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 assumed that everything would work itself 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 seemingly 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 look. 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, Justice Jensen released the decision in The Estate of Sean Craddock et al. v. Daviau.

Sean Craddock died in 2022, leaving a house in Ottawa that was the main asset of his estate. The will did not give the house to anyone. It fell into the residue, to be divided among his son and two stepsons.

His son Jacob moved in after the death, with the estate trustee’s permission, on a temporary basis while the estate was administered. In 2024 the beneficiaries and the trustee reached an agreement. Everyone got a final chance to buy the house, and if nobody did, the occupants would leave by August 1 and the house would be listed.

Nobody bought it. One occupant moved out as agreed. Jacob took his share of the interim distribution and stayed.

Almost two years later the estate went to court, and Jacob went to court to stop the sale.

He lost. 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 him the house. It did not give him a life interest, a trust interest, or a right of occupation. Without that, there was no legal basis for him to remain.

Jacob argued that his father had said he wanted the house kept in the family. The court would not hear it. Where a will is clear on its face, you don’t get to top it up with what someone recalls being said while everyone was still alive.

The judge was sympathetic to his circumstances and said so more than once. It made no difference to the outcome.

He was ordered to leave within sixty days. He was ordered to pay occupation rent of $2,900 a month running back to August 2024, roughly $78,000 by the time he goes. He was ordered to pay $8,275.32 in utilities. And he was ordered to pay $16,000 in costs.

Call it $102,000, over a house nobody left him.

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 Say About a Beneficiary Living in Estate Property

None of that was inevitable. As the judge put it, had Sean intended to grant his son a life interest or a right of occupation, he could have done so. He did not.

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 he 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.

Worth noting what the trustee in Craddock actually did, because it is why he won. He let Jacob stay. He got an appraisal. He gave the beneficiaries a chance to buy. He waited almost two years past the deadline before going to court. The judge found no bad faith anywhere in that, and the costs award followed.

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 say yes. 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, for about $102,000.

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