and improvement based on constructive feedback. We also moderate reviews to remove inappropriate content or spam, upholding a high standard of trust and transparency.
