The question arrives in my inbox at least once a week, and it usually shows up on a Monday: is now a good time to buy or sell? I have been tempted to answer it with a forecast, because a forecast is what the question sounds like it wants. I am not going to. I would rather tell you what the question is actually made of, and let you answer it for your own situation.
So here is the walk through: why the question is shaped wrong, what a forecast is worth, and what actually decides this.
THE QUESTION IS ASKED EVERY WEEK, AND IT IS SHAPED WRONG
When somebody asks whether it is a good time to buy or sell, they are usually asking three questions at once, and only one of them is about the market. The first is whether the market will move in their favor if they wait. The second is whether they can genuinely afford to do this today. The third is whether the change would make their life better, worse, or about the same. Most of the people I have watched lose a year were answering the first question while the second and third decided it.
NOBODY CAN TELL YOU WHEN THE MARKET TURNS, AND THAT INCLUDES ME
There is no bell. Nobody rings one at the top and nobody rings one at the bottom. The people who called the last turn correctly were mostly early, and early costs the same as wrong.
What I can tell you is what is happening on your street and in your price range, and what has actually been selling. That is a smaller claim than a forecast, and it is one I can stand behind. The numbers you read are describing decisions somebody made weeks earlier, so a hot headline and a quiet street can both be true in the same month.
WHAT SELLERS ACTUALLY GET OUT OF WAITING, AND WHAT IT COSTS
Waiting is a decision, not a break from deciding. A seller who waits keeps the house through another season, which is fine if they love living there and expensive if it is sitting empty. They keep paying for it in the ways that never show up as a line item: the insurance, the utilities, the yard, and the repair that picks its own timing.
What waiting does not do is freeze the other half of the transaction. If you are selling in order to buy, the house you would buy next moves in the same market, so a better price on the way out meets a higher price on the way in. I have told people to wait. I have also sat with people who waited and paid for it.
WHAT BUYERS GET IN A CALMER MARKET, AND WHAT THEY GIVE UP
A market without a crowd is a better place to be a buyer than most people realize. You get time to see a second and a third house before you commit. Inspections mean something again, because a seller who is not fielding eight offers will talk about the roof. And the parts of a deal people forget are negotiable become negotiable: repairs, timelines, and what stays with the house.
What you give up is any guarantee about where the payment goes from here. You are buying at today’s terms, not at the terms you hope for in two years, and I will not pretend to know which way they move. If your plan could change in two years, or you have no reserve for the furnace that quits in January, renting is the more sensible answer.
THE COMPARISON I REACH FOR, AND WHERE IT STOPS WORKING
The closest ordinary thing I can think of is the checkout lanes at a grocery store.
You stand in the longest line in the store, watching the next lane move. You switch. The lane you left starts moving immediately, and the new one stalls behind somebody searching for a pen. Everybody has done this, which is why it is the feeling people mean when they talk about timing a market.
Here is where it stops working. In a grocery store both lanes reach the same till, you can see the whole queue, and switching costs you nothing. In a housing market the other lane is a different house with different numbers, the queue is invisible, and the cost of waiting is not ten minutes. It is the house you wanted, and a year of your life.
THE QUESTIONS THAT DECIDE THIS BETTER THAN A FORECAST
So ask these instead of asking anybody to predict the market.
- Money. Not only the down payment. The closing costs, the moving, and a reserve for the thing that always breaks in the first month. If that answer is tight, the timing question is academic.
- Stability. Years, not months. The payment has to survive a job change, a new baby, a parent who needs help, or a return to the office.
- Does it make sense for your life. The school, the street, the commute, the people you want to be near, and whether you want to spend Saturday on yard work.
If you are selling, add one more: what is the next place, and what does the move actually change? A house that is better located and more expensive is a trade, not a loss, and the wrong version is the one nobody priced out in advance.
WHAT I WOULD TELL YOU IF YOU ASKED ME TOMORROW
Most of my job is not predicting anything. It is reading the data that is not obvious online, positioning a home before it goes live rather than three weeks after, spotting the risk you would not have seen on a walkthrough, starting the financing before the offer instead of after, and keeping the decision tied to your plan instead of to this week’s headline.
Some of the most useful conversations I have had ended with both of us agreeing that now was not the time. I would rather tell you that in your kitchen than have you find it out a year later.
If you are further along than this, the selling side is in how selling your home works with me, the buying side is in how buying a home works here, and if the rate is what you are stuck on, the current board is on the mortgage rates page.
Question for you: if you took the market forecast out of the equation entirely, what would your decision look like? Would it change, and by how much?
Adapted from Is Now a Good Time to Buy or Sell? Why Education & Trusted Guidance Matter More Than Ever, originally published by Windermere Signature Properties at windermerecalocal.com.
WHEN YOU ARE READY
Let’s talk about what you want in an area.
Send me the areas you are considering and what matters most to you. I will tell you what each one is actually like, including the parts that argue against it. Nothing is committed by asking.





