If you’re planning a move in 2025 – whether you’re upsizing to make room for a growing family, downsizing for a simpler lifestyle, or simply switching neighbourhoods for a better commute or school district – you’re likely wrestling with a crucial question: should you buy or sell first?
It’s one of the most common and anxiety-inducing dilemmas facing Toronto homeowners right now, especially in a market that’s shifting month to month. With inventory levels, mortgage rates, and buyer demand in flux, the order in which you move can significantly impact your stress levels, your finances, and your ability to land the right home.
The truth? There’s no universal answer – but there is a strategy that’s right for your unique situation. This guide breaks down the pros and cons of each option in the context of today’s Greater Toronto real estate market. Whether you’re feeling the pressure to secure your dream home before it’s gone, or worried about holding two mortgages, we’ll help you make the smartest move possible – whether you decide to buy or sell first.
Option 1: Buying First
Positive Outcomes to Buying First
If you’re leaning toward buying first, it’s still essential to consider your full buy or sell strategy – especially when timing and finances are tight.
Shop with clarity, not compromise.
When you buy first, you can take your time to explore neighbourhoods, school zones, and layouts that actually fit your family’s lifestyle. Whether you need a bigger backyard, a dedicated home office, or space for multigenerational living, you’re not settling just to match a sale timeline.
Smooth transition with fewer disruptions.
Moving once – directly from your old home into your new one means you skip the chaos of temporary storage, hotel stays, or cramming the kids into a rental for a month. This approach minimizes stress and keeps family routines more intact.
You’re in control of your next chapter.
You secure your future home before making any commitments on your current one. That’s peace of mind, especially when availability in your target neighbourhood is tight or properties are moving quickly.
Possible Concerns When You Buy First
Carrying two homes – even briefly can be costly.
If your current home hasn’t sold yet, you may find yourself paying two mortgages at once. That financial overlap can feel like a heavy lift, especially if it stretches beyond a few weeks.
You’ll need a financial cushion or bridge financing.
Lenders may require you to qualify for both homes temporarily. If your equity is tied up in your existing property, you might need interim financing or significant savings to close on the new one.
You’re betting on a strong sale.
This option works best when you’re confident in your home’s value and marketability – whether because it’s move-in ready, in a high-demand area, or professionally marketed by an agent who knows how to position it right (like The Halyard Group).
Best for: Families with specific location needs, those upgrading to a larger home, or anyone prioritizing stability over speed. Ideal when the buying side feels more competitive than the selling side.
Of course, choosing whether to buy or sell first depends on your finances, flexibility, and family needs.
Option 2: Selling First
Positive Outcomes to Selling First
Selling first can be the smart move for many families -but deciding whether to buy or sell first depends on a few key factors.
You’ll know your numbers.
Once your current home sells, you’ll have a crystal-clear understanding of your net proceeds – allowing you to search for your next home with a defined budget and financing already in place.
Avoid the financial juggling act.
You eliminate the need to carry two mortgages or rely on bridge loans. It’s a leaner, more conservative financial move, especially helpful in uncertain market conditions.
Stronger negotiation position.
With your home sold, you’re often viewed as a more attractive buyer – especially if you’re flexible on closing dates. Sellers love buyers who aren’t contingent on another deal closing.
Concerns With Selling First
You’re working with a ticking clock.
Once your home is sold, the pressure’s on to find something new – especially if you’ve committed to a tight closing window. If inventory is low, you might not find the perfect fit right away.
Temporary housing may be part of the plan.
If timelines don’t align, you could face a gap between homes. That might mean a short-term rental, living with family, or storing your belongings while you wait.
You might have to compromise.
With limited time, you may need to be flexible on your wish list – whether that’s square footage, commute time, or finishes.
Best for: Homeowners who want financial clarity before committing to a purchase. Great for those who are timeline-flexible or open to renting temporarily between moves.
How to Decide in 2025
There’s no one-size-fits-all approach, but when you’re trying to decide whether to buy or sell, a tailored plan can make all the difference.
Toronto’s 2025 housing market is balanced but complex. Some neighbourhoods move fast – especially those near top schools or green space – while others allow for more strategic timing. The good news is that either approach – buying first or selling first – can work, as long as it’s matched with the right plan.
Questions to Narrow Down What Works for You
Do I need the equity from my current home for the next down payment?
Selling first may give you the financial clarity and purchasing power to move confidently into your next chapter.
How comfortable am I carrying two homes, even for a short time?
If juggling two mortgages doesn’t align with your risk tolerance, or your budget is tight, buying first could be more stressful unless you have solid financing in place.
Can we negotiate flexible timelines?
In many cases, yes. We routinely help families lock in long closing periods, craft compelling offers with sale conditions, or even arrange post-sale rental-back agreements – so they’re never rushed out the door.
Final Thoughts
There’s no one-size-fits-all answer to whether you should buy or sell first – but with the right guidance, you don’t have to navigate that decision alone. At The Halyard Group, we specialize in helping families upsize with less stress and more confidence by tailoring every move to your timeline, goals, and financial comfort.
Not sure whether to buy or sell first? Let’s talk through your options together. We’ll help you build a strategy that works in today’s market – and for your family’s future.
It all starts with a simple conversation.
Book your complimentary 15-minute planning call with our team – no pressure, just personalized advice from people who understand what you’re navigating.
