You’re not mad, are you?
About the four-part series, that is.
You were quite confident that the story would be told in a mere three parts, and you were looking forward to the conclusion on Monday.
Well, try as I might to fit both the purchase of the new house and the sale of the old one into a single post on Monday, I felt as though I’d be leaving out half the story if I put these two very distinct events together.
Not only that, TRB reader Andrew referenced a “trilogy,” and it made me aspire to something greater…
The truth is: anybody who has bought and sold real estate will tell you that it is, in fact, two different adventures. Sometimes it’s easier to buy, sometimes it’s easier to sell. Some folks think the buy-side is more daunting, takes longer, or is more anxiety-inducing, and others have those feelings associated with the sale.
Buying the new house for my mother may have taken six years, from idea to implementation, but I think it represented the easy part.
Selling my mother’s house was not going to be an easy task.
Not only was the house located in Scarborough, which was not a healthy market, but it also needed work. This would come in two forms:
1) Emptying the house.
2) Repairs and renovations.
My mother will kill me if I make it sound like she was a pack rat, so trust me when I say that she runs a tight ship over there. In fact, a lot of the “stuff and things” that would need to be taken out of the house belonged to my brother, sister, and me!
Raise your hand if you’re forty-five years old and you still have possessions in storage at your parents’ house?
Well, time moves quickly, and while we might have started to fill mom’s house back in 2003 or 2004, here we were in 2026 looking back at the fact that much of our crap had been sitting there for over two decades.
I started by explaining to my mother that there were three important facets of the process:
1) Pricing
2) Preparation
3) Listing
For pricing, I knew enough through my experience in the business to know that I couldn’t do this myself.
Why?
Because I was emotionally involved.
Any time I see a real estate agent selling his or her own house, I shake my head. This is an emotional a process as any, and there’s no way for an agent to avoid getting in their own way.
I asked Chris, Matthew, and Tara to do an independent Comparable Market Analysis for my mom’s house, and we set a day to meet.
Of course, they all applied a lower price to the home than I did.
I sat in the conference room at Bosley Real Estate, arguing with the three of them, pleading my case. But in the end, I realized this was exactly why I had asked them to price the home in the first place.
While I was hoping the house was worth $1,300,000, the consensus was that it was worth $1,200,000.
“On a good day,” Chris told me. “Remember, this house is in Scarborough. We sell houses in Bloor West Village, Leslieville, Leaside, the Beaches, and other family areas in the central core. I know you love your Mom’s house, but don’t lose sight of the fact that this isn’t a seller’s market.”
We decided to price the home at $1,099,000, with an offer date, even though that strategy didn’t work in my mom’s neighbourhood, but this was because of the preparation and presentation that we had in mind.
Case in point, this is a photo from a comparable house on her street that sold last year:

Old and empty.
That is not how we sell real estate.
We were going to take our dog-and-pony show on the road to Scarborough, and sell a house there how we would sell it over here.
For preparation, I explained to my mother that it was going to take a Herculean task to get the house ready. Not only would we have to pack 90% of the house into storage bins, put them in a moving truck, and take them to storage, but we’d also have to do repairs and renovations in the house.
Our upgrade list contained the following:
-Refinish hardwood flooring
-Paint kitchen cabinets
-New hardware on kitchen cabinets
-New kitchen counters
-Upgrade existing light fixtures
-Paint the majority of the house
-Pressure-wash back deck
-Miscellaneous repairs inside/outside
My mother was completely on board.
Our budget for the work was about $15,000, and we put a timeline in place.
But first, we would have to get the house empty, and that was a whole other world of work.
So how do you start? Where do you start?
When I explain this to clients, I always provide them with the same childish riddle:
How do you eat an elephant? One bite at a time…
I told my mother, “Maya and I are coming for dinner on Sunday, but we’re going to come early. It’s going to be a blue-collar engagement!”
I figured that we would start with the most annoying task of all, but one that would make a huge impact: pack away all the tchotchkes.
One person’s tchotchke is another person’s priceless family heirloom, but you know what I mean.
My mother has a massive collection of shot glasses, but every vase, china plate, and piece of glassware needed to be bubble-wrapped and tucked into a large plastic tote.
Here’s a photo from that first evening of packing:

We filled three 102-litre plastic totes with just the delicate items, and then moved on to see what else we could accomplish that afternoon.
We began collecting items from all around the house and simply bringing them to the living room and dining room, which represented a “hub” of sorts. It was from there that we would decide whether to pack them in bins today or leave them for a later push.
While this might sound like simple work to many of you, don’t underestimate how emotional it can be if you haven’t done it.
What’s it like to take these off the wall, after twenty-four years, and put them into a storage bin?

We also packed the “Fleming Family Photo Archives,” which many of you can relate to. Picture an entire wall filled with albums from the 1970’s through the 2000’s.
These albums alone took about six full plastic totes, and they were heavy as hell.
Then, we’d have to remove the shelves that housed the albums for the last two decades, which were bolted right into the wall studs. Add this, and the repairs and painting, to the reno/repair list for later.
By the time the three of us had quit that first evening, we had made a pretty big dent:

But that was only the beginning!
During the week, my daughter actually seemed excited to head back on Sunday and continue packing. She was just so curious about all the treasure she was uncovering in every nook and cranny throughout the house.
The following weekend, it was time to get to the existing storage bins that hadn’t been touched since the early 2000’s.
And by that, I mean the stuff that belonged to my brother, sister, and me.
You wouldn’t believe how much stuff there was. Or maybe you would? Have you been through this process?
The irony is: this storage solution was originally supposed to be “temporary,” but twenty-four years go by quickly.
We unearthed some epic treasure.
I mean, do you still have your soccer trophies from 1996? Because apparently I do…

I completely forgot: I had labelled every single one of them with the year, team, division, and stats.
God, I was such a nerd. Was, as in, past tense, right?
We packed every piece of artwork, every toy from the kids’ playroom, and just about everything that would not be part of staging and presentation for the home once it was listed for sale.
But the best thing we found in the entire house?
Hands down, no question, it was this:

A quick poll of the older folks out there: do you still have your wedding dress? And if so, from what year?
It took us two weeks, but we eventually packed up most of the house and put it into storage. This consisted of about thirty-five 102-litre plastic totes and a dozen picture frame boxes.
Then, it was time to renovate!
There were two major renovations planned that would make it impossible for my mom to stay in the house:
1) Refinishing the hardwood floors.
2) Painting the kitchen cabinets.
Now, there are multiple ways to paint kitchen cabinets. Some people will simply paint the cabinets with a brush as the cabinets remain on the hinges! We’ve been known to do that, from time to time, for lower-end properties where the stakes aren’t as high, and the buyers aren’t as discerning. But for this kitchen, we had to do it right…
My mother moved into our house for eight days while we got to work.
Here’s a look at the kitchen cabinet process:

The cabinets were originally that light brown colour that was so synonymous with the early-2000’s, but we painted them white.
White is modern. White goes with anything.
And as you can see, we took the doors off and had them sprayed.
Painting kitchen cabinets has a huge impact, but leaving the original laminate countertops is always a mistake.
So, we did that too:

There are a lot of other things we could have done, such as a new backsplash or floor tile, but pre-listing renovations are about making the largest impact for the lowest cost.
We had the floors refinished, too, which took several days and was a fantastic mess.
We painted most of the house, including the bathroom vanities, and then swapped out five or six light fixtures.
After all was said and done, we were ready to go to market!
My mother went to London, England to stay with my brother’s family while we were listed for sale, and upon her return, she came back to stay with us again.
It was like she never left!
We listed the property for $1,099,000, with an offer date, even though this was a strategy that wasn’t that successful in the area.
Again, my team continued to caution me in order to temper expectations.
I suppose here’s where I need to make a very important disclosure:
I have never listed my own property for sale.
Real estate agents have a habit of getting in their own way, and I will be the first to admit this.
Every time I have sold my primary residence, I’ve had a colleague list it in their name and run point on the listing, answer questions from agents, and run the offer nights.
Humility is scarce in our industry, and it takes a lot for an agent to realize their emotional involvement and potential bias before stepping aside.
Since this was my mother’s house, and not mine, I still listed it in my name. But my team took a large role in the process.
We listed on a Tuesday with offers scheduled for the following Monday evening, which is how I typically like to run a listing.
Showings were consistent through the week, and our open house on the weekend was quite busy.
I came into the process hoping the house was worth $1,300,000, but my team felt it was worth $1,200,000. That’s ironic, isn’t it? Almost like I was getting a dose of my own medicine!
We had about thirty showings through the week, and another fifteen groups came through over the open houses on Saturday & Sunday, and when Monday rolled around, I was a little nervous.
There was one agent who had been bugging me all week, and I felt he was my “lead horse,” if you will.
We had five registered offers, and as is usually the case, two were very, very poor.
But my “lead horse” wasn’t in the lead. It was quite surprising, since he and I had discussed pricing and comparable sales during the week, but he was in second place, and didn’t seem motivated to improve.
I spun my wheels with these five offers from our 6:00pm presentation time well past 9:00pm, but I was stuck.
The highest offer was $1,180,000.
It was obviously well below what I had originally hoped the house would fetch, but it was even below what my team said it was worth!
I started to consider my options.
Would I simply reject the offers in hand and see what happened the next day? Maybe one of those buyers would have some regret and increase their price?
Perhaps I could just re-list the house later that week for $1,249,000 and see how it went?
It was around this time that Chris stepped up to the microphone and asked me a very, very important question:
“Dude, are you fucking crazy?”
Like I said: an important question.
I would have assumed the answer was an emphatic “no,” but Chris had other opinions on the matter.
He explained:
“Your Mom’s house is in Scarborough. Open your eyes, man. You’ve got five offers on a house that’s in an area where houses take six months to sell. The goddam house four doors down has been listed since January. The market has spoken. You have a firm offer where nothing sells without a condition. You did your job. Take the $1,180,000 and move on.”
This is why agents shouldn’t list their own houses for sale. Because they don’t talk to themselves like this.
Selling your home is an extremely emotional process, and even the world’s most brilliant sociopaths can’t keep their biases and feelings out of it.
I thought that because this was my mother’s house, I would be prudent, but now people were telling me that I was being anything but.
I told Chris, “I feel like I failed. I couldn’t even get to $1,200,000. I was nowhere near my goal.”
Chris said:
“David, you bought your mother a house and she’s moving two minutes away from you. That is your win. Six weeks from now, is that sale price gonna matter?”
I know he means business when he calls me “David” instead of “Dave,” so this was some pretty serious talk.
I heard from Tara as well at one point, who was just checking in and offering some words of encouragement.
I mulled it over a little bit more, but before I could make any decisions, I received yet another phone call.
It was Christan Bosley, the Broker of Record of Bosley Real Estate.
She asked me how it was going, in her classic, cool demeanour, and I explained what had transpired thus far and what I was thinking.
I honestly wondered if Chris had put her up to the phone call, but to this day, I still don’t know.
She reminded me, much like Chris had done previously, that we were not in Roncesvalles, nor were we in Bedford Park. We were in Scarborough, we had five offers, and any other seller in the area would kill to be where we were.
She asked me to envision the scenario where we do not sell the house and where we keep it listed through May, into June, and then into the summer. Maybe it sells in August, but maybe it sells in September. And maybe the buyer wants a long closing date, which we might have to provide, if we have absolutely no leverage. When all was said and done, maybe we could close the sale at Christmas?
That was it.
My team had convinced me. I believe I would have ultimately come to the same conclusion, but I needed them to reinforce it for me as well as expedite the process.
This turn of events might surprise some of you, but trust me when I say that there is a lot of collaboration behind the scenes with real estate agents, and I have a great team to support me.
I went home around 10:30pm, and my whole family was asleep, except for my mother.
She was sitting on the couch, knitting, and watching CNN at a volume that would wake up the dead.
I told her, “Mom, we’ve got $1,180,000, and we’re closing on July 1st.”
She said, “David, that is incredible! $1,180,000, really?”
It’s so cute because three days earlier, when I told her that maybe we could get a bully offer, she said, “Nothing short of $1,300,000, though.”
She can be so impulsive and so quick to change her tune, but when she does so, it’s always out of pride or happiness.
I could have told her we were selling for $800,000, and she’d have said, “That’s amazing! Great job!” So there’s a window into my childhood, but that’s a topic for another day…
I was wired that night and probably didn’t fall asleep until 2:00am, but I had a lot to process.
The next morning, my son was sitting at the kitchen counter eating breakfast, and he said, “Daddy, did you sell Ammy’s house last night?”
He’s 6-years-old and neurodivergent, so it often surprises me that he shows us that he takes in everything that goes on around him, even if he doesn’t show it.
I said, “Yeah, buddy, I did.”
He took a bite of his waffle and said, “Good, because I don’t like going to her old house, it’s too far, and I don’t like being in the car for so long.”
Good to know that he wasn’t focused on the price, eh?
All’s well that ends well, and this ended well. Very well, I would come to feel over the following weeks.
We took possession of my mother’s new house in May, and while it took some time to get the necessary permits for the renovation, we’ve completed the monumental asbestos removal and done the demolition, so we’ll be starting the fun part shortly!
Speaking of which, here’s the “craft area” in the basement that my mom is the most excited about:

Those are opposing walls, by the way. I think you get the gist of it.
With any luck, my mother will be moved into her new house by mid-July, but if the timing doesn’t work, we’re more than happy to have her stay with us for as long as she needs to.
So there you have it, folks.
Just a very basic six-year process to downsize, summarized in a brief 14,000-word novel that spanned two weeks. 🙂
If you’re looking to downsize or are working with a family member who is, just remember that there’s no right or wrong way to do it. Just go at your own speed, and if you ever have doubts, stop and remind yourself why you’re doing it. Picture your endgame.
Thanks for reading, folks!
Have a wonderful weekend.
David.

