Why It Feels So Hard and How to Make It Easier
For families who have outgrown their current home, upsizing should feel exciting. A chance to gain breathing room, improve daily routines, and finally have space that works for everyone. But in reality, the moment you start planning to sell your home and buy another at the same time, the stress can hit fast. Coordinating two major moves while juggling kids, work, school schedules, and life is one of the biggest challenges.
The good news? With the right approach, you can take control of the process instead of letting it control you.
The Timing Dilemma: Sell First or Buy First?
This is the question that keeps most families up at night. In 2026’s potentially more balanced GTA market, both paths can work, but each comes with trade‑offs.
Selling first gives you clarity on your budget and avoids carrying two homes at once. It’s the safer financial route, but it may require temporary housing or storage if your next home isn’t ready.
Buying first gives you the comfort of securing the right home for your family, especially if you have specific needs like school districts or bedroom count. But it requires confidence in your current home’s saleability and may involve bridge financing.
There’s no universal answer. The right choice depends on your timeline, your market, and how quickly homes like yours are selling.
Managing the Chaos: What Families Can Do Now
The biggest pain point for upsizers isn’t the move itself, but rather the overlap. Here’s how to make the process smoother:
- Start prepping your current home early. Decluttering, small repairs, and pre‑listing photos can all be done before you even start shopping.
- Know your non‑negotiables. More space is the goal, but clarity on layout, neighbourhood, commute, and school zones keeps you focused.
- Have a plan for the “in‑between.” Whether it’s staying with family, short‑term rentals, or storage pods, having a backup plan removes pressure.
- Lean on professionals. A realtor who coordinates both sides of the move can streamline timing, negotiations, and logistics so you’re not carrying the mental load alone.
- Keep communication tight. When buying and selling overlap, quick decisions matter. Staying responsive helps everything move faster.
Why 2026 Is Actually a Good Year to Upsize
With more inventory on the market and less competition than in the peak years, families have more breathing room to find the right home without rushing. Homes are still selling, but buyers have more leverage, which is a rare combination that makes upsizing more manageable than it’s been in years.
The Bottom Line
Upsizing in 2026 is absolutely doable — even for the busiest families — when you approach it with a clear plan, the right support, and realistic expectations. The process may feel overwhelming at times, but the payoff is worth it: a home that finally fits the way your family lives today.