Thinking About Upsizing? You May Be Sitting on a $50,000-$100,000+ Opportunity Without Realizing It

Thinking About Upsizing? This May Be One of the Best Opportunities We’ve Seen in Years

When most people think about moving to a larger home, they focus on one question:


“What will my house sell for?” While that’s certainly important, experienced real estate professionals know there’s another question that can be even more important:


“What am I buying?”


Right now, many homeowners living in freehold townhomes and entry-level detached homes may be in a surprisingly advantageous position if they’re considering a move to a larger property.


The Market Isn’t Moving Equally

One of the biggest mistakes people make is assuming all homes rise and fall in value at the same rate. In reality, different price segments often perform very differently.

Over the past several years, homes in the approximately $700,000 to $850,000 range have remained relatively insulated compared to condominiums on one end of the spectrum and higher-priced homes on the other. These properties continue to attract strong buyer demand because they often represent the most attainable freehold ownership option for many families.

When priced correctly, they continue to generate significant interest.


The Opportunity Exists in the Gap

Meanwhile, many homes in the $1 million to $1.5 million price range have experienced greater challenges.


In many areas, they’ve seen:

• Larger price corrections
• Increased inventory levels
• Longer days on market
• Greater competition among sellers
• More room for buyer negotiation


Why does this matter? Because when you’re upsizing, the goal isn’t simply to maximize the sale price of your current home. The goal is to maximize the difference between what you’re selling and what you’re buying.


A Simple Example

Let’s assume: Your current home is worth $800,000. A larger home you want to purchase was previously worth $1.5 million.


If both homes decline by 10%:


Your home decreases by approximately $80,000. The larger home decreases by approximately $150,000. That’s a $70,000 difference. Even though both homes declined by the same percentage, the higher-priced home experienced a much larger dollar-value reduction. This can create a unique advantage for move-up buyers.


In some situations, homeowners can effectively purchase more house for less money than would have been possible during a stronger seller’s market.


Inventory Is Creating Additional Opportunities


Another important factor is inventory. Higher-priced homes generally have more competition right now.


More listings often mean:

✓ More options to choose from
✓ More negotiating leverage
✓ Better conditions for buyers
✓ Less pressure to make rushed decisions


When supply increases and demand softens, buyers gain leverage. For homeowners looking to move up, this can create opportunities that simply don’t exist in tighter markets.


Looking Beyond the Headlines


The reality is that successful real estate decisions aren’t made by looking at one number. They’re made by understanding the complete picture.


Market sentiment.

Inventory levels.

Supply and demand.

Buyer behaviour.

Negotiating conditions.

Price segment performance.

These factors all matter.


That’s why two homeowners can look at the exact same market statistics and reach completely different conclusions. One sees uncertainty. The other sees opportunity.


Is Upsizing Right for You?

Every situation is unique. Your equity position, mortgage structure, timing, and long-term goals all play an important role. However, for many homeowners currently living in freehold townhomes or entry-level detached homes, today’s market conditions may present a rare opportunity to move into a larger home while the gap between price segments remains favourable.

The key is understanding your numbers and having a clear strategy before making any decisions.


Let’s Build Your Plan


If you’ve been thinking about upsizing but aren’t sure whether the timing makes sense, we’d be happy to help. Our team can provide:


• A detailed evaluation of your current home
• An analysis of your move-up options
• Current market insight specific to your neighbourhood
• A customized strategy designed around your goals

The best opportunities often aren’t obvious at first glance.


Sometimes they’re found by looking at the market from a different perspective.


Reach out today and let’s explore whether this unique market window could work to your advantage.


📞 Connect with DiLoreto & Co.

🏡  Get a professional evaluation of your home



By Krissie Dwyer April 17, 2026
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