Downsizing Without Rushing: A Windsor-Essex Guide to Your Next Move

Downsizing isn’t one decision, it’s a season of planning. This guide breaks down your best next steps, including right-sizing without moving, cost factors in Ontario, and how to build a low-pressure shortlist.

Downsizing gets framed like a single decision: sell the house, buy something smaller, move on.

In real life, it’s usually a long season of thinking, planning, and quietly weighing what matters most: comfort, cost, maintenance, location, lifestyle, and what you want the next chapter to feel like.

If you’re considering downsizing in Windsor-Essex but you’re not ready to pull the trigger, you’re in the sweet spot to make smart moves now that create options later. Here’s how to do it without rushing, and without making a move you regret.

Why so many people “think about it” for years

Aging in place is common, and it’s not just a preference, it’s often the most practical choice. Canada’s population is aging quickly, including a fast-growing 85+ group, which is one reason housing needs and accessibility are becoming bigger conversations. (You’re not imagining that this topic is everywhere.)

CMHC has also noted that the likelihood of seniors selling tends to peak in more advanced age groups, which fits what we see locally: people often wait until the move is clearly worth it, or necessary.

So if you’re not ready yet, that’s normal. The goal is to use this “in-between” time strategically.

Step 1: Get clear on what you’re actually downsizing for

Downsizing is not about square footage. It’s about friction.

Common “friction points” I hear from Windsor-Essex homeowners:

Yard work and snow removal are starting to feel like a second job
Stairs are fine today, but you’re thinking ahead
The house is great, but it’s not close to what you do most
You want to free up cash flow or reduce monthly costs
You want less “stuff management” and more living

Quick exercise: Rate each of these from 1 to 10 for your current home:

Maintenance workload
Monthly carrying cost comfort
Layout for the next 5 to 10 years
Location convenience
Emotional attachment (this one matters)

Your lowest scores are your clues. That’s what your next move should solve.

Step 2: Decide which “downsizing path” fits you

Most people assume there are only two paths: stay or sell.

There are actually at least four, and choosing the right one makes everything feel easier.

Option A: Downsize later, but prepare now

This is the most popular and usually the smartest.

What to do now:

Start decluttering by category (not by room). Clothing, books, kitchen, decor
Digitize paperwork (especially manuals, warranties, tax records)
Do a “pre-inspection mindset” walkthrough and tackle little issues before they stack up

This reduces stress later and often improves your future saleability.

Option B: Right-size without moving (the contrarian option)

If the home still works, keep it and remove the pain.

Two big levers:

Reduce maintenance: hire out lawn care, snow, and seasonal tasks
Improve accessibility: add practical upgrades like railings, lighting, non-slip flooring, stair support, or a main-floor laundry setup

Canada has a federal tax credit for home accessibility expenses (line 31285), with eligible expenses up to $20,000 per year for a qualifying individual (65+ or eligible for the Disability Tax Credit).

This is a very real way to “stay put” safely while keeping your future options open.

Option C: Buy the next home first, then sell later

This can work well if:

You want time to renovate the new place
You want to move slowly and avoid pressure
You’re picky about layout and location

It’s more complex financially, but for the right person, it’s calm and controlled.

Option D: Partial downsizing (rent out space or add income)

Not for everyone, but worth mentioning:

Separate entrance suite
Rent a room to a student or traveling professional
Short-term rental where permitted and practical

Sometimes “downsizing” is actually “making the home pay you back.”

Step 3: Know what downsizing really costs in Ontario

People focus on the sale price difference, but the math is wider than that.

Typical cost buckets:

Legal fees and moving costs
Mortgage discharge or refinancing costs (if applicable)
Land transfer tax on the purchase (Ontario rules apply, and special taxes can apply in specific cases)
Condo fees (if you go condo)
Renovations or accessibility updates in the next home

The point: downsizing is not always an immediate financial win. Sometimes it’s a lifestyle win first, and a financial win later.

Step 4: Build a “downsizing shortlist” based on lifestyle, not trends

In Windsor-Essex, downsizers often compare:

Ranch and ranch with bonus layouts
Townhomes (freehold vs condo)
Condos (amenities, fees, parking, elevator reliability)
Smaller lots in walkable pockets (LaSalle, Amherstburg, Riverside, Tecumseh, Kingsville, Lakeshore, and more)

Your shortlist should be built around:

Main-floor living
Low exterior maintenance
Storage that feels right, not cramped
A location that supports your weekly routine (groceries, medical, family, social life)

If you want, our team can build a “right-size watchlist” that updates you quietly without pressuring you to move.

Step 5: Use a “soft timeline” so you don’t feel trapped

If you’re not ready, don’t force a deadline. Use a trigger.

Examples of good triggers:

“If a bungalow in X area becomes available under X price, I’ll view it.”
“If maintenance starts to feel like a burden twice a month, we re-evaluate.”
“If stairs become annoying, we explore one-floor options.”

This creates momentum without stress.

A simple plan you can start this month

Week 1: Declutter one category (clothes, books, kitchen, decor)
Week 2: Make a repairs list (tiny stuff first)
Week 3: Review your monthly costs and what you want to reduce
Week 4: Identify 2 to 3 neighbourhoods or building styles you’d actually move into

That’s it. You’re not “behind.” You’re preparing like a pro.

How The Dan Gemus Real Estate Team helps (without pushing you)

If you’re in the thinking stage, we can support you with clarity, not pressure:

A realistic home value range and what would improve it
A personalized downsizing shortlist (bungalows, townhomes, condos, low-maintenance options)
A planning conversation that compares “stay and modify” vs “move and simplify”
Timing strategy if you want to move later, but you want to start preparing now

If you want to talk it through, reach out anytime at www.dangemus.com.

This blog is not intended to replace legal, accounting, financial or tax advice, nor is it intended to solicit those currently under contract with another Brokerage.