There is no age that answers this. What separates a good downsizing move from a difficult one is almost never the year it happened. It is whether the household was choosing or reacting.

A move made deliberately, over six to twelve months, with time to sort the house, prepare it properly and wait for the right purchase, tends to go well and tends to produce a better price on both sides. A move made in six weeks because circumstances changed tends to cost money in every direction at once.

So the practical answer is: start thinking about it while it is still entirely optional. The thinking costs nothing and it is what buys you the choice later.

This is the move people ask for most and the one that is hardest to execute, for a simple structural reason: Markham was built upward. The newer communities are almost entirely two storey, and bungalows are concentrated in the older parts of the city, where they were built in the 1950s through 1970s.

That creates a specific market. Bungalows on good lots in established areas are wanted by two completely different buyers: downsizers who want single-floor living, and builders or renovators who want the land. You are competing with the second group, and they are not valuing the house the way you are.

Three practical consequences. First, be ready, because the right one does not sit. Second, expect the house to need work, since most are sixty years old and many have original systems. Third, a bungalow is not necessarily cheaper than the two storey you are leaving, and in a good location on a large lot it can be more. The gain from this move is lifestyle, not always money.

Worth considering as alternatives: a two storey with a main-floor primary bedroom, which gives you single-floor living without competing in the bungalow market, or a condominium townhouse with a ground-floor bedroom. Both widen the search considerably.

People calculate downsizing as the price of their house minus the price of the new place, and treat the difference as money released. That number is always too high.

What actually comes off it: the cost of selling, the cost of buying, the cost of moving, the cost of getting the house ready to sell, and whatever you spend making the new place suit you. Those are covered in the next section, and together they are substantial.

Then there is the ongoing side, which is where the genuine case usually lives. A smaller home or a condominium generally means lower property tax, lower utilities, lower insurance and little or no maintenance spending, offset by a condominium fee if you go that route. Run those monthly numbers for both the current house and the realistic target, because the monthly improvement is often more meaningful than the lump sum and it compounds over a decade.

No figures appear in this guide, deliberately. Prices, tax rates, fees and costs all move, and a number written today misleads within months. Ask for current figures for your own house and your realistic target, and insist that the comparison includes everything in the next section rather than just the two prices.

Selling the house. Brokerage fees, legal fees, and whatever the house needs before photographs. Our guide to the cost of selling in Ontario sets out what comes off the top.

Buying the new place. Land transfer tax, legal fees, title insurance, adjustments on closing, and a home inspection or status certificate review.

Preparing the house to sell. After decades in a home this is usually more than people expect: paint, repairs that have been deferred, decluttering, sometimes staging.

Clearing the house. Movers, and separately the cost of dealing with what you are not keeping: disposal, junk removal, donation pickups, sometimes an estate sale or auction. On a full house this is a real number and it surprises people.

Storage, if your dates do not line up. Often unavoidable, and worth budgeting for rather than discovering.

Making the new place suit you. Window coverings, a few pieces of furniture that actually fit the new rooms, sometimes accessibility work. Almost nobody budgets this and almost everybody spends it.

Add all of that up before you decide whether the financial case works. If it only works when you ignore half of this list, it does not work.

Ask anyone who has done this and they will tell you the house sold fine and the contents nearly broke them. Thirty or forty years of accumulation, much of it attached to people and periods rather than to usefulness, and a deadline.

Start before you list, not after. Months before, if possible. A decluttered house also photographs better and shows better, so this work earns money as well as saving stress.

Measure the new place and work backwards. Decisions become far easier when the question is "does this fit" rather than "do I want this." The dining set, the piano, the bedroom suite and the bookcases are where it goes wrong.

Deal with the sentimental things first, not last. People leave them to the end, run out of time and energy, and then make rushed decisions about the items that actually mattered. Do those while you still have patience.

Be realistic about what family wants. Adult children frequently do not want the china, the furniture or the collections, and that is not a rejection of you. Ask early and believe the answer.

Know your routes for the rest. Donation, consignment, auction, estate sale, free pickup and disposal all exist and they suit different items. Our guides to where to donate furniture in York Region and estate sales and garage sales cover the options.

Downsizing is rarely a decision one or two people make alone. Adult children have opinions, sometimes strong ones, and they are usually a mix of genuine concern and attachment to the house they grew up in.

Two things make this go better. Have the conversation before you are viewing properties, so it is about the idea rather than about a specific purchase someone can object to. And be clear about whose decision it is. Input is valuable. A veto from someone who does not live there and is not paying for it is a different thing.

Where the proceeds are intended to help family, or where a family member may go on title or contribute, get that structured properly with a lawyer and an accountant at the start. These arrangements are straightforward when documented at the outset and extremely difficult to unwind later.

1. Calculating the gain as the difference between two prices. It is not. Count the full cost of moving before you decide the case works.

2. Not measuring. Estimating that your furniture will fit, then discovering on moving day that it does not. Measure the rooms and measure the furniture.

3. Buying a condominium without reading the reserve fund study. The single most expensive omission available in this process.

4. Assuming one parking space is enough, or that a second is available. Confirm what is included with the unit and what a second costs, if one exists at all.

5. Leaving the contents until after the house is listed. It delays everything, it shows badly, and it turns a manageable job into a crisis with a deadline.

6. Not stress-testing the condominium fee. Fees rise. A fee that is comfortable today on a fixed income should be tested upward over a decade before you commit.

7. Moving while the household disagrees. It produces a purchase one of you resents and sometimes a second move within three years. Settle it first.

Two things, almost without exception. That they should have started sorting the house a year earlier than they did. And that the thing they valued most was not the money released, but not thinking about the property any more.

The households who regret it are usually the ones who moved in a hurry, bought the wrong shape of home, or went somewhere unfamiliar and lost the routines that made their week work. All three are avoidable with time, which is the one resource this decision really needs.