If you're thinking about downsizing and you've spent the last 20 or 30 years living in York Region, one question keeps coming up: should I stay or should I go east? Durham Region is getting a lot of attention from downsizers right now, and for good reason. The price gap between these two neighbouring regions is significant, the 55+ communities are well-established, and the lifestyle options are broader than most people realize. But moving east isn't right for everyone. Here is an honest breakdown of where your home equity takes you in both regions, so you can decide which move fits your next chapter.
The Price Gap: Your Equity Goes Real Far East
This is the headline, and it's not subtle. In July 2026, the average home price in York Region was roughly $1.15 million. Over in Durham Region, the average sat at $856,000. That's a gap of about $294,000 — nearly three hundred thousand dollars separating comparable homes on either side of the regional boundary.
For a downsizer selling a family home in Newmarket, Aurora, or East Gwillimbury, that gap works in your favour. If your York Region home sells for, say, $1.2 million, and you buy a detached bungalow or a townhome in Durham for $850,000, you're walking away with roughly $350,000 in equity to invest for retirement. And that's before accounting for the lower property taxes and generally lower cost of living on the Durham side.
Within Durham Region itself, prices vary. Uxbridge is the most expensive at about $1.14 million average — it's the outlier because of its rural estate market. Whitby averages $868,651. Ajax sits at $868,651 as well (strong demand from Toronto spillover). Clarington (Bowmanville, Newcastle) is the most affordable at $787,979, where your equity stretches the absolute furthest.
The 55+ Community Scene: Two Different Approaches
Durham Region has quietly become Ontario's most active region for purpose-built 55+ adult lifestyle communities. And I mean purpose-built — these aren't just subdivisions where older adults happen to live. These are communities designed around what downsizers actually want: maintenance-free living, social programming, and single-level floor plans.
Wellings of Whitby (368 Taunton Rd E) is one of the most well-known. It's a pro-age community for independent adults 55+ with maintenance-free living, on-site amenities, and a full activities calendar. Lynde Creek Village in Whitby offers 113 homes with ten different floorplans, all designed for downsizers who want to stay active and social without worrying about snow removal or roof repairs. Port Perry Villa in Scugog gives you a small-town downtown, Lake Scugog waterfront, and an active adult community all within walking distance of each other.
York Region has 55+ communities too — places like the Heritage Place complex in Newmarket or the Delmanor retirement residences in Aurora. But these tend to be either higher-density condos or full-service retirement homes with meals and care included. The freehold bungalow-condo model — where you own your detached home but the association handles the grounds and exterior — is more prevalent in Durham. If the idea of owning a detached bungalow without the maintenance appeals to you, Durham has more options at better price points.
What You Leave Behind: The York Region Trade-Offs
Moving east is a great financial decision on paper, but I always tell my clients to be honest about what they'd be giving up. If you've spent decades in York Region, your people are here. Your doctor is here. Your favourite coffee shop, your grocery store, your walking route — those are all rooted in a place you know. Starting over in a new region, even one that's only 30 or 40 minutes away, can feel disorienting.
York Region also offers proximity to Toronto that Durham can't match — especially on GO Transit. The Barrie line from Newmarket or Aurora gets you to Union Station in about 55 minutes express. From Whitby or Ajax, the Lakeshore East line runs more frequently but takes about the same time. If you still commute downtown occasionally, the difference is minor. If you're retired and rarely go into the city, Durham's distance matters even less.
Healthcare is another honest consideration. Durham Region has Lakeridge Health hospitals in Oshawa, Whitby, Bowmanville, and Port Perry. York Region has Southlake Regional Health Centre in Newmarket and Mackenzie Health in Richmond Hill. Both regions are well-served, but if you have a specialist in York Region you don't want to lose, that alone might keep you where you are.
My Take "I've helped downsizers in both directions — some who stayed in York Region and some who made the move east. The ones who are happiest are the ones who matched the move to their lifestyle, not just their budget. The equity is real, but so is the feeling of home. I help my clients see both clearly."
Staying in York Region: Where Your Equity Can Still Work
You don't have to cross a regional boundary to downsize well. York Region has its own strong options for empty nesters, especially if you're willing to look at townhomes, bungalows, or condos rather than a detached house.
Newmarket is the best York Region bet for downsizers. Townhouse-style condos averaged $745,000 in mid-2026. You get a walkable downtown, the GO station, Southlake hospital, and all the services you need within a short drive or walk. The Davis Drive corridor and the area around Bristol Road have several newer townhome and bungalow-town developments that attract downsizers specifically.
Aurora has fewer entry points below $1 million, but pockets like the Aurora Highlands area offer bungalow condos and townhomes tucked into established neighbourhoods. The waitlist for some of these can be long, but they're worth exploring if you want to stay in Aurora's school catchment for grandkids or keep your existing community connections.
East Gwillimbury is the wild card for downsizers who want to stay rural but on a smaller scale. The newer developments in Queensville include some bungalow and ranch-style homes, and the Sharon area has older bungalows on larger lots that can be perfect for downsizers who want garden space without a four-bedroom family home.
The Property Tax Reality Check
Property taxes in Durham Region are generally lower than in York Region, though it depends on the specific municipality. Durham's 2026 budget included a 4.8% property tax increase, which is notable but still keeps the overall burden below most York Region towns. A detached home assessed at $850,000 in Whitby would pay roughly $6,500 to $7,000 annually in property taxes. The same home in Newmarket at $1.07 million would pay closer to $8,500 to $9,000. The savings add up, especially for retirees on fixed incomes.
So Which One Is Right for You?
After 19 years of helping downsizers navigate this exact decision, here is how I think about it:
- Choose Durham Region if maximizing your equity is your top priority, you want a purpose-built 55+ community with maintenance-free living, and you're open to building new routines in a new area. Whitby and Port Perry are especially strong options for downsizers who want walkable downtowns and lakeside lifestyle.
- Stay in York Region if your community connections, healthcare providers, and family proximity matter more than the maximum financial upside. Newmarket offers the best downsizer value in York, especially in the townhome and bungalow-condo market under $800,000.
- Consider Uxbridge if you want the best of both — Durham Region prices with a small-town vibe that's still close to York Region. Uxbridge averages higher than the rest of Durham at $1.14 million, but the trail system, the downtown, and the rural character make it a unique sweet spot for downsizers who want space without isolation.
The Bottom Line
Downsizing isn't just about cashing out equity — it's about finding the place where your next chapter feels right. I've sat at kitchen tables in Newmarket, Aurora, and East Gwillimbury and helped clients run the numbers both ways. Sometimes the obvious financial move turns out to be the wrong personal move. And sometimes the equity gap is so big that it opens a door you didn't know existed.
If you're thinking about downsizing and wondering whether to stay in York Region or head east to Durham, I'd love to talk it through. We'll look at the real numbers for your home, compare what your equity buys on both sides, and figure out which move actually fits the life you want next.
Don't worry, I've got this.
Thanks, Lee :)