I get this question a lot, usually over coffee, sometimes over the phone from someone who's just started thinking about it and isn't ready to tell anyone else yet. "Is now a good time to downsize?" And the honest answer is — it depends less on the market than most people think, and more on your own situation than you might expect.

I've been doing this work on the North Shore for 25 years now, and I hold the SRES® designation specifically because I work with a lot of people navigating this exact decision. So let me walk you through how I actually think about it, rather than giving you a generic answer.

What "Downsizing" Really Means

Downsizing isn't always about square footage. Sometimes it's about stairs. Sometimes it's about yard work you no longer want to do, or a house that was perfect for raising a family and now just feels too big and too quiet. Sometimes it's about being closer to your kids, or further from harsh winters, or simply wanting less to manage.

Whatever your reason, the "right time" question usually comes down to three things: your home's condition and value, your next-step housing options, and your own readiness. Market conditions matter, but they're rarely the deciding factor.

What the Market Looks Like Right Now

Looking at the most recent Essex County single-family data, a few things stand out. Homes that sold this year took a bit longer to find a buyer than last year — an average of 36 days on market, up from 32 — and sold for about 102% of list price, a small step down from last year's 102.9%. That's still a strong number for sellers, just not quite as competitive as it was twelve months ago.

At the same time, listing inventory is up nearly 19% compared to this time last year, and the approximate months of supply has grown from about 1.6 months to 2.0 months. That's still tight by historical standards — it's not a buyer's market — but it does mean sellers have a bit less urgency working in their favor than they did a year ago, and buyers have somewhat more to choose from.

For downsizers, that combination is actually worth paying attention to on both sides of the transaction. If you're selling a larger home, you're likely still in a favorable position, though perhaps with a slightly longer runway than last year's sellers had. And if you're buying a smaller single-family home or condo next, that modest rise in inventory may give you a little more room to be selective than buyers had a year ago.

This is actually one of the more overlooked parts of downsizing. Sellers sometimes focus entirely on what they'll get for their current home and forget to think through what it will take — and how long it might take — to find and secure the next place. I always encourage clients to think about both sides of that transaction together, not separately.

Financial Considerations Worth Thinking Through

Every situation is different, and I'm not a tax or financial advisor — for anything involving capital gains, estate planning, or tax strategy, please talk with a qualified CPA or attorney before making decisions. What I can help with is the real estate side: what your current home is realistically worth in today's market, what comparable smaller homes or condos are selling for in the towns you're considering, and how to structure the timing so you're not carrying two mortgages or scrambling for temporary housing.

A lot of downsizing plans get built around finding your next place first, then selling. Others work better selling first and using a rent-back or extended closing to buy some breathing room. Neither approach is universally right — it depends on your comfort level and your specific finances.

The Part Nobody Talks About: Emotional Readiness

I'll say this plainly because I think it deserves to be said plainly: downsizing is often more emotional than financial. If you've raised a family in your home, or lived there for decades, deciding to leave can bring up a lot more than spreadsheets and square footage. That's normal, and it's not something to rush through.

Part of my job — and something I take seriously — is giving people the space and information they need to make this decision on their own timeline, without pressure. Some of my clients decide to move within a few months. Others spend a year or two thinking it through before they're ready. Both are fine.

Practical Signs It Might Be the Right Time

Rather than a checklist, here's how I'd frame it in conversation, because that's genuinely how I think about it with clients: If your home needs more upkeep than you want to manage, if the space no longer fits how you actually live day to day, if you're spending money maintaining rooms you rarely use, or if you find yourself thinking about a smaller, simpler home more often than not — those are all reasonable signals worth exploring further. None of them mean you have to act today. They just mean it's worth having a real conversation about your options.

How I Help North Shore Homeowners Through This

Because I hold the SRES® designation, working with clients through senior transitions and downsizing is a meaningful part of my practice — not an afterthought. That usually starts with an honest conversation about your home's current value, a look at realistic timelines for both selling and buying, and a plan that fits your pace, not a sales quota. I also work closely with clients handling estate and probate situations, which often overlaps with downsizing decisions after a parent's passing.

If you're in Salem, Beverly, Danvers, or one of our other North Shore communities and you're starting to think about this, I'd genuinely rather have an early, no-pressure conversation with you than have you make a decision without good information.

Jim Armstrong

REALTOR® | SRES®, ABR®, GREEN | Armstrong Field Group at Aluxety Real Estate

Jim has served North Shore homeowners for over 25 years, continuing a family legacy in Salem real estate that began in 1944. He specializes in senior transitions, estate sales, and helping longtime homeowners navigate downsizing with clarity and no pressure.