Evaluating Your Real Estate Portfolio in a Down Market: Sell, Hold or Refinance?
Evaluating Your Real Estate Portfolio in a Down Market
Chapters/timestamps:
00:00 Introduction – How to Evaluate Your Real Estate Portfolio in a Down Market
00:45 Why Looking at Today’s Prices Can Make You Panic (Zoom Out First)
02:00 Who We Are + My $39K to $20M Portfolio Journey
04:30 Why Annual Growth Rates Don’t Tell the Full Story
05:45 How Wealth Is Built: Tenants Paying Down Your Mortgage
07:50 Long-Term Investing Mindset vs Short-Term Market Fear
09:40 50 Years of Toronto Condo Prices Explained (6%+ CAGR)
11:25 Why Today Isn’t the 1990s Market (Historical Perspective)
13:05 Condo Supply Trends: Completions Rising… Then Falling Fast
14:55 Sales Slowing + Population Growing – What This Means
16:10 Future Supply Cliff: Why 2027–2030 Could Shift the Market
17:40 When Supply Drops, Prices Rise (Simple Economics)
18:40 Next 18 Months Forecast – What to Expect Short Term
19:50 Benjamin Tal & Market Recovery Insights
20:30 Your 3 Strategies: Hold, Sell & Rebuy, or Reallocate
21:40 Why I’m Diversifying Into Self-Storage Investments
22:35 Pre-Construction vs Resale – Which Strategy Makes Sense Now
23:45 Don’t Panic Sell – Think Like a Financial Portfolio Manager
24:40 Condo Selling Reality: Why Buyers Have the Power Today
26:45 Houses vs Condos – Two Very Different Markets
29:40 Rental Market Outlook – Will Rents Rise Again?
32:55 Live Q&A – Real Investor Questions Answered
34:20 Mortgage Strategy to Reduce Monthly Losses
36:30 Equity Recovery Timeline – When Could Prices Rebound?
38:20 Retirement Planning & When It Makes Sense to Sell
41:50 Case Study: Negative Cash Flow Property – What I’d Do
46:50 Calgary Market Strategy & Buy-and-Hold Opportunities
48:20 Final Advice – Zoom Out, Trust Fundamentals, Plan Strategically
Should You Sell, Hold, or Refinance?
If you’ve opened your portfolio lately and felt your stomach drop, you’re not alone.
In a down market, it’s easy to look at your real estate at one moment in time and start questioning everything: Should I sell before it gets worse? Should I refinance? Should I hold and hope?
Here’s the truth: checking your portfolio at a single point in time can drive you crazy—because real estate isn’t meant to be judged like a day-traded asset. At RE/MAX Wealth Builders, we’ve helped 1500+ Canadians invest in real estate, and we’ve found the same principle applies over and over:
The biggest mistake investors make in a down market is zooming in too close.
The smartest decisions come from zooming out.
This blog will walk you through how to evaluate your portfolio with a clear, calm framework—so you can decide whether you should sell, hold, refinance, or strategically reallocate.
Step 1: Stop Treating Real Estate Like a Moment-in-Time Decision
When investors panic, I ask a simple question:
If this were your RRSP or stock portfolio… would you sell everything right now?
Almost always, the answer is no.
Because you understand two things about stocks:
Selling during a dip locks in losses
Selling can create tax consequences, and you lose the recovery
Real estate works the same way.
That doesn’t mean you should never sell. I’ve sold properties from my own portfolio recently. But selling should be a strategic decision, not a reaction.
So the first step in evaluating your portfolio is this:
✅ Separate market fear from real financial need.
✅ Understand what you own, why you own it, and what your time horizon is.
Step 2: Zoom Out to the Real Wealth Equation
I’ve built a real estate portfolio from a $39,000 deposit into roughly a $20 million portfolio.
And I don’t say that to impress anyone. I say it because it proves something important:
Wealth in real estate isn’t built in the “perfect years.” It’s built over time.
When you zoom out and look at real estate over decades, the long-term trend becomes clear:
In 1974, condos were roughly $25,000
Over a 50-year period, the compound annual growth rate (CAGR) for condo prices is approximately 6.1% annually
And remember: real estate is typically purchased with leverage. If you put 20% down, you’re not earning growth on the full purchase price out of pocket—you’re earning it on an asset much larger than your initial investment.
That’s why the real wealth equation in real estate looks like this:
Long-term appreciation + leverage + principal paydown (by tenants) = wealth
Even in markets where some properties are cash flow negative today, time and amortization still matter.
Step 3: Understand What’s Happening in the Condo Market Cycle
Right now, yes—Toronto condo prices are down from peak. Many investors are also facing:
Softer rents in certain unit types
More competition from listings
Higher carrying costs than expected
This is where people make the mistake of assuming:
“If it’s bad today, it will be bad forever.”
But real estate moves in cycles, and the key is understanding where we are in the cycle.
Prices by decade show volatility—but long-term upward movement
When we look at historical decade-by-decade growth:
1970s: strong growth
1980s: moderate growth
1990s: weak decade (but still positive overall)
2000s: strong growth
2010s: very strong growth
2020–2024: still positive overall, despite volatility
Even people who lived through the 1990s (which was a notoriously rough market) will tell you:
Today is a bad market—but it’s not “1990s bad.”
The bigger takeaway is this:
✅ If you zoom in to today, it looks terrible.
✅ If you zoom out to decades, it looks like a normal cycle.
Step 4: The Supply Problem Nobody Can Ignore (and Why It Matters)
Here’s where the conversation becomes less emotional and more economic.
Over the last 5 years, the GTA has averaged roughly 30,000 condo completions per year.
But the future supply pipeline is projected to drop sharply:
~20,000 completions in 2026
~10,000 in 2027
~5,000 in 2028–2029
and potentially near-zero completion levels by 2030 in some forecasts
At the same time, population growth continues. The GTA population trajectory has grown substantially since 2010, and estimates still point toward major long-term growth by 2030.
So when you combine:
📈 Population growth
📉 Future condo completions falling
⏳ A multi-year construction timeline (you can’t “turn on supply” instantly)
You get one clear economic reality:
When supply tightens, prices rise.
That doesn’t mean prices rise next month. But it’s why long-term investors pay attention to fundamentals, not headlines.
Step 5: Be Honest About the Next 18 Months
Here’s the responsible part of this conversation:
The next 18 months may still be difficult.
We’re still working through a buyer’s market dynamic in condos, and it wouldn’t be surprising to see continued weakness before recovery.
That’s why your portfolio evaluation needs to include:
Can you hold through a slow period?
What will your cash flow look like at renewal?
What happens when rates continue to trend down?
Because the good news is: your portfolio doesn’t stay frozen at today’s interest rates.
Step 6: Don’t Judge Cash Flow Without Looking at Your Mortgage Structure
A lot of investors say:
“I’m losing $800 a month.”
But the real question is: what does that $800 include?
Sometimes, “loss” includes principal paydown. In other words: you’re not losing money—you’re paying your own mortgage faster (which increases your equity).
Also, many investors are in mortgages signed in 2022–2023 at much higher rates than what we may see at renewal.
So instead of evaluating cash flow only in today’s frame, ask:
✅ What does this property look like at renewal in 2026?
✅ What does cash flow look like when rates drop 2%?
✅ Can refinancing or switching terms reduce the monthly bleed?
Sometimes, one of the simplest strategies is just restructuring the mortgage so payments reflect current rates—especially for investors stuck in payment structures that haven’t adjusted downward.
Step 7: Your Three Real Options in a Down Market
Once you zoom out and look at fundamentals, your choices become clear. In most situations, investors fall into one of three paths:
1) Hold until recovery
If you have the ability to hold, and your long-term strategy is wealth-building, this is often the simplest move.
Recovery is unlikely to be immediate—but looking out to 2027–2028, the supply-demand story changes dramatically.
2) Sell now and buy the dip later
Some investors with strong equity positions are cashing out intentionally—planning to re-enter when prices are lower, likely in the next cycle’s bottoming period.
This requires:
discipline
timing
and a clear plan to re-enter (not just “wait and see forever”)
3) Reallocate into different asset classes
If you’re heavily concentrated (and dealing with multiple mortgages, appraisals, and tenant stress), diversification can make sense.
Personally, I’ve been diversifying into areas like self-storage development, because it reduces three major stress points:
fewer mortgage headaches
fewer appraisal issues
fewer tenant challenges
That doesn’t mean condos are “bad.” It means your strategy should match your stage of life and stress tolerance.
Step 8: The Real Question Isn’t “What Is My Condo Worth Today?”
The most helpful question isn’t:
“What’s my condo worth right now?”
It’s:
✅ What will this asset look like in 2028–2030?
✅ What is my renewal risk and interest-rate trajectory?
✅ Do I need liquidity—or do I just need peace of mind?
✅ What’s my plan if I sell—where does the money go?
Because remember:
You only lose in real estate if you sell.
If you don’t sell, your investment is still an asset working in the background—being paid down over time while markets cycle.
If You’re Feeling Stressed, Book a Call (Because Strategy Beats Panic)
If you’re unsure whether you should sell, hold, refinance, or reallocate, you don’t need hot takes—you need a portfolio review.
At RE/MAX Wealth Builders, we’ll help you:
understand the true market value of your holdings
model your cash flow today vs. at renewal
identify the best move based on your goals and lifestyle
build a plan that feels rational, not reactive
The goal is never “never sell.”
The goal is: if you sell, it’s educated. If you hold, it’s confident. If you refinance, it’s strategic.
Book a call with Alex - click here
Alexander J. Wilson
#2 Individual RE/MAX Agent for Closed Sales in Canada 2024
#1 Individual RE/MAX Agent for Closed Sales in Canada 2022
Member of RE/MAX Circle of Legends
Broker Owner
RE/MAX Wealth Builders Real Estate
Email: alex@remaxwealth.com
Office: (416) 652-5000
Mobile: (416) 996-5181
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