Selling
Selling to retire
Many owners decide to sell when they’re ready to step back. Starting a few years early gives you more choices and usually a better result. Two to five years out, get a value, talk to your accountant about tax, and sort out leases and repairs so buyers see a clean building.
Seller representation
What selling to retire involves
A plain explainer if you’re new to this.
- What it is
Selling a property you’ve held for years
You’re ready to stop managing property or running your business and want to turn the property into cash or income.
- How it works
Sale price and tax
Long-held properties often have large gains and recaptured depreciation. See CRA’s capital gains guide and plan with your accountant before listing.
- Options
Cash, payments over time, or a lease
You can sell outright, take some payments over time, or sell and lease back if the business stays. Each has different tax and risk.
- What I do
Timing and a clean sale
I help set the timing, prepare the documents and find a buyer who can close.
Start two to five years out
That gives you time to clean up the books, extend key leases, reduce how much the business depends on you, and talk to your accountant about structure. The lifetime capital gains exemption, for example, has tests that look back 24 months.
Choose the path
- Sell everything: the building, the business or both.
- Sell the business, keep the building: lease it to the buyer and keep a rental income.
- Family or staff: a transfer to family or a sale to managers, often with a vendor take-back.
- Sell to a third party: a competitor, an individual buyer or an investment group.
Leases add value
A building with a fresh long lease usually sells better than one with a lease about to end. If a major lease ends soon, think about renewing first.
How I help
I look at the property and the business together, lay out the paths and help you choose the timing.
Questions people ask
How early should I start planning to sell before retiring?
Two to five years is a good range. It leaves time to fix the books, extend leases and plan the tax side.
Can I sell my business and keep the building?
Yes. Many owners lease the building to the buyer and keep the rent as retirement income.
Will I pay tax when I sell?
Probably, and the amount depends on structure. Talk to your accountant early.
What should I gather, ask and watch for?
Documents to gather
- Title and property tax notices
- Leases and operating statements
- Mortgage statement and terms, including prepayment penalties
- Wills, partnership or shareholder agreements, if they apply
Questions to ask
- What is the property worth today, roughly?
- What tax does a sale trigger, and can timing help? (ask your accountant)
- What does it cost to break the mortgage?
- Who has to sign, and do they all agree?
Common mistakes
- Waiting until you have to sell
- Making the decision without tax advice
- Not checking who has authority to sign
- Underpricing to sell fast without testing the market
Typical timeline
- NowValue range and tax advice
- Months 1 to 3Decide and prepare
- Marketing to offerOften 1 to 3 months
- Completion30 to 90 days after conditions
Typical ranges. Your lease, lender and the City set the real dates.
Go deeper
If you’re looking for more details
Retirement sale timeline (typical estimates)
- 3 to 5 years out: accountant, structure, lease renewals
- 1 to 2 years out: clean books, hand off duties to staff
- 6 to 12 months out: valuation, prepare documents
- Sale: marketing, offers, conditions and completion
Search
Not quite your situation? Search
Next step
Thinking about retiring?
Tell me what you own and when you’d like to step back. The first conversation is confidential.