Drop Anchor: Rosemary Beach, Florida
Recalibrate the Noise
Rosemary Beach, Time Frames, and What You Think You Know
If you read this staring point post, you already stepped outside the presentism mindset. If not, go back and read it. This builds directly on that conversation.
Gayle was among the original owners on Round Road in Rosemary Beach, watching it come out of the ground beginning in 1996. She and I have both tracked pricing here for as much of that time as we reasonably could — and we still do today.
That gives you perspective. Not opinion. Perspective.
So let me ask you something.
What do you think the average annual rate of appreciation has been in Rosemary Beach since 1999?
It’s 6.6%.
That’s not a boom story. That’s a long arc.
Now let’s narrow the lens.
From 1999 to 2008, what do you think it was?
4.4%.
From 2009 to 2018?
3.8%.
From 2019 to 2025?
Roughly 6%.
From 2022 to 2025?
–1.8%.
Yep. Negative.
Same market.
Same place.
Same buyer types.
So now what?
Is This a Random Walk?
I wouldn’t say that at all.
There is clearly a modest upward bias over long measuring periods — but it only reveals itself if you’re willing to step back far enough to see it.
Still, some people won’t think things are okay.
If you believed 2022 was a great time to buy in Rosemary Beach, so far the data says you’re not standing on particularly solid ground.
That’s not an indictment.
It’s just where we are.
Where we are now.
But Here’s What’s Interesting
If you have no compelling goal, no dream, no reason to buy a home for your family, the numbers above will stop you in your tracks.
If you want to build sandcastles with your grandbabies on the beach, you’ll find a way to take the steps necessary to do that.
Too many realtors — and too many buyers — hide behind ROI and “great investment” language. They see no path forward. Others look at the same reality and understand exactly what this is about: time with family and the nature of what we actually get on this earth.
They’ve reached a kind of freedom.
And if you evaluate the numbers above against pure investments, you already know the answer. You can do as well, if not measurably better, elsewhere.
So what is it that we are really doing here on 30A — in Rosemary, Seaside, WaterColor, and WaterSound?
Time Frames and Narratives
Realtors — and buyers and sellers — tend to select time frames that suit the narrative they want to tell.
Have I really done that here?
If I wanted to argue the market is falling, I could focus exclusively on the last four years. I could also conveniently pull 2004 to 2008 as a comparison set.
How do you think that comes out?
Let that rest with you for a moment.
2004 to 2008 — how did the market do?
Did you avoid it then?
Or is that period now something you reach for to justify not acting today?
What are you anchored on that makes you move — or freezes you in your tracks?
Now, if you’re anchored on “down 20%” because that’s what you remember from that period — just like now — maybe you’re right.
Or maybe you’re missing how a discretionary, secondary vacation home market like Rosemary Beach actually behaves.
Let that sink in.
Down 20%.
Think about that.
What’s the Point?
With the charts and graphs in the first story, and seeing similar patterns show up in WaterColor as well, I wanted to tell the same story a few different ways.
This Rosemary Beach version simply slices time and lets the long arc speak.
Perhaps it supports your narrative to buy. Over a very long time frame, pricing here may appreciate around 6.6% per year. Not bad.
Or perhaps you want the data that tells you not to buy. Over the last four years, real value here has declined.
If you want the data and want to walk through it, just leave me a message. I can slice and dice it any way you want.
But let me ask you one more question.
A Simple Question
If I asked you about 2004 to 2008, and in the asking quietly revealed one of our core negotiating strategies — if you can see it — and I said:
Do you think Rosemary Beach pricing was down 35% during that period,
or do you think it was down 50%?
What would you say?
The Point Is…
Very few people operate on more than near-term facts. Sometimes they don’t even need facts — mere suggestions are enough.
For some, near-term means 2023 versus 2022.
For others, it’s a Wall Street Journal article from last week.
It might be a YouTube video predicting collapse somewhere else.
It might be a conversation with a local agent having a slow year.
Whatever it is, that becomes belief.
And belief becomes anchor.
It becomes the point of reference.
Buy Your Straw Hats in the Winter
I have a few phrases I come back to over time that describe how I think about markets and decisions.
One of them is simple:
Buy your straw hats in the winter.
Easy enough when we’re talking about actual hats and real climate winters.
Much harder when we’re talking about abstract ideas — like when to buy a home in Rosemary Beach.
My real version is more like this:
Buy your straw hats in the winter — and learn to recognize when it’s winter.
In the abstract, most people fail because they cannot see winter.
Because the answer to the 35% or 50% question — the one you were absolutely certain was 50%, the one you would have bet the farm on — was…
…almost no change.
From 2004 to 2008, pricing in Rosemary Beach declined only modestly.
In the aggregate, about 3.1%.
At this point, many of you are thinking one thing:
There is no way that’s true.
This guy is wrong.
I lived through that.
Good. That reaction matters.
Because yes — there were painful stretches inside that window.
From 2005 to 2007, prices in Rosemary Beach declined roughly 30.5%.
That was real.
That hurt.
And that’s what most people remember.
But that was not the question.
That was not the slice.
And that is exactly the point.
The anchoring effect is powerful. Once a number takes hold — 30%, 35%, 50% — it becomes the reference point for everything that follows. You stop asking new questions. You stop examining different frames. You defend the anchor.
That’s why anchoring is such an effective negotiation tool when used deliberately.
It’s also why it’s dangerous if you don’t recognize it — because you can be anchored into a belief that no longer applies, or never did in the way you think.
If we were talking 2005 to 2007, then yes — that was a tough couple of years.
But we weren’t.
We were talking 2004 to 2008.
And over that full period, Rosemary Beach pricing changed very little.
If you didn’t see that coming, it doesn’t mean you’re wrong.
It means you were anchored.
So remember what this is really about.
Buying straw hats in the winter only works if you’re honest about whether it’s actually winter — and why you’re buying a hat at all.