Individual & Family Health Insurance in Massachusetts

If you’re under 65 and don’t get health insurance through an employer, you have options — but the Massachusetts marketplace can be confusing. Wilson Advisory Group helps individuals, families, self-employed professionals, and early retirees compare plans and pick coverage that fits.

We’re licensed as an independent broker, which means we work for you, not for a single insurance company. There’s no cost to use our services — carriers pay us a standard commission whether you enroll on your own or through us.

Who We Help

Massachusetts residents shopping the Health Connector. Self-employed professionals and small business owners. Families needing dependent coverage. Early retirees under 65 bridging the gap to Medicare. People losing employer coverage due to a job change or other qualifying event.

Plan Types

The Massachusetts Health Connector offers several plan tiers — Bronze, Silver, Gold, and Platinum. The trade-off is straightforward: higher metal tier means higher monthly premium but lower out-of-pocket costs when you use care. Picking the right tier depends on how often you expect to need care and your appetite for risk.

We also work with off-exchange plans — coverage you can buy directly from carriers outside the Connector. Off-exchange plans can sometimes offer broader networks or different price points, especially for households that don’t qualify for premium subsidies.

Subsidies and Cost-Sharing

Many Massachusetts residents qualify for help paying for coverage. Federal premium tax credits and state-level ConnectorCare subsidies can substantially reduce monthly costs, but eligibility depends on household size and income. Part of what we do is help you understand whether you qualify and which plans pair best with your subsidy.

Special Enrollment Periods

Open Enrollment for individual and family health insurance runs each fall. Outside that window, you can usually only enroll if you have a qualifying life event — losing job-based coverage, moving, marriage, divorce, having a child, and so on. We’ll walk you through whether you qualify and what timeline to plan around.

Free Consultation

Call 781-357-7573 or book an appointment online for a free conversation about your health insurance options.