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Best Health Insurance Agencies in Boston, MA

Our Recommended Top 3

We did the research for you!

  • Licensing
  • User Reviews
  • Mystery Shopping Calls

Our goal is to connect people with the best local professionals. We scored Boston Health Insurance Agencies on more than 25 variables across five categories, and analyzed the results to give you a hand-picked list of the best.



3Top Picks

Learn about our selection process.


featured provider = Featured Provider

30 Federal Street, Salem, MA 01970 Rating

Review Sources

5.0 (1)

Why choose this provider?

Woodward Insurance is an independent agency serving the Boston community. It offers a wide range of employee benefits insurance, including health, dental, vision, disability, and Medicare plans. Life insurance and wellness programs are also available. Moreover, the agency serves as a resource for businesses and their employees by providing on-site enrollment and presentations, customized employee benefits statements, and one-on-one employee meetings and benefits reviews. Its founder, Brady Woodward, established the business with the goal of providing personalized services for small and medium-sized businesses.

  • Individual Plans
  • Life Insurance

4 Copley Place, Boston, MA 02116 Rating

Review Sources

5.0 (1)

Why choose this provider?

KD Hicks Insurance Agency, Inc. is an independent agency serving residents of the Boston area. Individual health insurance is available with health maintenance organizations, point-of-service, preferred provider organizations, fee-for-service options. Group health and dental insurance are also available. Other products include personal insurance for homeowners, renters, auto, and motorcycle as well as business insurance for worker's compensation, general liability, commercial auto, and bonds. As an independent agency, it represents multiple companies for clients to have options to choose from.

  • Individual Plans
  • Life Insurance

135 Wood Road, Braintree, MA 02184 Rating

Review Sources

4.0 (23)

Why choose this provider?

HSA Insurance has been offering insurance solutions to individuals and businesses in Boston and its neighboring areas for nearly 50 years. It offers health and ancillary insurance products to self-employed individuals and small businesses, which include medical, dental, and disability coverage. In addition, it caters to clients who need life, property, and casualty insurance. HSA Insurance also partners with multiple carriers, such as Tufts Health Plan and Delta Dental, enabling its clients to choose from more than 200 medical plans.

  • Individual Plans
  • Group Plans
  • Life Insurance

Compare our Top Health Insurance Agencies

NameExpertise RatingAddressPromotionsLearn more
Woodward Insurance
30 Federal Street, Salem, MA 01970
KD Hicks Insurance Agency, Inc.
4 Copley Place, Boston, MA 02116
HSA Insurance
135 Wood Road, Braintree, MA 02184


  • Introduction

    If you're looking for health insurance for yourself or your family, an agent can help you save time, understand your options, and manage your costs. Insurance agents must be licensed in the state where they operate. They can provide information about on- and off-exchange plans to help you weigh all of your options, and they can see if you qualify for tax credits that can lower your monthly premiums. There's no cost to work with an agent, and they can help you save quite a bit by recommending the best plan for your needs. Here's what you should know before you get started.

  • Is health insurance mandatory for residents of Boston?

    Yes. Massachusetts enforces an "individual mandate" requiring residents aged 18 and up in Boston to maintain health insurance. This insurance should adhere to "minimum creditable coverage" standards, encompassing prescription coverage, pre-deductible doctor visits, specific deductible limits, and out-of-pocket maximums. It shouldn't limit yearly benefits or daily hospital expenses. If religious beliefs prevent insurance, a sworn statement can be included with the state tax return.

  • What options do Boston residents have if they can't afford insurance plans via the Connector?

    If Bostonians don't have insurance access through work, a spouse, or parent and find Connector plans unaffordable, they might qualify for public health insurance programs. Eligibility hinges on income and specific criteria. Public programs, including Medicare and MassHealth, offer alternatives for those needing coverage without the financial means for standard plans. It's essential to explore these avenues if facing financial constraints.

  • How do Bostonians determine eligibility for MassHealth?

    Boston residents can access MassHealth, a free or low-cost state health insurance, based on income levels and needs. In 2023, individual income limits are set at various Federal Poverty Levels, from around $14,000 to $27,000. The threshold rises with more family members, though those with disabilities aren't restricted by income. All income sources, such as wages and pensions, count towards these limits. Specific requirements differ based on the Medicaid program type, like Nursing Home Medicaid.

  • What should Bostonians know about waiting periods in health insurance plans?

    A waiting period in Boston health insurance plans is a predetermined time after enrollment during which the insurer won't cover health services. Ideally, residents should seek plans with no waiting period for immediate coverage. In Massachusetts, the longest permissible waiting period for any plan is four months. It's crucial to be aware of these durations when choosing health coverage to ensure timely access to care.

  • Can an ex-spouse in Boston remove their former partner from their health insurance unilaterally?

    Typically, if a Boston judge directs an individual to maintain their ex-spouse on their fully insured health plan, both the insurer and employer must comply, given the health plan remains unchanged. However, remarriage might affect this arrangement. In such cases, consulting an attorney is advisable to ascertain the judgment's continued applicability and to explore potential alternative health coverage options.

  • How can you find affordable health insurance? 

    Affordable insurance is available through employers, Medicare, Medicaid, and the federal Health Insurance Marketplace, which offers subsidies in the form of tax credits. You can also purchase coverage through private insurance companies and independent agents. Nearly half of all Americans have employer-sponsored health insurance, and about 10% of the population is uninsured.