Downsizing: Where Do You Even Start?

DOWNSIZING

Where Do You Even Start?

by John Merrill & Larry Osmond

September 12, 2026

For many homeowners, there comes a time when the family home simply becomes too much. Too many stairs. Too much maintenance. The kids have long since moved out and many rooms now go unused. Thoughts of a low-maintenance condo or even a retirement residence start to seem like a good idea.

Whatever the reason, deciding to downsize can be both exciting and overwhelming. And for someone who has lived in the same home for 30 or 40 years or more, it can feel like an enormous undertaking.

The good news? You don't have to figure it all out at once, or alone. The best place to start is by making a plan.

Start With the "Why"

Before worrying about boxes, furniture, or selling the house, take a step back and think about what you want your next chapter to look like.

Ask yourself:

• What has become difficult about my current home?
• What would make life easier?
• Do I want less maintenance?
• Would I prefer a condo, apartment or retirement residence?
• How much space do I realistically need?
• What location would be most convenient?
• What do I want to be closer to – family, friends, shopping, activities, and/or medical services?
• Do I want to be able to travel more and enjoy a more active retirement?

Having a clear idea of why you're moving and what you're moving toward can make the rest of the process much easier and helps focus your efforts on a goal.

Don't Try to Do Everything at Once

One of the biggest mistakes people make is looking around at a lifetime of possessions and thinking, "There’s so much – where do I even begin?"

The answer is: don't start with the whole house. Start with one room, one closet, or even one drawer.

Create three basic categories:

1. Keep: Things you use, need, or genuinely love.
2. Give Away: Items that could be useful to family, friends, or charitable organizations.
3. Dispose: Things that are broken, outdated, no longer useful, or have little value.

You don't need to make every decision in a weekend. Downsizing after decades in a home is a process, not a race. Give yourself time when sorting through possessions as you may have memories attached to them and, initially, you may be unsure which of the three categories some items belong.

Bring the Family Into the Conversation Early

Not all family members will be able or want to be involved in the various aspects of this process, but if family members are going to be involved, it's better to have the conversation early.

Some adult children may have opinions about what should be kept, sold, donated, or passed down. They may also have thoughts on where and when you should move. Sometimes those conversations are easy – sometimes they're not.

It can also help to ask family members what they would actually like to have before you start giving things away. But, remember to be realistic. Not every family member has room for the entire contents of a 2,000-square-foot house.

The goal isn't to find a home for everything. The goal is to decide what should come with you into the next stage of your life.

Talk to Your Realtor Before You Think You're Ready to Sell

This is one of the most important steps – and one that many homeowners overlook.

You don't have to wait until the house is decluttered, repaired, and ready for a photographer before talking to a Realtor.

In fact, talking to your Realtor early can help you create the plan that gets you there.

A good Realtor can help with much more than just the sale. They can identify:

• What repairs are worth doing before selling (and which ones not to bother with)
• What should be decluttered
• Furniture that could be removed or rearranged
• The estimated current value of your home
• What the current market looks like
• How long the preparation and selling process might take
• What the likely costs of selling will be
• How the timing of the sale can coordinate with your next move

Most importantly, your Realtor can help you develop a plan to work backwards from your desired move date.

For example, if you hope to move into a retirement residence in the spring, your Realtor can help establish when you should start sorting belongings and when the home should be prepared, assist with timely coordination of repairs, and identify the ideal time your home should not only go on the market, but how the closing date can fit into the overall plan.

With the preparation done and a plan in place, the actual sale can become much less stressful.

A Note on Renovations

After living in a home for decades, it's easy to look around and think, "We need to update
everything before we sell."

Usually, that's not necessary. Your Realtor can help you distinguish between things that need attention and things you shouldn’t worry about.
Often, efforts to prepare the house may include a fresh coat of paint, removing excess furniture, decluttering, improving lighting, a good cleaning, and addressing any important maintenance issues. Extensive renovations, though, are almost never part of the plan.

The objective isn't to create the perfect home. Instead, the goal is to make the house appealing to today's buyers while protecting your time and your money.

Additional Help – Ask Your Realtor

You don’t have to go it alone. Depending on your circumstances, you may benefit from various service providers such as:

• A cleaning company
• A moving company
• A painter
• A plumber
• An electrician
• A pest control company
• A junk removal service
• Charitable organizations that accept donations
• A professional organizer or senior move manager
• An estate sale company
• A financial planner
• A lawyer
• An accountant

Your Realtor will have a network of trusted professionals who regularly help homeowners through this process. The right team can turn an overwhelming project into a series of manageable steps.

The Bottom Line

If downsizing is on your horizon, don't look at the entire house and wonder how you're ever going to get it done. Talk to your Realtor and together you can build the roadmap to achieve your goals. It doesn’t have be daunting – the sale and next steps will be so much easier with the right plan in place. Once the plan is executed, you’ll be comfortably enjoying wherever your
next steps take you.

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