How to Sell a Tenanted Property in 2026

Recorded: December 2025
Guest:️ Tim Hong, Property Manager specializing in selling and managing tenant-occupied properties.
Host: Erwin Szeto, The Truth About Real Estate Investing for Canadians Podcast

Selling an investment property in Ontario in 2026 is not the same game it was in 2021.

If you’re an investor in markets like Hamilton, Kitchener–Waterloo, or the GTA, you’re facing more listings, tougher financing, and smarter buyers. At the same time, interest rates are still high enough to squeeze cash flow, and the Landlord and Tenant Board remains a risk you want to avoid at all costs.

In a recent episode of The Truth About Real Estate Investing for Canadians, I sat down with veteran investor, realtor, and property manager Tim Hong to talk about exactly what’s happening on the ground — and what smart investors are doing instead of panicking.

Inventory Is Up 50–60%… But Prices Are Range-Bound

Tim started by pulling fresh stats from his core markets:

Kitchener–Waterloo: active listings are up from about 810 in November 2023 to roughly 1,296 today — a 60% jump.

Hamilton: inventory is up from ~1,410 to 2,078 active listings, a bit more than a 50% increase.

That’s a huge shift in supply, yet prices haven’t completely collapsed. From the February 2022 peak, we’re still roughly 20–30% down, but for the last three years prices have mostly been range-bound, bouncing up and down within a band.

The takeaway:

If you’re listing your property now, understand you’re competing in a crowded marketplace.

Buyers have time and options. Conditions are back. So are offers conditional on the sale of the buyer’s home.

Power-of-Sale and Estate Sales Are Setting the Bar

When I pulled comparables recently, I saw more power-of-sale and bank-owned listings than at any time since I became a realtor in 2010. I also saw a bank-owned Hamilton Mountain bungalow duplex that sold for around $1.2M at the peak get resold for roughly $720,000 after the bank took it back.

That’s a 40%+ haircut.

These types of listings — bank sales and estate sales — are often:

Aggressively priced to clear quickly.

Heavily influencing buyers’ expectations on what a “deal” looks like.

If you’re a regular investor trying to sell a tenanted duplex, you’re competing against those numbers, whether you like it or not.

Why Single-Family Homes Sell Faster Than Duplexes Right Now

Tim sees a big difference between “obvious rental properties” and end-user homes:

Legal duplexes, triplexes, and vacant student rentals:

Investors are cautious.

Financing is tighter and interest rates are higher.

Offers are often below what sellers want.

Single-family homes for end users:

Bigger buyer pool.

Still seeing healthy activity and occasional multiple offers, depending on location and price.

Investors have no sense of urgency right now. They’ll buy only if the numbers are compelling. That means if your exit strategy relies on another investor paying top dollar, you may need to adjust your expectations — or your strategy.

Plan A vs Plan B: Sell or Re-Rent?

For many of Tim’s clients, the starting plan was:

Tenant leaves.
Touch up the property.
List it for sale.

In several cases, the market response was underwhelming: little activity, weak offers, or no offers at all.

At that point, Tim sits down with the investor and runs the numbers on Plan B:

What can this property realistically rent for with a proper tenant-screening process?

What does cash flow look like at today’s interest rate?

Are you willing to hold for another 3–5 years?

Often, the investor decides that re-renting is the better financial move.

In one case, an investor was set on selling a property with long-term tenants paying below-market rent. Once they saw the projected sale price and tax implications, they weren’t excited.

Tim approached the tenants directly, explained the situation, and negotiated a new lease at a higher rent that was still below market. The result?

The investor kept the property.

Cash flow increased by about $560 per month.

The tenants gained security and avoided the uncertainty of a new owner.

That’s the power of creative negotiation and treating selling as one option, not the only option.

The Resilience of University Student Rentals

While many asset classes are feeling pain, university-area student rentals have quietly been one of the most resilient strategies over the last decade.

Why?

Enrollment tends to increase during economic downturns.

Universities have more stable, diversified demand than some private colleges that leaned heavily on international students.

Student rentals naturally build in tenant turnover every 2–3 years, letting landlords reset rents to market regularly.

College-focused markets tied to international enrollment — think Conestoga and similar schools — have seen dramatic drops and oversupply. But university zones around schools like Waterloo, Laurier, McMaster, and others are still seeing strong demand from quality students who want clean, well-managed housing.

Bill 60 and the Future of Selling Tenanted Properties

We also talked about Bill 60 and what it could mean for investors:

Shorter timelines for non-payment of rent (N4 going from 14 days to 7).

Requirements for tenants to pay 50% of outstanding rent into the system if they want to raise maintenance issues at a hearing.

Possible relief from compensation requirements if you give 120 days’ notice to a tenant for a buyer’s own use.

None of this is a magic fix. But it may tilt the playing field slightly back towards responsible landlords who follow the rules.

The safer strategy remains the same: avoid the Landlord and Tenant Board completely by screening tenants properly, communicating clearly, and handling issues early.

Tenant Screening: Why Tim Hasn’t Been to the LTB in Two Years

Tim’s property management company hasn’t had to attend the LTB in two years. His process is simple but strict:

Use SingleKey for credit and application processing.

Use OpenRoom to check for existing court orders.

Verify employment, income, and current landlord through independent searches.

Watch how tenants communicate and follow instructions.

If someone no-shows a viewing without notice, asks for four parking spots on a property with one, or can’t be bothered to read the ad, they’re disqualified.

Is it harsh? Maybe.

Is it effective? Definitely.

If you want high-quality, long-term tenants who pay on time and treat your property like a home, you need to raise the bar.

Should You Buy Vacant or Tenanted Right Now?

Given longer vacancy times for new listings and the sheer number of options tenants have, Tim makes a point many investors miss:

If you’re buying locally and want a relatively hands-off experience, consider buying a property with a good, paying tenant in place at a fair rent — as long as you can verify their history and lease.

If you buy vacant, be prepared for two months (or more) of vacancy, plus screening, showings, and uncertainty.

In today’s market, time is money, and two months of lost rent plus your own time and stress can eat up a lot of the “deal” you thought you were getting.

🎧 Listen to the full episode here

Final Thoughts: Hold, Sell, or Pivot?

If you own investment real estate in Ontario right now, you don’t need fear. You need a clear decision-making framework:

Check your numbers honestly. Can you carry the property for another 3–5 years if you re-rent at realistic market rents?

Know your asset. Is it a quality property in a solid location, or is it a weak property that only looked good in a spreadsheet?

Understand your buyer. Are you selling to an end user or another investor? The strategy, staging, and pricing are different.

Have a Plan B. If the right offer doesn’t come, be ready to re-rent, renegotiate with tenants, or refinance instead of selling at a painful discount.

Save the date

How to Sell Investment Property for Maximum ROI. Online-Only Live Masterclass | Tuesday, January 13th · 8:00 PM EST

If you’re thinking about selling in 2026, join us on January 13th at 8 p.m. Eastern for our free IWIN training: “How to Sell an Investment Property for Maximum ROI.”

REGISTER HERE

We’ll walk through:

Real examples of deals that sold vs. deals that pivoted to Plan B.

How to price properly in a market full of bank sales and estate sales.

Tenant strategies that make your property more attractive — or at least not a liability — when you hit MLS.

In this market, you don’t have to get crushed. You just have to be smarter than the average seller.

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Early-bird registration is now open — save 40% when you secure your spot early. Seats for the in-person experience are limited and always sell out fast.

Discover the frameworks, tax strategies, and legacy tools top performers use to stay ahead — no matter the market.

Top 10 FAQs About Selling Investment Properties in Ontario (2026 Edition)

Q: How has the Ontario real estate market changed for investors going into 2026?

A: Inventory in markets like Hamilton and Kitchener–Waterloo is up 50–60% compared to 2023, while prices are roughly 20–30% below the 2022 peak and range-bound, so investors face more competition when selling.

Q: Is 2026 a good time to sell an investment property in Ontario?

A: It can be, if you’ve owned for several years and price realistically against bank sales, estate sales, and higher inventory, but many investors are better off re-renting and waiting out the market if they don’t need to sell.

Q: What’s the biggest mistake investors make when selling rental properties in Ontario?

A: Hiring a non-investor realtor and ignoring tenant issues; when the property doesn’t sell, they pivot to Plan B with a poorly screened tenant and can end up in Landlord and Tenant Board nightmares.

Q: Are student rentals still a good investment strategy for Canadian investors?

A: University student rentals near major Ontario campuses remain one of the most resilient cash-flow strategies, thanks to strong enrollment and regular tenant turnover, whereas college-heavy markets reliant on international students have struggled.

Q: How long does it take to find a good tenant in the 2026 Ontario rental market?

A: In many areas it now takes 6–8 weeks or more to find a high-quality tenant for single-family homes, duplexes, and basement units, so investors should budget for at least two months of vacancy.

Q: What are the best tenant screening tools for Ontario landlords?

A: Many professional property managers use SingleKey for credit and application processing and OpenRoom to check for existing court orders, combined with manual checks of income, landlord references, and online searches.

Q: How will Bill 60 impact landlords and selling investment properties?

A: Bill 60 proposes shorter timelines for non-payment, potential changes to compensation when buyers move in, and rules requiring tenants to pay a portion of rent owed before raising maintenance complaints, which slightly improves the environment for responsible landlords.

Q: Should I buy a vacant rental property or one with tenants in place?

A: In today’s market, buying a property with a strong, paying tenant at near-market rent can be safer because buying vacant often means at least two months of vacancy and extra leasing risk.

Q: What types of rental units are most in demand in Ontario right now?

A: Larger, brighter units—especially above grade, with multiple parking spots and family-friendly layouts—are renting faster than small micro-condos or cramped basement apartments.

Q: How can Canadian investors protect their cash flow until interest rates drop?

A: Focus on tenant quality over speed, consider rent renegotiations with below-market tenants, and be willing to pivot from selling to re-renting if offers don’t match your long-term goals.

📜 Full Transcript

The full, cleaned transcript of my conversation with Tim Hong is available here for anyone who wants to dive deeper.

To Listen:

On iTunes: https://podcasts.apple.com/ca/podcast/apartments-vs-business-income-how-real-estate-investing/id1100488294?i=1000733146751

On Spotify: https://open.spotify.com/episode/0g5Jt74Qff54WifcfEU6FH?si=3554156498454d05

Amazon Music: https://music.amazon.ca/podcasts/40fe627d-dec7-4f5d-b7e5-90a550fffe46/episodes/c50ae533-1e20-4bf2-80d9-82ddb8d70b7d/the-truth-about-real-estate-investing-for-canadians-how-to-sell-a-tenanted-property-in-2026-what-investors-need-to-know-now

Audible: https://www.audible.ca/pd/B0G53GJWGW?source_code=ASSGB149080119000H&share_location=pdp

YouTube: https://youtu.be/-G3MkQjEH4Y

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Disclaimer

As a committed advocate for transparent and responsible investing, I want to disclose that I am an Advisor to SHARE SFR (Single Family Rental). I hold equity in the company and earn referral commissions from clients I refer.

My endorsement of their model—focusing on positive cash flow and direct ownership—is based on personal experience and belief. Still, every investor should do their own due diligence.