Thirty years in the same house, and no idea where to start.

OneYou don't have to decide today

Here is the honest truth about this decision. Almost nobody who is happy with how their move went made it in a hurry, and almost nobody who regrets theirs had a plan before they started.

The thing that makes this feel impossible is that it looks like one enormous decision, when really it is about six ordinary ones that happen to be sitting in a pile. Take them one at a time and they stop being frightening.

So here is the only thing we would ask you to accept before you read the rest. Finding out what your options are is not the same as agreeing to move. You can do all the research in this guide, decide you are staying exactly where you are, and be much better off for having done it, because now you know.

You do not need to rush. You do need to know your numbers before somebody else needs you to know them.

The reason we say that last part plainly: the families who end up in a difficult position are almost always the ones where the decision got made by an event rather than by a person. A fall, a diagnosis, a hospital discharge with a two week deadline. When that happens, the house gets sold quickly, the belongings get dealt with badly, and nobody has any good options left.

Doing this on your own timetable, while you are perfectly capable, is the whole point.

TwoThree questions that come before "should I sell"

People jump straight to what the house is worth. That is the fourth question. These are the first three.

What is actually bothering you?

Be specific with yourself. "The house is too much" is a feeling, not a problem you can solve. These are problems, and some of them have answers that are not a move:

• The stairs. Sometimes a stair lift or moving the bedroom to the main floor buys years.
• The maintenance. Sometimes a snow contract, a lawn service and a handyman on retainer costs a fraction of a move.
• The money. If the house is fine but the cash flow is not, that is a different conversation, possibly with a financial advisor rather than an agent.
• Being alone in it. That one a house cannot fix, and it is often the real answer.
• Distance from your children or grandchildren.

Write down the top two. If they are both solvable without moving, you have your answer and it did not cost you anything.

Where would you want to be?

Not what type of home. Where. Near which people, which streets, which grocery store, which doctor. A great deal of what makes a move work or fail is whether the new neighbourhood feels like somewhere you already belong.

People underestimate how much they will miss the walk they have done every morning for twenty years, and overestimate how much they will use the party room.

Who else is in this decision?

A spouse, obviously. But also: are your adult children going to be involved, and do you want them to be? Some people want their family in the room from day one. Others want to arrive at their own conclusion first and then tell everyone.

Both are fine. What causes trouble is when it is unclear, and one child finds out from another that you have been looking at condos.

ThreeWhere you could actually go

There are more options than most people realize, and they work in genuinely different ways.

A condominium apartment

You own your unit and a share of the building. Monthly fees cover the building's maintenance, usually the reserve fund, often water and sometimes heat. The trade is that somebody else shovels the snow, and you are no longer in charge of the roof. The most common complaint from people who move into one: the fees go up. The most common relief: never thinking about the furnace again.

A freehold or condo townhome, or a bungalow

Less house, still your own front door, often a small yard. This suits people who want out from under a big property but are not ready for apartment living. In York Region, adult lifestyle and 55+ communities frequently take this form, with a clubhouse and a monthly fee for the shared facilities.

A retirement residence

Private pay, month to month, licensed by the Retirement Homes Regulatory Authority. Meals, housekeeping, activities and staff on site, with care available and charged separately as you need it. Independent suites across Ontario generally run from about $3,000 to $4,500 a month, with larger or premium suites from $4,500 to $6,500, and care levels added on top of that. In York Region and Toronto, expect the upper half of those ranges.

Worth knowing that this is a rental, not a purchase, and you can give notice and leave. People often assume it is a bigger commitment than it is.

Rental, and life lease

Ordinary renting is a legitimate choice, particularly if you want to try a neighbourhood before committing, and it keeps your capital liquid. Life lease is different and needs care: you pay a lump sum for the right to occupy a unit, usually for life, in a building owned by a non profit or faith based sponsor. You do not own the property. The rules on resale, on what comes back, and on who can inherit the interest vary enormously between projects. Have a lawyer read the agreement before you sign anything.

Long-term care

Worth naming so it is not a mystery. It is government funded nursing care for people who need it around the clock. You cannot buy your way in, placement is assessed and arranged through Ontario Health atHome, and the province sets the rate. As of 1 July 2026, basic accommodation is $70.00 a day, or $2,129.17 a month, and there is an income based rate reduction for people who cannot afford it. This is not a downsizing option, it is a care option, and most people reading this are nowhere near it.

FourThe number that decides most of it

Here is where people go wrong. They look up what houses on their street sold for, subtract what they think a condo costs, and conclude they will have a pile of money left over. Then they get to the lawyer's office and the pile is a great deal smaller.

The number that matters is not the sale price. It is what is left after everything, and then what the new place costs to get into and to run.

Out of the sale

• Any mortgage or line of credit secured against the house
• Real estate fees, plus HST on them
• Legal fees and disbursements
• Anything you spend getting it ready, plus the clear out and the move

Into the purchase

If you are buying rather than renting, Ontario land transfer tax comes off the top. It is worth seeing in real numbers, because most people have not bought a home in decades and the amounts have changed a great deal.

Toronto charges its own municipal land transfer tax on top of the provincial one, which is why buying a condo downtown costs roughly twice as much in tax as buying the same priced condo in Markham or Newmarket. Add legal fees, title insurance, and moving costs on top.

Then the monthly cost of the new place

People compare a paid off house against a condo and forget that the house was not actually free. Do it properly, on one page, side by side:

Fill it in honestly and the answer is usually clear one way or the other, and often it is not the way people expected.

If you are looking at a condominium, ask for the status certificate and have your lawyer read it before you are committed. It tells you whether the reserve fund is healthy, whether a special assessment is coming, and whether the corporation is in litigation. It is one of the most useful documents in the transaction, and a great many buyers never really look at it.

We will prepare the whole picture for you in writing, what your home would realistically sell for with the comparable sales attached, what is left after every cost, and what the monthly comparison looks like. There is no charge, and no obligation to list with us or with anyone.

FiveWhat your house needs, and what it doesn't

The most expensive advice you can get is that you need to renovate before you sell. Usually you do not.

Worth doing, nearly always:

• Decluttering. This is usually where the effort pays back best, and it costs nothing but time.
• A deep clean, including windows and carpets.
• Paint, if the walls are actually marked. Neutral.
• Fixing what is broken or unsafe. The loose railing, the dripping tap, the light that does not work.
• The yard tidied and the front door looking cared for.

Usually not worth doing:

• A new kitchen or bathroom. In most of York Region, a well kept but dated home in a good location sells to a buyer who plans to renovate to their own taste. You will not choose the tile they wanted.
• New windows or a finished basement.
• Anything that means living in a construction site while you are also trying to sort out a move.

Worth knowing about: if the furnace, roof or windows were done recently, find the receipts. Documented recent work does more for a buyer's confidence than new work does for the price.

If you do nothing else, empty it. In our experience an older home shows far better clean, bright and empty than it does full of thirty years of furniture.

SixThirty years of belongings

This is the part everybody dreads, and the part that stops most people from starting. So here is the only trick that reliably works: do it in the wrong order on purpose.

Do not start with the photographs. Do not start with your mother's china. You will spend four hours in a chair with a shoebox and stop for a month.

Start with the decisions that are arithmetic rather than emotion.

1. Get the floor plan of a place you are considering, even if you have not chosen it yet. Measure the rooms. Now you know what fits, and what comes with you stops being a matter of feelings.
2. Furniture first. Your own comfort wins. The chair you sit in every single evening comes. The formal dining set for twelve that gets used twice a year probably does not, even though it was expensive, and it is allowed to be sad about that.
3. Then the everyday things. Kitchen, linens, the garage, the basement shelves. Volume comes down fast here.
4. Sentimental things and paperwork last, when the pressure is off and you have time to sit with them properly.

Two practical notes. Movers book up at month ends and right through the spring and summer, so book early, and if you can move mid month and mid week it is cheaper and calmer. And be prepared for the fact that the market for large wooden furniture, china cabinets and formal dinnerware is very soft right now, which says nothing at all about what those things were worth to you.

If it would help to have somebody alongside you for the sorting, a professional organizer does this for a living and is worth every dollar.

SevenBuy first, or sell first

Both work. They carry different risks, and the right answer depends on which risk you would rather hold.

There is a middle path that gets used more than either extreme: sell with a longer closing, ninety days or more, which gives you time to find the next place with the sale money already certain. If you are renting rather than buying next, this problem largely disappears.

EightWhat people tell us they regret

Not the move itself. Almost nobody who does this on their own terms regrets the move. What they regret is more specific.

• Waiting until they had to. By far the most common. The people who move on their own schedule are noticeably more settled about it afterward than the people who move after a fall.
• Going too small too fast. A one bedroom is cheaper, but people who go from a house to a small apartment in one step often struggle. A townhome or a two bedroom is a gentler step, and the second bedroom becomes the office, the sewing room, or the place a grandchild sleeps.
• Choosing the building and not the neighbourhood. The suite you tour for twenty minutes matters far less than whether you can walk somewhere worth walking to.
• Not reading the status certificate. A special assessment eighteen months after moving in is a horrible surprise and an avoidable one.
• Letting one adult child drive it. Well meant, and it often ends with the other children resentful and the parent feeling managed.
• Renovating first. Money spent, stress endured, and rarely paid back.

And the thing nobody regrets: starting the conversation earlier than they needed to.

NineA six month plan that commits you to nothing

• Month 1 Work out what is actually bothering you

  Write down the top two things. Decide whether either has an answer that is not a move. If they both do, you are finished, and it cost you an evening.

• Month 2 Look, without committing

  Browse the directory. Drive the neighbourhoods you might want. Walk into two or three buildings and ask for a tour. You are gathering information, not shopping.

• Month 3 Get your numbers

  A written estimate of what your home would sell for and what is left after everything. The monthly comparison, side by side. Now the decision has actual figures in it.

• Month 4 Decide, or decide not to decide yet

  Both are legitimate outcomes. If you are going ahead, choose the type of home and the area, and settle whether you are selling first or buying first.

• Months 5 to 6 Start sorting, and get the house ready

  Floor plan, furniture, everyday things, sentimental last. Clean, paint, tidy the yard. Book the mover early. Then list.

Nothing in months one through three commits you to anything at all. That is deliberate. Most people need to see the numbers before they can tell how they feel about the decision, and there is no way to see the numbers without doing a bit of the work.

TenThe checklist

• Write down the two things that are actually bothering youAnd whether either one has a fix that is not a move.
• Decide who else is in this decision, and tell themBetter they hear it from you than from each other.
• Look at what is out there before you talk to anybodyThe directory is free and there is no form.
• Visit at least three places, in personGo at a mealtime. Talk to somebody who lives there.
• Get a written estimate of your home's value with the comparablesNot a number off a website.
• Work out your net proceeds, not your sale priceAfter the real estate fees, HST, legal fees, the move and the clear out.
• Confirm the principal residence exemption applies to youAn accountant, if you also own a cottage or a rental.
• Budget land transfer tax on the purchaseRoughly double inside the City of Toronto.
• Fill in the monthly comparison, both sidesProperty tax, insurance, utilities, fees, maintenance, and what is coming.
• Read the status certificate before you commit to a condoWith your lawyer. Reserve fund, special assessments, litigation.
• Make sure you have a will and both powers of attorneyProperty, and personal care. Separate documents. Do it while it is easy.
• Start sorting with the floor plan and the furnitureNot with the photographs.
• Book the mover early, and mid month if you canMonth ends and summer fill up first.