Upsizing in Markham, Ontario is one of the most strategic moves homeowners can make as their needs evolve. Whether transitioning from a condo to a freehold property or moving from a townhome to a detached house, the process involves careful coordination of timing, finances, and market conditions. While it may seem complex, the right approach can turn this into a smooth and highly rewarding experience.

Michael John Lau and Neeraj Moolchandani of Kaizen Real Estate specialize in helping Markham homeowners successfully upsize with confidence. Their experience in managing simultaneous buy and sell transactions ensures clients minimize risk while maximizing opportunity in both sides of the deal. From pricing strategy to negotiation and timing, their guidance simplifies what is often considered one of the most challenging real estate transitions.

Why Upsizing in Markham Is a Smart Move 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. Here is why.

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.

Add to this the fact that bridge financing is more readily available in the current environment,
sellers are more willing to negotiate closing dates that align with your purchase, and the
current Markham market may be the most practically navigable upsizing window in several
years.

The Upsizing Transaction, Two 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. Your mortgage broker can advise on bridge financing availability and cost based on your specific situation.

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.

From a Markham 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 home 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.

From within Markham to a luxury detached home: Established Markham homeowners with significant accumulated equity are entering the Angus Glen, Cachet, and Bayview Glen luxury tier, purchasing custom estate homes that reflect the full success of decades of Markham homeownership.

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.

For first-time buyers who have not previously owned a home, the LTT rebate of up to $4,000 is available, but most upsizers are not first-time buyers and will not qualify.

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 and Neeraj Moolchandani coordinate with your real estate lawyer and mortgage broker to ensure the financial picture is clear and complete before you commit to either transaction.

FAQ 

Is now a good time to upsize in Markham?
Yes. Current market conditions are favorable for upsizers due to increased inventory and more flexible sellers.

Should I sell first or buy first?
Selling first reduces financial risk, while buying first ensures you secure your ideal home. The right choice depends on your situation.

What is bridge financing?
Bridge financing is a short-term loan that helps cover the gap between buying your new home and selling your current one.

How much are closing costs when upsizing?
Typically 3% to 5% of the purchase price, plus legal and additional fees.

Do I pay capital gains tax when upsizing?
No, if the home is your principal residence, it is exempt from capital gains tax.

If you are thinking about upsizing in Markham, now is the time to explore your options and create a strategy tailored to your goals.

Michael John Lau and Neeraj Moolchandani are here to guide you every step of the way, ensuring a smooth transition into your next home.

Contact Kaizen Real Estate today
📞 Call 647-370-8885
📧 Email: [email protected]
🌐 Visit www.kaizenrealestate.ca
🗓️ Book a meeting today