As a cofounder of Kaizen Real Estate Team, one of the teams Markham families call when they are ready for their next chapter, Neeraj Moolchandani helps clients with this decision often. There is no single right answer. There is only the right answer for your situation.

Option One: Sell First

You sell your current home, then buy your next one with a firm budget.

Why it helps

• You know exactly how much money you have to work with.
• You never carry two homes at once.
• You negotiate your purchase with confidence, not fear.

The risk

If you do not find the right home in time, you may need a short rental or a longer closing. Most sellers handle this by asking for a longer closing date when they sell.

Option Two: Buy First

You find and secure your next home, then sell your current one.

Why it helps

• You get the home you want without rushing.
• You move once, on your own schedule.
• It can work well if the home you want is rare, such as a specific street or school area.

The risk

If your current home sells for less than expected, or takes longer, you may carry two mortgages and feel pressure to accept a lower offer. That is the situation we work hardest to help clients avoid.

What the Markham Market Is Telling Us

In September 2026, Markham had about 4.6 months of inventory. That is a balanced market. Homes sold for about 98 percent of asking on average, and took about 34 days. In a balanced market, it is harder to predict exactly when and for how much a home will sell, which is why selling first is usually the safer choice.

The details by home type matter too. Semi detached homes had only about 2.3 months of supply and sold for about 101 percent of asking. Detached homes had about 4.3 months. So if you own a semi and want to move up to a detached home, you may be selling in a tighter segment and buying in a more balanced one. That can work in your favour.

The Middle Path Most Families Choose

You do not have to pick an extreme. These tools help line up both sides:

1. List first, buy quickly. Prepare and list your home, and start looking at the same time. Once you have a firm sale, you shop with certainty.
2. Ask for a flexible closing. A longer or flexible closing when you sell gives you time to find your next home.
3. Make your purchase conditional on your sale. Some sellers will accept this, especially in a balanced market. It protects you, though it can make your offer less attractive.
4. Arrange bridge financing. A bridge loan covers the gap when your purchase closes before your sale. It costs interest and usually needs a firm sale in place, so talk to your lender early.

A Note for Downsizers

If you are moving to a smaller home, you may have a lot of equity and little or no mortgage. That gives you more freedom to buy first. The bigger challenge is often time: sorting decades of belongings, preparing the home, and planning a move your family is comfortable with.

Start with a plan for the sale, then match the purchase to it. See our downsizing guide for a step by step approach.

Questions to Ask Before You Decide

• What is my home realistically worth today, based on recent sales near me?
• How much equity will I have after the mortgage, closing costs, and moving costs?
• Could I carry two homes for one to three months if I had to?
• How rare is the home I want to buy?
• Would a short rental be acceptable if timing does not line up?

A free home valuation answers the first question and makes the rest much easier.