Health Insurance for Real Estate Teams and Brokerages
If you run a team or a brokerage, you’ve probably had this conversation: a good agent is thinking about leaving, and somewhere in it they mention health insurance. You’d like to help. The structure makes it complicated.
Why This Is Harder Than It Looks
Traditional group health insurance is built for employees. Your agents are independent contractors, and that classification is load-bearing — it’s why you don’t withhold payroll taxes and why the commission structure works the way it does.
Offering employee-style benefits to contractors can create classification risk. It’s not that you can’t help; it’s that the obvious path isn’t available, and improvising here has consequences beyond the insurance itself.
Talk to an employment attorney or CPA before implementing anything. Classification questions are their territory, and the cost of getting it wrong exceeds the cost of the advice.
What Teams Actually Do
Bring in an advisor for the team. The lowest-friction option. You arrange for a licensed advisor to walk your agents through their individual options — group education, individual policies. No classification exposure, no cost to the brokerage, and it addresses the real problem, which is usually that agents don’t know what’s available rather than that they can’t afford anything.
Cover W-2 staff properly. Most brokerages have some genuine employees — admin, transaction coordinators, marketing. Those people can be covered through a conventional small group plan, and if you have enough of them, that’s worth doing on its own merits.
Look at ICHRA. Individual Coverage Health Reimbursement Arrangements let an employer reimburse employees tax-free for individual coverage. Whether and how this can extend to a contractor workforce is exactly the question to put to your CPA — the answer depends on your specific structure.
Negotiate association or group-rate access. Some professional associations offer members access to coverage options. Availability varies considerably by state and by association, so verify what your agents can actually access rather than assuming.
Why It’s Worth Bothering
Recruiting and retention are the whole game in this business, and health insurance is one of the few remaining differentiators when everyone’s commission split looks similar.
That became more true in 2026. The ACA’s enhanced premium tax credits expired at the end of 2025, and agents buying their own coverage saw real increases. A brokerage that helps its agents solve this — even just by bringing in someone who knows the landscape — is offering something concrete at a moment when it’s newly painful.
It also costs you very little. An advisor session for your team is free to the brokerage.
A Reasonable First Step
Ask your agents what they’re currently doing for coverage. The answers usually reveal that several are uninsured, several are overpaying, and most haven’t looked at it in years.
I’m licensed in 31 states and work with real estate professionals regularly. If you’d like me to run a session for your team — no cost, no obligation, and agents can follow up individually or not — book a consultation and we’ll set it up.
General information, not legal, tax, or employment advice. Worker classification and benefit arrangements should be reviewed with qualified counsel.
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