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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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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What to Expect in Ontario's Housing Market in 2026

January 27, 2026
What to Expect in Ontario's Housing Market in 2026 As we settle into 2026, Ontario’s housing market continues to evolve in response to changing economic conditions, shifting buyer behaviour, and broader national trends. After several years of rapid price growth that reached a fevered pitch through the COVID-19 pandemic, we have experienced a period of cooling with many homeowners, buyers, and investors asking: What’s next? Here’s a look at what to expect in Ontario’s real estate landscape this year. Market Conditions: Balanced but Still Soft After a slowdown in 2025 that was characterized by price declines, elevated inventory, and subdued sales, the Ontario market is shifting toward a more balanced environment where neither buyers nor sellers hold overwhelming advantage. Inventory levels are likely to remain elevated, giving buyers more choices and reducing urgency to make offers quickly. But, sales activity may increase modestly in 2026, reflecting improved affordability thanks to lower prices and improved interest rates. This means we’re likely to continue seeing fewer bidding wars and fewer “above ask” offers compared with the frenzied market of 3-5 years ago. Price Trends: Modest Changes Ahead Of course, no one has a crystal ball, but unlike the sharp gains of the past decade, price movements in 2026 are expected to be moderate and regionally varied: Toronto Area Experts forecast slightly lower average prices in many core markets – particularly the GTA – with some projections from Re/Max Canada and Royal LePage suggesting a modest decline of around 3-5% year-over-year. Broader Ontario Other regions – especially smaller cities and some larger communities such as Hamilton, Burlington, and Oakville – may see stable to slightly positive price performance. Re/Max Canada is projecting up to 3% growth in average price for Hamilton and Burlington, while gains may be more muted in Oakville. Generally, mild gains could be experienced as demand shifts out to communities with greater affordability. The result? A market where some areas grow slowly, some hold steady, and others adjust downward slightly – reinforcing the idea that Ontario is not a single market but a collection of markets. That spectrum from one community to another isn’t likely to be broad, ranging from minor price dips to small price gains. Why This Is Happening Interest Rates & Borrowing Mortgage rates have been more stable following reductions by the Bank of Canada, which may encourage buyers who were previously sidelined by high borrowing costs. Stable or lower rates make monthly payments more manageable and could help draw buyers back into the market. 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. Key Opportunities in 2026 Whether you’re buying or selling, 2026 presents distinct opportunities depending on your goals: For Buyers More negotiating power: With inventory higher than in past years, buyers can take time to compare options and negotiate terms. First-time buyers may find opportunities in suburban and secondary markets where prices are more affordable. Stable interest rates make budgeting and planning easier. For Sellers Sellers in high-demand pockets – particularly in mid-sized cities and well-located urban neighborhoods – may still find strong buyer interest. Pricing your home realistically is key: overpricing in a balanced market can lead to much longer days on market and, ultimately, more price reductions. For Investors Rental demand in key Ontario markets remains healthy, though rental price growth has softened in some areas. Properties in transit-connected, high-employment areas, and near universities, remain more resilient. 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

Why Lower Interest Rates Are Good News for Ontario Homebuyers

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

Standing Out in a Crowd: How to Make Your Home Shine When Inventory Is High

July 16, 2025
Standing Out in a Crowd: How to Make Your Home Shine When Inventory Is High The work that goes into ensuring a successful sale is always important, but when the real estate market is flooded with listings, how your home is prepared, presented, and priced becomes critical. The idea that everything sells quickly with multiple offers and a high-dollar sale price by simply putting up for a “For Sale” sign just isn’t reality. In a high-inventory market, buyers have options – lots of them. That means your home needs to do more than just exist on the MLS; it needs to stand out. Here’s how to make your home the one buyers remember (and maybe even compete for) when inventory is abundant: 1. First Impressions Are Everything In a crowded market, buyers often scroll through dozens – if not hundreds – of listings online, sometimes for many months, before deciding to see some in person. Your home needs to stop the scroll. Pro tips: Ensure the front exterior is showing its best. Perform any needed repairs, repaint, clean up the gardens, and replace anything that should be replaced (i.e. front door, door hardware, exterior lights, etc). Hire a Realtor who will invest in professional photography, including drone shots and videography. If you’re unsure when you’ll be listing, consider having photography done in spring or summer when the weather is best, grass is green, and gardens are in bloom. Stage your home for photos, not just showings. A clean, bright, well-styled space photographs better and draws attention online 2. Price It Right – From Day One When buyers have choices, overpriced homes get ignored. You don’t want to be the "benchmark" buyers use to justify better-priced options Strategic considerations: Work with your Realtor to study comparable sales and current competition. Recognize that even if your sale price is a little less than you had hoped, chances are the purchase price of your next home will also be lower if completing both transactions in the same market. Consider pricing slightly under market to generate buzz and possibly spark multiple offers 3. Stage to Sell Empty or cluttered homes don’t capture imagination. Good staging helps buyers visualize living there. Focus on: Decluttering and depersonalizing. Highlighting focal points such as fireplaces, large windows, and open layouts. Creating a mood in each room that invites buyers to linger 4. Fix What’s Broken – Before Showings Begin Deferred maintenance is a red flag in any market. When buyers have alternatives, it can take your home out of the running entirely Check for: Leaky faucets, chipped paint, worn flooring, loose railings, burnt-out bulbs, old furnace filters, non-functioning garage door openers, and more 5. Upgrade Smartly You don’t need a full renovation to stand out, but a few updates can go a long way High Return of Investment (ROI) improvements include: New hardware and fixtures. Updated lighting. Fresh paint in neutral tones. Curb appeal enhancements (think mulch, power washing, re-sealed asphalt driveways, and fresh flowers) 6. Market Strategically A great listing deserves great marketing. In a high-inventory market, your Realtor should have a multi-platform strategy to increase visibility This should include: MLS exposure with a compelling description. As not all real estate boards use the same MLS system and/or share data, your listing really should be on all MLS platforms. Social media campaigns, including paid ads. Open houses, private showings, and possibly broker tours to reach wider audiences 7. Be Flexible and Responsive When supply is high, buyers can afford to be picky – not just about the home, but about communication and timelines Stay ahead by: Being accommodating with showings. Responding quickly to inquiries and offers. Considering all feedback seriously to make adjustments if needed Final Thoughts In a market where inventory is high, your competition isn’t just other homes – it’s buyer expectations. With the right preparation, pricing, presentation, and marketing, your home can rise to the top of a long list. The goal? Make buyers feel like they’ve seen the one – and not just another option. 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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