How these millennials climbed the property ladder during the pandemic

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Who they are: Jeff Cartwright, 35, vice-president at S.I. Systems, a recruiting company; Brianna Cartwright, 31, ultrasound technologist at Sunnybrook Hospital; their five-month-old son, Camden; and their seven-year-old Yorkipoo, Paisley.
The climb: In 2016, they bought a 1,600-square-foot two-bedroom, one-bathroom detached in East York for $930,000. Then, in May 2020, they sold that place for $1.3 million. Four days later, they bought a 3,000-square-foot four-bed, four-bath detached in East York for $1,385,000.

Brianna: Jeff and I are both from Ontario—I’m from a town called Walkerton in Bruce County, he grew up in Markham—but we both moved to Calgary after college, basically to try something different. I’d just graduated from McMaster and was working as an ultrasound technologist. Jeff studied audio engineering but ended up working in HR. We met in 2013, got our dog Paisley and have been pretty much inseparable since.

Jeff: We got married in 2016 in the backyard of my parents’ place in Walkerton with 130 guests. It was beautiful. At that stage, we’d both been living out west for a good chunk of time and wanted to come back to Ontario to start a family. So, we plotted our move. Luckily, I was given the opportunity to take over eastern Canada for my recruiting company. They even gave me a moving allowance. And Bri found a job at Sunnybrook Hospital.

Brianna: In October 2016, we bought a two-bed, one-bath detached in East York for $930,000. It was built in the early 1900s and had two big bedrooms and a lovely backyard. We did some cosmetic renovations: sanding the floors, repainting the walls, redoing the kitchen. It cost about $15,000. Then we started trying to get pregnant, but it didn’t happen as easily as we’d hoped. We did a few different fertility treatments and ended up trying IVF in 2019. Shortly after, we got the phone call. We were pregnant.

 Jeff: Our son, Camden, was born in February. Then Ontario went into lockdown and my company decided that everyone should work from home.

Brianna: During quarantine, we started to realize the house had some drawbacks. If we wanted to have more kids in the future, we would definitely need more square footage. Plus, the thought of four or five people sharing two bedrooms and a bathroom wasn’t ideal.

Jeff: In April, my sister showed me House Sigma, a real estate app that makes it easy to watch trends. We’d heard all the reports about house sales hitting record lows, but when I looked at the app, I noticed a shortage of supply in East York. People weren’t listing their houses because they were worried about the state of the market, so there wasn’t much available. But I could see that everything on the market got snapped up right away. There was demand there, and with Camden so young, we thought it might be good to sell before he grew accustomed to the area.

Brianna: To decide on the listing price, we looked at other sales in the area and got a drive-by evaluation from the bank, which valued the house at $1.25 million. We thought with our renovations and some nice staging, we could stretch that number to $1.3 million. That became our magic number and we wouldn’t sell for anything less. Jeff’s high school friend Jesse is a realtor, and when Jeff showed him the data on recent sales, he decided to help. In fact, he was so convinced that he could get us our magic number that he shelled out $5,000 for staging and marketing.

Brianna: On May 20, we listed for $999,000. The level of interest was crazy. We had 58 people come for in-person viewings. I think it was a combination of pent-up demand, the low price and Jesse’s marketing. Over the course of a week, Jesse arranged for potential buyers to get the keys and view the house one after another. We made everyone sign a waiver, too, indicating they hadn’t come in contact with the virus. And we moved to Jeff’s parents’ place in Stouffville for the week, both for safety reasons and because we wanted to avoid the hassle of having to clean up baby toys every time someone came through.

Jeff: Offers were due the following week. We had seven bids, ranging from $1.1 million up to $1.25 million. After speaking to Jesse, we wrote back to the top five buyers and asked them to resubmit. The top offer went up by $50,000, raising the total to our magic number, $1.3. We settled on a 60-day closing date in late July.

Brianna: After selling, our plan had been to sit tight and not buy a new place for a few months. Since we weren’t commuting to work, we could stay at Jeff’s parents’ place and start looking for a house in the fall, when maybe the market really had dropped off a little. Then Jeff spotted another place on House Sigma.

Jeff: Bri had actually seen this four-bedroom, four-bathroom house online a few weeks earlier. It was only a 10-minute walk from our old place, and it had a big backyard overlooking Taylor Creek Ravine. For some reason, it still hadn’t sold. It was listed for $1,489,000, which was more than we were willing to pay, but we decided to check it out anyway. We got our gloves and hand sanitizer and went to check it out. That was on May 30, only four days after we’d sold our place.

Brianna: As soon as we walked in the front door, we looked at each other as if to say, “This is massive.” The place was 3,000 square feet, about twice the size of our old place. I immediately thought about knocking down the walls on the main floor to make it open concept. It had a massive backyard, four bedrooms, a one-car garage and driveway parking for four. It really seemed like the type of place that we could grow into.

Jeff: When we were looking at the basement, there was a computer with an Excel spreadsheet open. On the spreadsheet, they had June 1 marked as “moving day.” We assumed that meant the owners wanted to be out of the house by then, which suggested we were dealing with a motivated seller. So we made a low offer of $1,375,000 with a 60-day close, because we figured a quick closing date would be key for them.

Brianna: They rejected the offer and asked us to come back with something better. Jeff wanted to go up to $1.4 million, but Jesse had the feeling that we were very close. He convinced us to up our offer by $10,000 and offer a 30-day closing. That’s what we did. Jesse called us back 10 minutes later and gave us the good news. “Guys, you’ve just bought a new house.”

Jeff: Because of the short closing time, we had to get bridge financing to help us buy the new place before closing on the last one. We plan to recoup some of that money by moving everything ourselves and not paying a moving company. After we officially close on July 29, we plan to live with my parents and completely renovate the main floor, which should cost about $300,000.

Brianna: I look back and think that we’ve been really fortunate over the last five years, especially considering everything that’s happening now. It’s so difficult to break into the market in Toronto. Jeff has his finger on the pulse, so we’ve made some good decisions and capitalized on our opportunities.

Jeff: We’re still hoping to move in the fall, or at least by Christmas. Between having Camden, dealing with the virus, selling a house and buying a new one, it’s been a big 2020 for us. But we definitely want to have more kids, so things might be this crazy for a while.