Selling Here to Buy There: What Your Equity Actually Has to Cover
If you are selling an Ontario home to move to the U.S., the sale usually has to fund four separate things: an investment property, the business built around it, a home to live in, and a cushion to live on while it all gets going. The people who make this work are not spending their last dollar to do it.
I have had more conversations about this in the past year than in the previous ten combined. People are not asking me what their house is worth so they can move to Aurora. They are asking so they can work out whether they can afford to leave.
So I had Lauren Cohen back on the podcast. She is a lawyer licensed in Canada and the U.S., a Florida realtor, and a fourth generation Torontonian who grew up in Thornhill and moved to South Florida 25 years ago. She has spent the years since helping Canadians do the same thing.
I want to be clear about my lane here. The part I know is what your Ontario house is worth and how to sell it properly. Everything downstream of that is for a cross border lawyer and accountant. But the sale is the first domino, and most people get the sequence wrong.
What does the home sale actually have to pay for?
This was the part that reframed it for me. People think of it as one transaction: sell the house here, buy a house there. It is not.
“Oftentimes, I’m working with clients that have enough equity in their home to both buy the real estate, develop the business, and buy the real estate investments for developing the business, and buy a home for their own personal use, and still have leftover proceeds from the sale of their home.”
Read that again slowly, because there are four separate line items in it.
Lauren is blunt about who should not do this:
“I’m not working with somebody that’s using their last $150,000 to make the move, because they shouldn’t move, because they don’t have enough support in case… Listen, not every business works. Not every plan works. Maybe your kids will hate it.”
That is the most useful sentence in the whole episode, and it is a lawyer talking herself out of business. If the move consumes everything you have, the answer is not yet.
Lauren’s whole approach runs in that order. “You don’t pick the visa and then find the business. You pick the strategy and then fit the visa in.” Which means the useful early question is not which visa you qualify for. It is what you are actually trying to build, and what your equity can support.
The healthcare question, which everybody asks first
I did not even have to raise it. I started the question and she finished it.
“Healthcare? Yeah, but they don’t have free healthcare and we do. Do you think it’s really free?”
Her argument is that ours is free in quotation marks, because it comes out of taxes, and that comparing a U.S. insurance premium against zero is the wrong comparison. Compare it against the tax you already pay here.
“I pay under $700 a month for me, but I have amazing coverage, dental and vision included. Now, that is not a lot of money to come out of my pre-tax dollars, so I don’t pay tax on that.”
Then the caveat, which matters more than the number:
“Again, if you have preexisting conditions, it’s a little more challenging.”
That figure is what one healthy person pays for her own coverage in Florida. Age, health history, state and family size all move it, and they can move it a lot. Treat it as proof that the number is knowable, not as your number. This is a question for a licensed insurance professional where you are going.
The currency question, which everybody asks second
“So the first most common question is healthcare. And the second most common question is, oh my God, what about the exchange rate?”
Her answer is a story. She sold her place at King and Bathurst and moved the money down to buy her house in Florida. I guessed she got hurt on it. She did.
“What were we at, 60 cents? Exactly. It was the worst.”
Around 60 cents, and she did it anyway, more than twenty years ago. Her point is not that the rate does not matter. It is that it is one input and it stops mattering the moment the transaction is done.
“And it’s done. So now, when I come here, home to Toronto, I’m still home. Everything’s on sale. If I spend $500, it’s $350.”
One practical note she raised: on a move of this size the spread you pay to convert is real money, and she works with currency exchange partners rather than moving it through a retail bank. She puts the difference in the tens of thousands on a large transfer. Worth pricing before you move a lump sum, whoever you use.
Waiting for the perfect time is the actual risk
The part of this conversation I keep thinking about had nothing to do with money.
“So I think the problem with a lot of Canadians is they are small-c conservative. And they think they’re very risk-averse. But instead of being risk-averse, take that first step.”
“You can’t just wait until the perfect time because there’s no perfect time for anything.”
I told her about someone in my own family, in her seventies, who has decided she will not travel to the States while the current president is in office. That is four years. In your seventies. I could not make that math work.
Lauren’s business lived through the same instinct on a larger scale. From February, when the tariffs were announced, through to October, her Canadian business was, in her word, dead. Three clients backed out. Then the weather turned here and the phone started ringing again, because people can drive to Florida and they cannot drive to the Dominican.
Find out what your house is worth today. Every other number depends on it and most people are working off a figure from 2022.
Talk to a cross border lawyer and accountant before you list, not after. How you hold U.S. property and what route you are on are easier to structure before a sale.
Build the four bucket budget and see whether the fourth bucket has anything in it. If it does not, you have your answer for now.
Nothing says you have to go immediately. In Lauren’s words, you do not have to move day one, and you do not have to move day 366.
Where I actually come into this
I am not going to pretend to advise anyone on U.S. immigration or tax. I sell houses in Toronto and York Region.
But every one of these plans starts with the same question, and it is mine: what is the Ontario house worth, and what does it take to get full value for it in this market? That number is the foundation everything else sits on, and getting it wrong by a hundred thousand dollars changes whether the plan works at all.
It is also worth saying plainly that most of the people asking me this do not end up leaving. They want to know the number so they can decide. That is a completely legitimate reason to find out.
Frequently Asked Questions About Selling in Canada to Move to the U.S.
How much equity do I need to move from Canada to the U.S.?
Is healthcare in the U.S. really unaffordable for Canadians?
Should I wait for a better Canadian dollar before moving?
What should I do first if I am thinking about selling and moving south?
Do I have to move right away once I start the process?
Related Reading
- 3 Things to Know When Selling Your Home, the starting point for the number everything else depends on.
- Should I Buy or Sell First?, which gets more complicated when the purchase is in another country.
- Home Seller Checklist, worth working through early if a move is a year or more out.
- Canada’s Economic Crisis and Toronto Real Estate, for the backdrop these conversations are happening against.
Watch the Full Episode
This is from my conversation with Lauren Cohen on Supply and Demand. We also get into the co-living investment model she uses, why a real estate licence takes 63 hours in Florida and closer to a year here, and what I have been seeing buyers’ lawyers do on closing day. Listen on Apple Podcasts or Spotify.
You can find Lauren Cohen at Investing Across Borders.
If you want to know what your house would actually sell for in this market, whether you are moving to Florida or to Newmarket, I am happy to give you a straight number with no pressure attached to it.
Written by Adam Nadler, a licensed REALTOR serving Toronto and York Region with RE/MAX Your Community Realty, Brokerage. Nothing here is legal, immigration, tax, insurance or investment advice, and no solicitor client relationship is created by reading it. Figures quoted are those of the guest, reflect her own circumstances at the time of recording, and will differ for you. Immigration programs, tax treatment, insurance pricing and exchange rates change frequently. Always retain qualified professionals in both countries before acting.