Should You Sell First or Buy First When Downsizing in Waterloo Region?

Nicole Schell, Broker and Seniors Real Estate Specialist (SRES®) with the Schell Real Estate Team at Peak Realty Ltd. in Waterloo Region, hears one question from downsizers all the time: “Should I buy first or sell first?” There is no single answer that fits everyone. Both options have benefits and risks, and the best choice depends on your situation, your timeline, and what helps you sleep at night.

Adapted from a social post Nicole originally shared in June 2026.

The Two Questions I Ask in Return

When someone asks me this, I usually ask two questions back. The first tells me what options are available to you. The second shows me what would make you most comfortable during the transition. For most downsizers, the real issue is peace of mind:

Would you rather know exactly where you are moving before you sell, or know exactly how much money you have before you buy?

Your answer usually points us in the right direction.

Selling First

When you sell first, you know exactly how much money you have to spend, and you never carry two homes at once. The risk is timing: you need somewhere to go if you have not found your next home by closing. A longer closing date or a short term rental can give you breathing room.

Buying First

Buying first means you can take your time finding the right place and move without rushing. The risk is carrying two homes if yours takes longer to sell than expected, along with the pressure to accept a lower offer. Some buyers in this position use bridge financing, a short term loan that covers the gap between the two closings. Your lender or mortgage broker can tell you whether you qualify.

Options in Between

• Buy with a condition on the sale of your current home. This protects you, though sellers in a busy market may prefer an offer without it.
• List your home and start looking at the same time, so the two closings can be lined up as closely as possible.
• Negotiate closing dates that give you a few days of overlap for moving and cleaning.

Why the Conversation Should Start Early

Understanding what your current home is worth, what you can afford, and what options are available makes this decision much easier when the time comes. That is why I believe the conversation should start before you are ready to move. It is one of the reasons I created my Transition with Care approach: to help people understand their options, move at their own pace, and make decisions with confidence.

A Downsizing Discovery Call is a relaxed way to start. You can also read more on the Downsizing in Waterloo Region page, or reach out to start the conversation.