Should you sell first or buy first when downsizing?

The fear driving the question

Every downsizer asks the same thing first, and it is rarely about price: what if my home sells and I have nowhere to go, or I find the right condo and my home has not sold? Both fears are legitimate, and the answer is not to pick the risk you prefer. It is to sequence the move so neither fear gets a vote. Banks frame the choice the same way: in a market with more sellers than buyers, a purchase conditional on your sale can work; in a tight market it makes your offer the one sellers skip.

Why selling first usually wins in Durham

Three reasons. First, certainty: you know your exact proceeds before committing to the next home, which sets an honest budget instead of a hopeful one. Second, strength: a firm buyer with no sale condition wins negotiations that a conditional buyer loses. Third, the local market: TRREB’s June 2026 data put Durham at 3.4 months of inventory, the tightest in the GTA, and in a market like that sellers rarely need to accept an offer that depends on someone else’s house selling. When they do accept one, Ontario practice attaches an escape clause, commonly 48 hours: the seller keeps marketing, and if a better offer arrives you either firm up immediately or lose the home anyway. The condition you hoped would protect you becomes a countdown.

Bridging the gap without owning two homes

Selling first does not mean moving twice. The gap between selling and settling has three standard bridges. A long closing, 60 to 90 days or more, negotiated in the sale agreement, buys shopping time while the deal is firm. A leaseback keeps you in your home after closing as the buyer’s tenant for an agreed period, with the arrangement in writing. And where the next purchase closes days or weeks before the sale funds arrive, bridge financing covers the overlap at a known, modest cost, because a firm sale is exactly what bank bridge loans require.

When buying first makes sense anyway

Sometimes the right home shows up early, a bungalow in the exact pocket you wanted, and waiting means losing it. Buying first can work, with honest eyes on what it demands: your sale is now on a deadline, each month of overlap costs thousands in duplicated carrying costs, and without a firm sale agreement the only bridge money available is private lending at a premium. If that is the road, preparation becomes everything, because the faster your home sells at full value, the shorter the exposure. That is where launch condition and timing stop being nice-to-haves. Either way, one team coordinating both transactions is what turns two stressful deals into one planned move.