A great many of the houses I am asked to value in Richmond Hill, Markham and Thornhill were bought new, in the subdivisions that went up through the eighties and nineties, by the people who still live in them. The children have left, the stairs have become a nuisance, and the garden that was the point of the house has become the chore that fills every Saturday. Downsizing after that long is not a normal sale. The house is usually worth far more than it cost, it usually needs work its owners stopped noticing years ago, and the next home is harder to find than people expect. Here is how I would think it through.
Decide Where You Are Going Before You Decide When
The most common mistake I see is listing first and working out the destination later. After thirty years, the decision about the next home is the hard one, and it shapes everything else: the timing, the price you need, and whether you can afford to wait for the right buyer.
In York Region, downsizers tend to end up in one of four places:
- A condo apartment, often along the Yonge and Highway 7 corridor around Langstaff and Richmond Hill Centre, in Markham Centre, or near the Vaughan Metropolitan Centre, where the subway already runs.
- A bungalow. Everyone wants one and few were built. In most of the post-1980 subdivisions the stock is two-storey, so the bungalows that exist, mostly in older pockets, are contested by every other downsizer in the area.
- A townhouse or smaller detached house in the same neighbourhood, to keep the doctor, the church, the friends and the grocery store.
- Moving in with, or next to, family, which in this part of the GTA often means a larger house with a self-contained suite rather than a smaller one.
Each of these leads to a different sale. A buyer who has a condo closing fixed by a builder has no flexibility on dates. Someone hoping for a bungalow may need to buy first and sell second, because the right one may only come up once in a season.
The Gap Between the Two Prices
TRREB’s September 2026 figures put the GTA-wide average detached price at $1,292,016 and the average condo apartment at $605,257. Those are averages across the whole region, not a quote for your street, and the gap on any individual sale will be different. But they show why downsizing is usually how long-time owners turn their house into retirement money.
The gap shrinks faster than people expect. Moving a house full of thirty years costs money. If the next home is in Toronto, including North York, you pay both the provincial and the Toronto municipal land transfer tax, which is a meaningful extra cost compared with buying in York Region, where only the provincial tax applies. Condo fees replace the roof and furnace fund you used to keep in your head, and they rise. A realistic budget lists all of this before you decide how much is left over.
Whether any of the gain is taxable depends on your circumstances, such as whether the house was always your principal residence. That is a conversation for your accountant before you list, not after you close.
What Thirty Years Does to a House
A house its owners have lived in for three decades has usually been well kept and rarely updated. The furnace has been serviced, the lawn is perfect, and the kitchen, bathrooms and windows are original or close to it. Buyers see that immediately.
The temptation is to renovate before selling. Usually that is a mistake. In the older subdivisions of Richmond Hill and Markham, many of the people who buy a dated house plan to renovate it to their own taste, and they price that in whatever you do. A new kitchen you choose is a kitchen they would have chosen differently. What does pay is the boring work: fix what is broken, clear thirty years of belongings so the rooms look their real size, paint where it is tired, and deal with anything an inspector will flag, such as an old electrical panel, a roof near the end of its life or signs of water in the basement. Our separate guide on what to fix before listing, and what to leave alone, goes through this in detail.
On some streets the lot is worth more than the house. In parts of Richmond Hill and Thornhill with large lots and older homes, the strongest buyer may be a builder or a family who plans to rebuild. That buyer is not interested in fresh paint, and a seller who knows that can save the cost of preparing the house for the wrong audience.
Timing the Two Moves
There are three ways to do it:
- Sell first. You know exactly what you have to spend, and you are never carrying two homes. The risk is having to rent, or move twice, if the next home does not turn up in time.
- Buy first. You choose the next home without pressure, which matters if you need a bungalow or a particular building. The risk is carrying both, and needing bridge financing if the sale takes longer than planned.
- Line the closings up. Possible, but it needs a buyer willing to accept your closing date and a seller willing to accept your conditions. In a slower market, with more choice for buyers, it is more achievable than it was a few years ago, but it is not something to assume.
A mortgage broker or your bank can tell you before you start whether bridge financing is available to you and on what terms, which is the single fact that decides between the first two options.
The Things Nobody Mentions
Sorting thirty years of belongings takes months, not weeks. Start before you list. Showings go better in an emptier house and the move goes better without a deadline on top of it.
Read the condo documents. If you are buying a resale condo, the status certificate and the reserve fund study tell you whether a special assessment is coming. Have your lawyer review the status certificate as a condition of the offer.
Check the building, not just the unit. Number of elevators, how parking and lockers are assigned, whether there are rules about pets or renovations. These are the details that make a building liveable for the next twenty years.
Involve the family early, especially if the house is held jointly, if a power of attorney is involved, or if adult children expect to be consulted. A disagreement that surfaces after an offer arrives is far more expensive than one settled in advance. Questions about title, estates or powers of attorney belong with your lawyer.
Frequently Asked Questions
Should I renovate my house before downsizing?
Usually not a full renovation. Fix what is broken, deal with anything an inspector will flag, declutter and paint. Many buyers of older homes plan to renovate to their own taste anyway.
Should I sell my house first or buy my next home first?
It depends on how hard the next home will be to find and whether you can arrange bridge financing. Ask a mortgage professional what you qualify for before deciding.
Is moving from York Region to a condo in North York more expensive to close?
Generally yes, because North York is part of Toronto and buyers there pay the Toronto municipal land transfer tax on top of the provincial one.
Do I pay tax on the profit from selling my family home?
That depends on your circumstances, including whether the home was always your principal residence. Ask an accountant before you list.
Why are bungalows so hard to find in York Region?
Most subdivisions built since the 1980s are two-storey, so the bungalows that exist are few and are sought by every other downsizer in the area.
Thinking about leaving a house you have lived in for decades in Richmond Hill, Markham or Thornhill? Reach out for seller representation and we can work out what the house is worth to the buyers most likely to want it, and what that leaves for the next home, or start with how the Richmond Hill market is behaving.