Upsizing in Markham, Ontario — How to Move Up to a Larger Home Without the Stress

Why Upsizers Are Particularly Well-Positioned in Markham Right Now

The current Markham market — buyer-friendly across the board, with more inventory, more days on market, and sellers more willing to accept conditional offers — creates an unusually favourable window for upsizers. When you are selling a smaller Markham home and buying a larger one simultaneously, the gap between your sale price and your purchase price is what matters most. In a market where prices have softened across all property types, the absolute dollar softening on a $1,500,000 detached home is larger than the softening on a $900,000 semi or townhome. This means the price gap between what you are selling and what you are buying has actually compressed — the same transaction that seemed financially impossible at peak pricing may now be achievable.</ p>

The Upsizing Transaction — Three Approaches

Sell First, Then Buy

The sell-first approach eliminates financial exposure. You know exactly how much you will net from your sale before committing to a purchase price on your next home. The risk: you may need temporary accommodation between closing on your sale and moving into your new home. In the current Markham market, where many sellers are willing to negotiate flexible closing dates, a buyer who has already sold their existing home and is purchasing with certainty is in a strong negotiating position.

Buy First, Then Sell

The buy-first approach ensures you find and secure your next home before selling your current one. The risk is holding two properties simultaneously if your sale takes longer than expected. Bridge financing — a short-term loan that uses the equity in your sold home to fund the down payment on your new home during the gap between the two closings — is the standard financial tool for managing this risk.

Coordinated Simultaneous Closing

The ideal outcome for most Markham upsizers is a coordinated same-day or same week close — selling your current home on the same date or within a few days of closing on your new one. Achieving this requires negotiating both transactions with complementary closing dates, which is significantly easier in the current market where sellers are more flexible on timing than they were during the peak years.

What Markham Upsizers Are Buying Into in 2026

The most common upsizing moves in Markham in 2026 follow predictable patterns:</ p>

• From a condo or condo townhome to a freehold townhome: buyers who purchased a Downtown Markham condo or a Cornell or Greensborough condo townhome several years ago are now upsizing to freehold townhomes with private yards and more square footage as their families grow.
• From a freehold townhome to a semi-detached or detached home: Markham townhome owners are moving up to detached homes in communities like Wismer Commons, Cornell, and Box Grove — prioritizing school catchment access and yard space as children reach school age.
• From a semi-detached to a detached home: Markham semi detached owners with growing equity are moving up to detached homes in communities including Upper Cornell, Greensborough, and the established portions of Unionville and Markham Village.
• Into luxury: Established Markham homeowners with significant accumulated equity are entering the Angus Glen, Cachet, and Bayview Glen luxury tier.</ li>

The Tax and Financial Implications of Upsizing

Upsizing in Markham from a principal residence carries no capital gains tax on the sale of your existing home — principal residence exemption covers the full gain if the home was your primary residence throughout your ownership. However, the land transfer tax on your new purchase will be calculated on the full purchase price of your new home, at Ontario's standard LTT rate.

Budget for closing costs on your purchase of 3% to 5% of the purchase price, plus legal fees on both the sale and purchase side. Michael John Lau coordinates with your real estate lawyer and mortgage broker to ensure the financial picture is clear and complete before you commit to either transaction.