One of the most common things I hear from homeowners is this:

“We’ll probably sell once the market improves.”

Reasonable thought.

The problem is that timing property markets is far harder than it sounds. Many owners spend years waiting for the perfect moment, only to find prices have moved far less than expected.

And in many parts of Stonnington, that has largely been the story of the last decade. 

Yes, there have been rises, falls and bursts of momentum, but unless you timed things particularly well, simply sitting tight has often been less rewarding than people imagined.

I’ve wanted to write this piece for a while.

This is not based on CoreLogic charts, Valuer-General spreadsheets, or something I asked ChatGPT to calculate.

It’s based on being in the trenches.

Carla and I have sold over 1,000 houses since 2016, mainly period homes across Stonnington, and tracked thousands more results in that time.

Not apartments.

Not townhouse developments.

Houses.

Victorians. Edwardians. Family homes. Renovated homes. Unrenovated homes. Great streets. Average streets. Premium stock. Problem stock.

And my honest observation is this:

For many Stonnington houses, the last decade has felt a lot flatter than people think.

Yes, there have been swings.

2016 and 2017 were strong.

2018 and 2019 were patchy after the banking Royal Commission and election uncertainty.

2020 and especially 2021 saw a genuine boom. Cheap money, confidence, FOMO, people losing their minds.

Then came rate rises.

2022 to 2024 was more of a reset than a crash.

2025 improved.

And right now, the market feels like it is in another transition phase. 

Buyers are more cautious, confidence is shaky, and global uncertainty plus interest rate settings are clearly part of the conversation.

That said, transitional markets often create excellent opportunities.

Especially for upsizers.

If competition softens on the home you want to buy, the gain there can easily outweigh any softer conditions on the one you are selling.

But when you zoom out and flatten the waves, many houses are worth surprisingly similar money to several years ago.

That statement annoys some people.

But I think it is broadly true.

Of course there are exceptions. 

Some homes have smashed it.

Usually because they were bought well, renovated intelligently, held tightly, or are simply special.

Others have gone nowhere.

Some have gone backwards in real terms once you factor in stamp duty, holding costs, rates, renovations and inflation.

That’s the bit nobody likes talking about at dinner parties.

So, what’s the point of this article?

Not negativity.

Not “don’t sell”.

Quite the opposite.

It’s to challenge the idea that waiting is always the smart move.

Many owners have spent years waiting for a magical price jump that never really came.

Meanwhile they delayed:

– upsizing
– downsizing
– school moves
– less debt
– better streets
– more freedom
– a home that suited them better

Sometimes waiting works.

Sometimes it’s just expensive procrastination.

The bigger truth is this:

Your outcome is often driven less by “the market” and more by presentation, pricing strategy, timing within the season, competition levels, buyer depth, negotiation skill, and what you are buying next.

I’ve seen sellers obsess over getting an extra $80,000 for their home while missing the chance to buy the next property $250,000 cheaper than it would have been in a hotter market.

That’s stepping over dollars to pick up cents.

Markets move.

Life moves faster.

If you bought in 2014 or 2015, you’ve likely done well.

If you bought in the frenzy years, maybe less so.

If you bought in quieter years, probably fine.

But regardless of when you bought, the question today shouldn’t simply be:

“Will prices be higher in two years?”

It should be:

“What move best improves our life, and can we execute it well now?”

That is usually the better question.

Because homes are not just charts and percentages.

They’re where your kids grow up.

Where you host Christmas.

Where you pace around on stressful phone calls.

Where life actually happens.

If the right move is there now, waiting for a headline may not be the smartest play.

Feature Property: 24 Mt Pleasant Grove, Armadale

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