Most of what I know about a beneficiary living in estate property in Ontario, I learned from parents, sitting across from me in my office, who assured me things would work out.

The setup can differ but the result is the same. An adult child has been in the house for years, paying little to nothing, and everyone in the family understands they’ll stay on for a while after the parents are gone.

When I ask whether they’d like to put that in the will, I get a blank stare. Most of them have never considered the possibility.

Last week the Ontario Superior Court showed exactly what that costs.

What the Court Decided About a Beneficiary Living in Estate Property

On August 26, 2026, the court released its decision in The Estate of Sean Craddock et al. v. Daviau.

A residual beneficiary was living in a home owned by the estate. When the estate trustee moved to sell it, the resident beneficiary went to court to stop the sale, on the basis that she had a right to stay.

The court disagreed. Being a residual beneficiary entitles you to a share of whatever is left once the estate is settled. It does not give you an interest in any particular thing the estate happens to own along the way.

The will did not leave her the house. It did not give her a life interest, a trust interest, or a right of occupation. Without that, there was no legal basis for her to remain.

The court also declined to consider evidence about what the deceased had supposedly wanted. That is a common outcome in Ontario, though it always depends on the circumstances. Where a will is clear on its face, you don’t get to top it up with what someone recalls being said at a kitchen table while everyone was still alive.

The “squatter” was ordered to leave within sixty days and to pay occupation rent and carrying costs for the time she stayed on.

Why “Everyone Knows” Is Not an Estate Plan

The trouble with a family understanding is that it works beautifully right up until the person who created it dies. After that it becomes a memory, and three people remember things three different ways.

Executors don’t administer an estate based on the mood in the room. They administer it based on the will. If the will says nothing, the executor’s job is to collect the assets, sell what has to be sold, and distribute the money.

That includes the house your grown child is currently residing in.

What Your Will Should Actually Say About Someone Staying in Your Home

None of that was inevitable. Every bit of it could have been written into the will.

If you want someone to be able to stay in your home, say so, and then answer the boring questions that follow immediately. For how long? Until they turn a certain age, until they remarry, until a fixed number of years runs out, or for the rest of their life?

Who pays the property taxes, the insurance, the utilities, and the roof when it finally goes? A right to live somewhere rent free is not the same as a right to live somewhere for free, and families tend to discover that difference in year two.

Can your executor sell the property anyway if the estate needs the cash, and what happens to the occupant if she does? What if that person simply refuses to leave when the time is up?

None of this is difficult to draft. It’s only difficult to talk about, which is a different problem, and one we spend more time on than the drafting. It belongs in the same conversation as your wills and powers of attorney, not in a separate one nobody schedules.

What to Do if You Are the Executor

If you’re administering an estate where a beneficiary is living in the property, read the will before you read the family group chat. Our Executor’s Handbook walks through the rest of the job in order.

If the will gives that person a right to be there, you have to honour it. If it doesn’t, your duty runs to the estate and to the other beneficiaries, and that duty may point toward selling.

It is an uncomfortable place to stand, and there is usually a reason the person is still living there. Get advice on administering the estate before the conversation becomes an application.

The Question Worth Asking Now

If you’re a financial planner or an advisor, you have faced this as often as we have. Ask your client whether anyone is expected to keep living in their home after they die.

Then push for the harder conversation, and get the answer into the estate plan alongside the lawyer, rather than leaving it as something the family assumes.

A surprising number will recognize the problem. Almost none of them will have planned for it in writing.

Every one of those parents in my office told me it would all work out. It worked out for the Craddock estate too, eventually, in a courtroom.

If someone is expected to stay in your home after you’re gone, talk to us and we’ll put it in writing.