SELLING BEFORE BUYING: WHY ONE COUPLE CHOSE TO LIST FIRST (AND WHAT YOU CAN LEARN)


When Emma and Daniel decided it was time to upgrade from their starter home and move into their “forever” home, they were faced with a big decision: Should they buy their new home first, or sell their current one first?

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

  • Financial Clarity – You know your exact budget before making an offer on your next home.
  • No Double Mortgages – Avoids the risk of paying for two homes at the same time.
  • Helps Ensure You Can Close – If you don’t qualify to carry two mortgages, selling first helps ensure you don’t face financial ruin.
  • Stronger Negotiating Position – With cash in hand or firm financing, your offers can be more attractive to sellers.


Cons

  • Temporary Housing May Be Needed – If you don’t find your ideal new home right away, you may need to rent or stay with family for some period.
  • Multiple Moves – You might have to move twice; once into temporary accommodation, then again into your new home.
  • Market Risk – Prices could rise in between selling your old home and buying your new one (though, the opposite could happen too, which would be a positive).

 

Risks

  • Limited Inventory – If there’s little available that suits your needs, you may feel
    pressure to settle for something less than ideal.
  • Lifestyle Disruption – Packing, storing belongings, and living in a transitional space can be stressful.



Buying First: Pros, Cons, and Risks


If Emma and Daniel had decided to buy first, here’s what they might have faced instead:


Pros

  • Smooth Transition – Move directly from your old home to your new one without temporary stops.
  • More Time to Shop – You can search for the perfect home without feeling as rushed.
  • Market Advantage – If prices are climbing, locking in your new home early can save money.


Cons

  • Two Mortgages – Assuming you qualify for two mortgages, you may need to carry the cost of both homes until your old one sells.
  • Bridge Financing Costs – Temporary loans to cover the overlap between two houses can add up.
  • Added Pressure to Sell – If your home takes longer to sell, you might be tempted to accept a lower offer.


Risks

  • Overestimating Sale Price – If your current home sells for less than expected, you could face financial strain.
  • Unexpected Delays – A slow sale could result in additional expenses that eat into your savings or force budget cuts elsewhere.
  • Inability to Close – If the existing home isn’t sold by closing day on the new home, not closing on the new home would then create the potential for litigation resulting in potential financial catastrophe.


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.


  • If you prioritize security and clarity, selling first may be best.
  • If you value convenience, finding your perfect match, and have the financial resources to potentially carry two properties at the same time, buying first could be the way to go.


In either case, work with a knowledgeable real estate professionals, like the Giles Team. We can help guide you through these decisions and 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 and informed to make the move that’s right for you.


GET IN TOUCH


As your trusted resource for all things real estate, we would be more than happy to provide you with additional insight on how to best prepare for buying or selling real estate. If you have any questions about the market, please reach out anytime. Want a better real estate experience? Call the Giles Team, we are always happy to help. 


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We look forward to connecting

DK and Amanda


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March 27, 2026
What to Expect in the Spring 2026 Real Estate Market in Southern Ontario Spring is traditionally the busiest season in real estate, and many buyers and sellers are wondering what the 2026 spring market will bring across Southern Ontario. After a period of market correction and shifting economic conditions, this year’s spring market is shaping up to be more strategic and opportunity-driven than the frenzied markets we saw during the pandemic years. Here’s what buyers and sellers should expect this spring. A More Balanced Market That May Tilt in Favour of Buyers The Southern Ontario housing market spent much of the past two to three years adjusting after the pandemic boom. Prices have come well off the peak in early 2022 with stabilization in many areas, but there’s still the possibility of further downward price pressure as spring inventory comes online. The market has shifted away from extreme seller dominance toward more balanced conditions while conditions in some communities are favouring buyers. Today’s market environment gives buyers more time to make decisions while still allowing sellers to achieve strong results if their homes are priced correctly and well presented. What this means: Buyers have more negotiating power Sellers must focus on realistic pricing and strong presentation Overpriced homes will sit longer on the market Well-priced properties can still attract strong interest, but the days of dozens of unconditional offers have largely passed. More Listings Are Expected to Hit the Market Spring always brings a surge of new listings, and 2026 is expected to follow that pattern. Some homeowners who delayed selling during uncertain market conditions may finally list their homes this spring, which is likely to increase inventory across many Southern Ontario markets. However, as many buyers take a cautious approach to their next steps factoring in a variety of concerns including tariffs, interest rates, inflation, global conflicts, and more, it’s possible that new inventory outpaces demand from buyers. In this scenario, we would expect to see softening prices and longer days on market. For buyers, this means: More choice and variety Less pressure to rush decisions Opportunities to negotiate on price or conditions For sellers, increased inventory means that standing out in the market will be crucial and realistic expectations are an absolute must. Interest Rates – The Ever-Present Concern Interest rates remain one of the biggest factors influencing housing demand. Many economists went into 2026 expecting the Bank of Canada to keep its key interest rate relatively stable this year provided inflation stays within target ranges. However, rising oil prices over the last couple weeks are already having an impact on the bond market, which have resulted in slight increases to fixed mortgage rates. If oil prices and the price at the gas pump remain higher, inflation could start increasing again, which would increase the likelihood of a higher overnight lending rate from the Bank of Canada. This would translate to higher interest rates on variable rate mortgages. But, should interest rates remain stable, buyer confidence could improve after the last couple tumultuous years, resulting in a gradual return of buyers. Given improved pricing and less competition, opportunities are certainly out there for buyers. The key for many buyers, though, is feeling comfortable with the interest rate environment. Lower Prices Than the Pandemic Years Rather than dramatic price increases or drops, most forecasts going into 2026 had suggested modest price improvement in 2026. The underlying assumption had been that we would see more stable economic conditions this year, particularly around interest rates. The conflict in Iran, though, may alter that expectation if rising oil prices result in higher inflation leading to higher interest rates. While that isn’t necessarily a certainty, it’s likely we won’t see much in the way of price gains. Instead, we may simply see a degree of balance or even further price decreases in areas where high inventory forces sellers to be more competitive in their pricing. In other words: There is the potential that prices could continue to soften A stable market would likely be the optimal outcome for 2026, and expectations of price growth should be muted Opportunities for Buyers Despite what may still feel like challenging times, the current market is creating more opportunities for buyers, especially first-time buyers. With greatly improved pricing, this may be the best opportunity in several years. Southern Ontario entered 2026 with improved affordability and lower pricing, creating a window of opportunity for strategic buyers. That said, desirable homes – especially those that are well presented, offer ideal locations, and in popular price ranges – can still sell quickly. Compared with the peak pandemic market: Prices are more realistic and notably lower over the last three years Inventory is higher providing much more choice Competition with other buyers is considerably lower Sellers Need a Strategic Approach While sellers can still achieve excellent results, success in today’s market requires strategy. Key factors for selling this spring include: A strategic listing plan with insightful guidance Accurate pricing based on current comparables Professional marketing and staging Flexible negotiation and realistic expectations Homes that are properly prepared and priced continue to sell, while unrealistic listings will sit longer and require price adjustments. The Bottom Line For both buyers and sellers, success this spring will come down to strategy, timing, and understanding the local market conditions. GET IN TOUCH As your trusted resource for all things real estate, we would be more than happy to provide you with additional insight on how to best prepare for buying or selling real estate. If you have any questions about the market, please reach out anytime. Want a better real estate experience? Call the Giles Team, we are always happy to help. NOT RECEIVING OUR NEWSLETTER? Send us an email so we can add your name and address to our monthly mailout. We look forward to connecting DK and Amanda
January 27, 2026
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Lower Prices As prices have come a fair bit over the last 2-3 years, combined with the aforementioned lower borrowing costs, some buyers will find attractive opportunities to secure ideal properties at more reasonable prices. Population & Immigration Trends Canada’s long-term immigration targets continue to support housing demand, especially in urban-adjacent regions like the Greater Golden Horseshoe, although population growth is now slower than we saw just a few years ago when prices were rising more significantly. Changing Buyer Preferences More buyers are turning to suburban and smaller city markets seeking affordability and space. This trend benefits areas outside Toronto, such as Hamilton, where prices are relatively lower and housing supply is expanding. 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What To Keep An Eye On The geo-political landscape has been changing rapidly throughout 2025 and this is likely to continue over the next few years. The effects of tariffs, international trade deals, territorial disputes, and more can and will have effects on many industries ranging from energy to agriculture, automotive to pharmaceuticals, tourism to housing, and just about everything else. Sometimes the effects can be positive and create opportunity, but it’s no secret that often there are serious negative impacts felt by many Canadians. Where and when there’s concern, consumer confidence is often eroded, especially if employment is at risk. Consumer confidence is surely going to play a role in whether or not some buyers choose to stay on the sidelines in 2026. Final Takeaway Ontario’s 2026 housing market is not going to be a repeat of the boom years, but it’s not likely to collapse either. Instead, we expect to see a maturing, more balanced market where economic fundamentals, buyer preferences, and demographic trends guide activity. Prices are adjusting, inventory remains elevated, and buyers have more room to negotiate – while sellers can still succeed with smart pricing and timing. Whether you’re considering selling, buying, or investing, understanding local market nuance is critical. 2026 will be a year where strategy matters more than ever before. GET IN TOUCH As your trusted resource for all things real estate, we would be more than happy to provide you with additional insight on how to best prepare for buying or selling real estate. If you have any questions about the market, please reach out anytime. Want a better real estate experience? Call the Giles Team, we are always happy to help. NOT RECEIVING OUR NEWSLETTER? Send us an email so we can add your name and address to our monthly mailout. We look forward to connecting DK and Amanda
By giles_donna September 17, 2025
Why Lower Interest Rates Are Good News for Ontario Homebuyers Thinking about buying a home in Ontario but have been holding back? You’re not alone — and the good news is, things may be starting to turn in your favour. Interest Rates Are Starting to Fall Over the past few years, rising interest rates made mortgages more expensive. This pushed monthly payments higher and caused many would-be buyers to hit pause on their plans. But now, the tide seems to be turning. Interest rates in Canada have started to come down gradually, and more cuts are expected. While it’s not happening overnight, the overall direction is positive. That means borrowing money to buy a home could get cheaper in the coming months. What Does This Mean for Buyers? Here’s why this shift in interest rates could be great news for you: 1. Lower Monthly Payments When interest rates drop, mortgage payments usually go down too. That means more manageable monthly bills — and that helps your overall budget. 2. Easier to Qualify for a Mortgage As borrowing costs fall, more people may find it easier to qualify for a home loan. This is especially important for first-time buyers who were previously priced out. 3. More Confidence to Enter the Market With some stability returning to the market and affordability improving, buyers who were waiting on the sidelines are starting to come back. That boost in confidence can also support home values in a healthy way — without things overheating. 4. Better Deals on Fixed-Rate Mortgages Fixed-rate mortgages — the ones where your interest rate stays the same for years — are also starting to become more competitive. This gives buyers more peace of mind with predictable payments. 5. Good Time for Investors Too Lower rates can also make rental properties more appealing. With lower mortgage costs and steady rental demand, investing in real estate could make more financial sense now than it did a year ago. When Will Buyers Feel the Impact? You might not notice the change instantly, but small rate cuts are already making a difference for people renewing their mortgages or looking to buy this fall. If current trends continue, the buying environment could keep improving into 2026. Final Thoughts If you’ve been thinking about buying a home in Ontario but felt the costs were too high, now might be a good time to start watching the market more closely. Falling interest rates could open the door for more affordable borrowing and renewed opportunities — whether you’re looking for your first home, a move-up property, or an investment. Just remember while rates are improving, it’s still important to run your numbers, work with a trusted mortgage advisor, and make sure the timing is right for your situation. _____________________________________________________________________________________________ GET IN TOUCH As your trusted resource for all things real estate, we would be more than happy to provide you with additional insight on how to best prepare for buying or selling real estate. If you have any questions about the market, please reach out anytime. Want a better real estate experience? Call the Giles Team, we are always happy to help. NOT RECEIVING OUR NEWSLETTER? Send us an email so we can add your name and address to our monthly mailout. We look forward to connecting DK and Amanda
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