SELLING BEFORE BUYING: WHY ONE COUPLE CHOSE TO LIST FIRST (AND WHAT YOU CAN LEARN)
by John Merrill & Larry Osmond
August 14, 2025
It’s a question that many homeowners wrestle with, especially when timing, inventory, and finances can all collide. After extensive discussions with various professionals, including their Realtor, financial planner, and others, they weighed the options and chose to sell their existing home first. While it wasn’t without stress, it ultimately proved to be the right move for them. Here’s how they made their decision, and what you should know about both approaches.
Why They Chose to Sell First
Emma and Daniel’s reasoning came down to minimizing risk, financial security, and avoiding overlap. They couldn’t afford to carry two properties at the same time along with all the costs that go with each (mortgage payments, insurance, property taxes, utilities, and maintenance). In fact, for them, that wouldn’t have even been an option as the mortgage on the home they eventually purchased was pre-approved conditional on selling their existing home. So, if they bought first and then their existing home didn’t sell before the closing date on their new home, they almost certainly wouldn’t have been able to close on the new home. This would have put them in breach of their purchase agreement, which could have opened them up
to extremely costly litigation.
More often than not, buyer breach cases in the courts are settled by way of a simple summary judgement, which means a buyer in breach of their contract could quickly be facing a significant judgement in favour of the seller. The buyer in breach would likely be on the hook for any difference in sale price if the seller had to take less money when they resold the property, all carrying costs until the sellers could successfully close on the property to a new buyer, all legal costs, plus court fees and interest. It’s not uncommon to see judgements of hundreds of thousands of dollars against buyers in breach. Needless to say, buyers should not risk this outcome and, by any means possible, find a way to close if not closing becomes a possibility.
Even in a hypothetical scenario where Emma and Daniel bought first and managed to get a firm deal in place on their existing home, but the closing dates didn’t align creating an overlap (carrying two properties for some period of time, say a couple weeks), this would mean added expenses for bridge financing. Sometimes, bridging makes sense as it can allow time for renovations and make a move less stressful by not having to move fully from one house to another on the same day. But, in this case, Emma and Daniel were only looking at homes that were mostly turn-key and without the need for renovations, so they felt bridging costs were an unnecessary extra expense.
By selling first, they knew exactly how much equity they’d have to put toward their next purchase and would avoid the crushing stress they’d surely experience if their current house sat on the market longer than expected, sold for less than anticipated, or didn’t sell at all.
Selling First: Pros, Cons, and Risks
✅ Pros
⚠️ Cons
�� Risks
Buying First: Pros, Cons, and Risks
If Emma and Daniel had decided to buy first, here’s what they might have faced instead:
✅ Pros
⚠️ Cons
�� Risks
The Bottom Line
For Emma and Daniel, selling first gave them peace of mind and a clear budget and that outweighed the risks that can come with buying first.
The right choice for you depends on your financial resources, flexibility, tolerance for uncertainty, and local market conditions.
In either case, work with a knowledgeable real estate professional who can help guide you through decisions like these. They can also connect you with other professionals such as financial planners, mortgage brokers, and real estate lawyers who can also provide valuable guidance. You’ll then be better prepared to make the move that’s right for you.
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