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After decades in your family home—where you’ve celebrated holidays, raised children, and created countless memories—the thought of downsizing can feel both liberating and terrifying. The rooms that once bustled with activity may now feel empty, and those stairs might be getting harder to navigate.

Before you put that “For Sale” sign on your lawn, take a moment to reflect on these five essential questions. Your answers will help ensure your next chapter is the right one for you.

1. What Do You Really Want Your Next Chapter to Look Like?

This question goes beyond square footage or the number of bedrooms. It’s about lifestyle.

Ask yourself:

Do you want to be within walking distance of amenities like coffee shops, libraries, or parks?
How important is having easy access to transit and healthcare facilities?
Do you want to eliminate yard work and exterior maintenance entirely?
Are you seeking a community of like-minded peers or a diverse neighbourhood?
How much time do you plan to spend at home versus travelling?
How important is maintaining connections with your current community and neighbours versus starting fresh?
What hobbies or interests have you put off pursuing that your next home could accommodate?
What balance of privacy and social interaction would make you happiest day-to-day?
How would your ideal living situation support your personal definition of “ageing well”?

Many downsizers discover what they’re really seeking isn’t just a smaller home, but a different way of living. Some find joy in vibrant urban settings after years in the suburbs, while others prefer the quieter pace of smaller communities outside Toronto, where their housing dollars stretch further.

Remember: This move isn’t just about what you’re leaving behind, but what you’re moving toward.

2. Have You Honestly Assessed Your Long-Term Health and Mobility Needs?

The two-story home that serves you well today might become challenging in five or ten years. Considering potential mobility issues isn’t pessimistic—it’s practical.

Consider:

Would single-level living suit you better as you age?
Are features like step-in showers, wider doorways, and accessible kitchens important?
Is the property manageable if you develop mobility issues?
Would features like elevators (in condos) or minimal steps become important?

Many downsizers find themselves moving twice in retirement—once when they initially downsize, and again when health issues necessitate it. Planning ahead might help you avoid that second move.

3. How Will This Decision Impact Your Financial Future?

Downsizing often frees up equity, but the financial picture isn’t always straightforward.

Think about:

After selling costs and purchasing a new home, how much equity will you actually access?
How will monthly carrying costs compare (property taxes, maintenance, utilities, condo fees)?
Have you factored in moving expenses and potential renovations to your new space?
Will your new location impact your cost of living (transportation, services, amenities)?
How does this move fit into your overall retirement financial plan?

Many downsizers are surprised to discover that while they reduce their mortgage or eliminate it entirely, other costs can offset some of those savings. Your financial advisor can help you run the numbers specific to your situation.

4. What Are Your Options Beyond Traditional Downsizing?

The choice isn’t simply between staying put or buying a smaller property. Creative alternatives exist that might better suit your needs.

Explore:

Could renovating your current home to include a rental unit provide income while allowing you to stay?
Is a multi-generational arrangement with adult children possible and desirable?
Would a “snowbird” lifestyle with a smaller Canadian home plus a vacation property work?
Have you considered co-housing arrangements with friends or family?
What about continuing care retirement communities that adapt as your needs change?

For some, the answer isn’t downsizing but “right-sizing” in creative ways.

Related: Rent vs. Buy Over 65

5. What’s Your Emotional Readiness for This Change?

This may be the most important question, yet it’s often the least discussed. Leaving a long-term family home involves grief, even when the move is practical and desired.

Reflect on:

How do you feel when you imagine leaving your current home?
Have you given yourself permission to acknowledge the emotional aspects of this transition?
Are you making this move because you want to, or because others are pressuring you?
Have you visited and spent time in the type of community you’re considering?
What would help make this transition feel more positive than painful?

Many downsizers benefit from visiting potential new communities multiple times, staying overnight when possible, and imagining daily life there before making decisions. Others find that keeping a few meaningful items from their family home helps bridge the emotional gap.

Moving Forward: The Decision Is Yours

There’s no universal “right time” to downsize. Some people thrive by making the move while they’re young and healthy enough to establish new routines and connections. Others find innovative ways to adapt their existing homes to changing needs.

What matters is that your decision aligns with your values, lifestyle preferences, and long-term well-being. Take your time, explore your options thoroughly, and remember that this next chapter holds the potential for new freedoms and experiences.

After all, downsizing your space doesn’t mean downsizing your life—in fact, many find just the opposite to be true.

The 5 Questions to Ask Before Downsizing