Buying a Home in the Middle of Winter Was the Worst Thing I Ever Did—And I’d Do It Again

Where I live in Boston, housing isn’t just challenging—it’s borderline impossible. There’s just not a lot of space to build new units, and much of what’s available are high-end, luxury apartments. I’d call it a bubble, but it’s more a shortage of affordable options. Nevertheless, my husband and I managed to sneak into a competitive Boston neighborhood, buying a two-bedroom condo with a lower mortgage than the rent in our glorified studio. We worked with a seller who was offloading to build something new and obtained a “deal” (still paying a cool half a million dollars, mind you) by searching in the winter. We’re now hopefully in a good place to afford other Boston real estate, should we ever move, and we love our proximity to the rest of the city. Normally I might not encourage anyone to do what we did, because of the challenges involved, but sometimes it’s the only way. Here’s what to know when buying a house in the dead of winter.

Pro: No one else is looking in winter

When my husband and I started looking at houses in spring 2016, open houses were an unholy nightmare. We’d line up with dozens of other miserable-looking couples, while older buyers bragged loudly about how they had the cash to buy outright and leered at us nastily. Brokers used phrases like “basically turnkey” and “move-in ready” while we filed past walls with gaping holes and exposed wiring. It’s no coincidence that I started to have anxiety attacks afterwards. By November, though, the herd had thinned, and it felt like I could at least see a space without 40 other pairs of eyes on me. Understanding what your budget will buy, and how the market fluctuates, is a crucial part of the process. It didn’t feel like our search had started in earnest until then.

Con: There’s less available

Part of the reason spring and fall are so popular for sellers is because that’s when people are looking. At least in Boston, fall is competitive because Sep. 1 is when most leases start, and spring is for parents who want to relocate their families before the next school year. So, it makes sense for sellers to follow supply and demand, especially when there’s not a lot of new housing. With fewer crowds comes less inventory. We felt uninspired, but we strapped on our winter boots and went to look anyway.

Pro: There are “pockets of availability” 

That term comes directly from a local housing seminar we attended. The Boston housing market is already overpriced, and during peak season units can go for thousands of dollars over asking price. So, avoid those times. You’ll usually find highly motivated sellers off-season and “deals”—houses that might be sold at asking price, without a dozen competitive offers. The only thing is that a few other savvy buyers might have the same idea as you. We almost lost out to another bid because they caught wind of the deal we might be getting. So, act fast when you spot something you love.

Con: Moving in the middle of winter sucks

On the day of our move in March 2017, it snowed. And not that light, fluffy stuff that melts immediately. Our moving truck managed to get lost, so by the time it arrived, at least an inch of slippery, icy snow had accumulated on the sidewalk, our stairs, and the driveway. And then, ultimately, inside the house, too, as the damp movers moved our damp boxes into the middle of our now-frigid condo. The whole process was extremely unpleasant, but we were sustained throughout with the comforting thought: This is what saving money on Boston housing looks like. Over two years later, I don’t regret a thing—even if I dread the next time, we must trudge to open houses in the dead of winter to find our next place.



Credit: Diana Paulson

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