Selling & Buying Guide

Downsizing in Newmarket &
York Region in 2026

A Complete Guide for Empty Nesters Ready for Their Next Chapter

By Lee Lander July 31, 2026 8 min read
A well-maintained bungalow with a pink front door in a mature Newmarket neighbourhood on a sunny summer afternoon

Newmarket — York Region

If the family home no longer fits your life, you're not alone. I talk to downsizers every week — couples whose kids have launched, widows and widowers ready for less upkeep, empty nesters who want to travel more and mow less. And the first thing I tell every single one of them is this: downsizing is not a step backward. It's a strategic move toward the lifestyle you've earned.

After 19 years in real estate and over 700+ homes sold across York Region, Simcoe County, and Durham Region, I can tell you that the best downsizing opportunities in 2026 are in places like Newmarket, East Gwillimbury, and Aurora. These communities give you everything you loved about raising a family in York Region — the parks, the neighbours, the sense of community — with options that suit a different chapter of life.

Why This Market Works in Your Favour

Here's something most people don't realize until they run the numbers: the gap between what your family home is worth and what a smaller, lower-maintenance property costs is wider than it's been in years. In Newmarket, the median detached home price sits around $1.085 million, while the average condo sells for roughly $519,000. That's over half a million dollars in equity you can unlock.

For many downsizers, that equity means more than just cash in the bank. It means freedom. A paid-off smaller home. Money to travel, support adult children, or invest for retirement. The York Region market has softened from its 2022 peaks — detached home prices are down about 30 percent from the top — but if you bought your family home ten, fifteen, or twenty years ago, you are still sitting on substantial gains. The key is making sure you capture them before you need to move.

"I've had downsizers tell me they were nervous about selling because they didn't think they could find the right place to move into. That's the part that keeps people stuck. But when we sat down and mapped out exactly what they wanted — one-level living, walkable to shops, no maintenance headaches — and we found it. Every time. You just need someone who knows the inventory and can move fast."

— Lee Lander

What Downsizers Are Buying in 2026

The "downsize" doesn't mean the same thing to everyone. Here's what I'm actually seeing my clients choose this year:

Bungalows — The Gold Standard

A single-storey home with no stairs to worry about, a manageable yard, and a layout that works for aging in place. That's the dream for most downsizers, and it's the hardest thing to find. Bungalows are in extreme demand across York Region because builders haven't been putting them up in any meaningful numbers for years. Glenway Estate in Newmarket is a standout — it offers bungalows on generous 50-foot lots in an established, mature pocket with tree-lined streets and a strong sense of community. When a well-priced bungalow comes to market there, it typically sells quickly to a downsizer who's been waiting months for the right one.

Condos and Condo-Townhomes

For downsizers who want truly lock-and-leave living — no shovelling, no lawn care, no roof to worry about — condos and condo-townhomes are the answer. Newmarket's condo market is honestly one of York Region's best value stories right now. Buildings like the Specialty Lofts at 543 Timothy Street and the Davis Residences offer larger two-bedroom units with walkability to shops, restaurants, and Upper Canada Mall. If you're coming from a 3,000-square-foot detached home, don't worry — I've helped downsizers find condos that feel spacious and well-designed. The key is layout, natural light, and the right building amenities.

Townhomes with Lower Maintenance

Somewhere between a bungalow and a condo sits the condo-townhome — a stacked or freehold townhome where the association handles exterior maintenance but you still have your own front door, a small private outdoor space, and more square footage than a condo. Glenway Estate also has townhome and condo-townhome options in its western section that are worth a look. These are popular with downsizers who aren't ready for condo living but don't want to maintain a full detached property either.

A charming bungalow on a tree-lined street in Newmarket with a pink-accented for-sale sign in the front yard during golden hour
The right bungalow in the right neighbourhood — this is what downsizers are searching for in Newmarket.

The #1 Question: Do I Sell First or Buy First?

This is the question I hear most often, and the honest answer is: it depends on your situation. But here's how I break it down with my clients.

If you need the equity from your current home to buy the next one, you almost always want to sell first. That gives you a firm number to work with, removes the condition on your offer, and makes you a much stronger buyer. The trade-off is that you might need temporary housing or a short-term rental between homes. That sounds stressful, but I've coordinated this move for dozens of clients and it's smoother than people imagine when you have a plan.

If you have the flexibility to buy before selling — maybe you have savings, a HELOC, or family help — buying first lets you take your time finding exactly the right place. Then you sell your current home once you're already settled. This is less common, but it's the lowest-stress path if you can swing it financially.

The bridge option — sometimes we structure a longer closing on the sale (60 or 90 days) to give you time to find your next home without rushing. Or we negotiate a rent-back so you can stay in your home for a month or two after closing while you look. There are creative solutions to almost every situation. Don't let the "sell first or buy first" question paralyze you.

Where to Downsize in York Region

If you're selling a family home in York Region and looking for your next place, here's a quick neighbourhood cheat sheet based on what my downsizing clients are choosing:

What About the Stuff?

I'd be remiss not to mention this, because it's the part nobody talks about. Downsizing means dealing with decades of accumulated belongings — the kids' childhood art projects, the basement full of hockey equipment, the dining room china you've used twice. It's emotional, and it's overwhelming.

Here's what I tell my clients: give yourself time. Start six months before you plan to list, not six weeks. Go room by room. Keep what genuinely matters, donate or sell what doesn't, and let the rest go. I can recommend estate sale organizers, donation pickup services, and moving coordinators who specialize in downsizing moves. And honestly, most people tell me that once they start letting go, it feels liberating — not sad. Lighter. Like you're clearing space for what comes next.

When to Start the Conversation

The best time to start planning your downsizing move is before you feel urgent about it. If you can look at the calendar and say, "I think I'll be ready to move next spring" — that's the perfect time to call me. We can walk through your numbers, talk about what kind of property you're looking for, and build a timeline that takes the pressure off.

I've been doing this for 19 years. I've helped over a thousand families buy and sell homes across York Region, Simcoe County, and Durham Region. I know the bungalow inventory before it hits the market. I know which condo buildings have great boards and which ones to avoid. And I know how to coordinate a sale and purchase so you're never sleeping on a friend's couch wondering when your next home will close.

Downsizing is a big decision. But with the right plan and someone who's done it a time or two — or a hundred times — it doesn't have to be a stressful one.

Lee Lander

Thinking about downsizing and not sure where to start? I'd love to walk through the numbers with you.

Let's Talk About Your Next Move

Thanks, Lee :)