Upsizing in Toronto: Should You Buy First or Sell First?

Updated October 2026 · Written by Candice Schott, Broker, Schott & Co., Royal LePage Signature Realty, Brokerage

For most Toronto upsizers right now, the safer order is to sell first with a longer closing, then buy with a firm sale in hand. Buy first only if your current home is the kind that sells fast and you can qualify to carry both homes for a while.

In September 2026, Toronto condos took 40 days on average to sell at 97% of asking, while semis sold in 21 days at 104% (TRREB). If you're moving from a condo to a house, you're selling in the slow market and buying in the fast one. This guide from Candice Schott, Broker and co-founder of Schott & Co., walks through both orders, bridge financing, land transfer tax, your mortgage and timing.

Should you buy first or sell first when upsizing in Toronto?

Sell first in most cases. Selling first tells you exactly how much equity you have, removes the risk of owning two homes, and makes your offer stronger, because you can buy without a condition on the sale of your home. Buying first gives you certainty on the new house, but if your current home sells slowly or for less than you planned, you carry two mortgages, two sets of property taxes and two sets of bills until it does.

"My usual answer is sell first with a longer closing, then walk into offer night with a firm sale in hand. To a seller, that's the cleanest offer in the room." — Candice Schott

Why does selling first make more sense in Toronto right now?

Because Toronto is really two markets. In September 2026, City of Toronto condo apartments averaged 40 days on market and sold for 97% of asking, according to TRREB. Semi-detached homes averaged 21 days and sold for 104%. In Leslieville and Riverdale (TRREB district E01), semis sold for 113% of asking in 12 days on average. If you're selling a condo and buying a house, the home you're selling is the slower one, so lock in that sale first.

A softer market can still work in your favour. Say your condo is worth $700,000 and the house you want is $1.4 million. If both drop 5%, you lose $35,000 on the sale but save $70,000 on the purchase. For this month's numbers, see our Toronto market report or Toronto Market Check.

When does buying first make sense?

Buying first can work when three things are true. Your current home is in high demand, such as a semi in Leslieville, Riverdale or The Beach, where inventory was under 2.5 months in September 2026. Your lender confirms in writing that you can carry both mortgages or will qualify for bridge financing. And the home you're buying is rare enough that you don't want to risk losing it.

Even then, list quickly. The stress test still applies to a new mortgage: federally regulated lenders must qualify uninsured borrowers at the greater of their contract rate plus 2% or 5.25%, per the Office of the Superintendent of Financial Institutions (OSFI).

What is bridge financing and how does it work?

Bridge financing is a short-term loan that lets you use the equity in your current home to close on your new one before your sale closes. Say your purchase closes on March 1 and your sale closes on March 20. A bridge loan covers your down payment for those 19 days, then gets paid off from your sale proceeds. Most lenders only offer it once your sale is firm, and they set their own limits on the amount, number of days and rate.

"Once your sale's firm, bridge financing can cover the gap between the closings. Your lender sets the terms, so talk to them early, like now." — Candice Schott

Should you buy conditional on the sale of your home?

Only in a slower market or for a less competitive home. A sale condition means your purchase depends on your current home selling by a set date. In competitive areas like Leslieville or The Beach, sellers usually pick a firm offer over a conditional one. Sellers who do accept a sale condition often add an escape clause, which lets them keep marketing the home and give you a short deadline to firm up if a better offer comes in. It can work on a home that's been on the market for a while. It rarely wins on offer night.

How much does it cost to move up in Toronto?

More than most people budget for. The biggest surprise is usually land transfer tax. Buy inside the City of Toronto and you pay it twice, once to Ontario and once to the City, and repeat buyers don't get the first-time buyer rebates.

Also budget for real estate fees on your sale, legal fees on both deals, any mortgage penalty, moving costs and bridge financing interest. Our Upsizing Calculator adds it all up with your own numbers.

How much down payment do you need to move up?

It depends on the price. Since December 15, 2024, homes up to $1,499,999 can be bought with an insured mortgage, according to the Department of Finance Canada. The minimum down payment is 5% of the first $500,000 and 10% of the rest, so $115,000 on a $1.4 million home, plus a mortgage insurance premium. At $1.5 million and up, the minimum is 20%. Most upsizers put at least 20% down from their equity to avoid the premium.

What happens to your mortgage when you upsize?

You have three main options. You can port your mortgage, moving your current rate and balance to the new home and adding new money at a blended rate. You can break it and take a new mortgage, which usually means a prepayment penalty. Or you can time your move around your renewal date, when you can switch without one.

For a fixed-rate mortgage, the penalty is usually the greater of three months' interest or the interest rate differential, which can be large, according to the Financial Consumer Agency of Canada. Ask your lender for the exact amount in writing before you list.

Do you pay tax when you sell your home?

Usually not on your principal residence. If it was your principal residence for every year you owned it, the principal residence exemption generally means no capital gains tax. You still have to report the sale on your tax return and designate the property, according to the Canada Revenue Agency. If you rented part of it or owned another property at the same time, talk to an accountant first.

How do you sell your current home for the best price?

1. Price it for this market, not for what your neighbour sold for in 2022.
2. Fix the small stuff first. Grout, bulbs, closets. Buyers notice the cheap fixes before the beautiful ones.
3. Launch with a plan: prep, photos, pricing and an offer strategy.

"The condos sitting for 60 days aren't bad condos, they're just overpriced condos." — Candice Schott

How long does it take to upsize in Toronto?

Plan on three to six months from your first call to moving day: two to four weeks to talk to your lender, prepare your home and set a price; one to four weeks to sell; then a 60 to 120 day closing while you buy your next home with a firm sale in hand.

Where do Toronto upsizers move to?

It depends on what you're moving up to: more bedrooms, a yard, parking or a shorter walk to the subway. Explore our neighbourhood guides:

• Leslieville: Victorian and Edwardian row houses and semis
• Riverdale: Victorian and Edwardian semis and detached homes
• Danforth Village: brick semis, small detached homes and bungalows
• East York: pre-war detached homes and post-war bungalows with yards
• The Beach: early 1900s detached homes, semis and cottages
• Leaside: detached and semi-detached brick houses
• Don Mills: mid-century bungalows and split-levels on wide lots

Common questions about upsizing in Toronto

Sources: TRREB Market Watch, September 2026 · Government of Ontario, land transfer tax · City of Toronto, municipal land transfer tax · OSFI, minimum qualifying rate · Department of Finance Canada, mortgage reforms · FCAC, prepayment penalties · CRA, principal residence

General information, not legal, tax, mortgage or financial advice. Talk to your lender, lawyer and accountant about your situation. Market figures are TRREB averages and vary by street and property. Not intended to solicit buyers or sellers currently under contract.