Your Decision Checklist: Which Strategy Is Actually Yours?

   
Part 1: Sell First or Buy First? Part 2: You Sold. Now What? Part 3: The Moves Nobody Tells You About Part 4: Your Decision Checklist

This is your decision framework, the same one we walk through with every client in their first real conversation with us. It takes about 20 minutes. It replaces months of second guessing. And it has, on at least three documented occasions, saved a marriage.

Step 1

Know Your Numbers Before Anything Else

Three figures. Without these, everything else is guesswork. Most people skip this step and pay for it later. Do not be most people.
What You Need How to Get It
Your home's current market value Ask us for a Comparative Market Analysis (CMA). Free, no obligation, no gotcha.
Your net equity after closing costs Market value minus your mortgage, minus approximately 4 to 5% for legal fees and commission.
What you can qualify for on the buy side Talk to your mortgage broker before you list. This tells you what bridge or overlap scenarios look like.

Step 2

Honest Gap Tolerance Questions

This is less about finances and more about knowing yourself. Answer honestly. There are no wrong answers, only answers that point you in the right direction.
  • Could you comfortably live somewhere temporarily for 30 to 90 days? YES Selling first with a gap is workable. NO Prioritize rent-back, co-ordinated closings, or bridge financing.
  • Are you moving with pets, elderly parents, or young children? YES Moving twice is significantly harder. Worth paying for a one-move strategy.
  • Will financial uncertainty affect your daily life in a meaningful way? YES Sell first. Certainty is worth more than flexibility for you. NO You have more options, including buying first.

Step 3

What Are You Buying Into?

This question changes everything, and most people skip it entirely. The type of property and neighbourhood you are targeting should directly shape your strategy.
  • Buying a condo in Humber Bay Shores, Queensway, or Port Credit? Inventory exists. Sell first, take your time, you'll find the right unit.
  • Buying detached on a specific street in The Kingsway or Mimico Beach? Inventory is thin. Waiting post-sale might mean losing the opportunity. Consider buying first with a bridge loan.
  • Downsizing significantly? Condos are far more available than detached homes. Selling first works well here.
  • Staying in the same neighbourhood? Co-ordinated closings become much easier to negotiate. Lean on that option.
"The number of times I've heard 'we want something on that specific street' — that's a legitimate reason to move differently. But 'a nice 2-bedroom in a good Etobicoke building'? Sell first. We'll find it for you." — Kathy Gordon

Step 4

Match Your Profile to a Strategy

Use the table below to find the path that fits your equity position, timeline, and situation. This is a starting point for a conversation, not a final answer.
Your Equity Your Situation Recommended Path
$600K+ No or low mortgage, flexible timeline
$300K to $600K Small mortgage, moderate timeline
Under $300K Significant mortgage remaining
Any Specific rare property in sight
Any Estate or probate property
Any Kids, pets, or parents in tow

Your Pre-Move Checklist

  • Get a current market valuation, know your equity before anything else.
  • Talk to your mortgage broker about carrying costs and bridge scenarios.
  • Apply for a HELOC now if your equity allows it, before you list.
  • Decide on your gap plan: rent-back, short-term rental, or family (warn them).
  • Identify your top 3 to 5 target properties or buildings on the purchase side.
  • Book a strategy conversation with your agent before you do anything else.

The Bottom Line

A Plan Built for Your Circumstances

The sell-and-buy transition is emotionally loaded in a way that is completely underestimated. You are not just moving property, you are moving a chapter of your life. That deserves a plan built for your circumstances, not someone else's. What we have learned from doing this for over 50 years: when you have a clear plan, it becomes logistics. Good logistics, handled by people who care. The anxiety goes from constant to occasional. The decisions feel less like gambles and more like choices. That is what we want for you.
"And if you have questions these posts didn't answer, call us. Not a form. Not a chatbot. Us." — Lauren Gordon
 

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