The Great Real Estate Adventure

Patience, rejection, sacrifice, and spiders: secrets of the modern-day house hunt

By Rachel Saslow Photography by Thomas Teal March 1, 2023

Portland real estate over the past year had something for everyone in the game—just not all at the same time. Things started off as a seller’s market with bidding wars, waived inspections, and desperate buyers snapping up homes within days. 

“People were buying houses that were like, ‘Sure, the foundation is slowly crumbling and there’s a killer clown in the basement but you’re going to buy it as-is and you’re going to like it,’” says Laura Cross, who began her house hunt in January 2022. She and her partner were outbid on four homes in Northeast Portland, despite offering almost $100,000 over asking price for one.

In the spring and summer, mortgage rates shot up and flipped the whole script. It became more of a buyer’s market where house hunters could actually sleep on their sometimes million-dollar decisions. For that luxury they paid dearly, however, to the tune of a 30-year mortgage interest rate that peaked at 7 percent in November.

“I was in the middle of transactions where people were priced out,” recalls Michelle Thomas Newman, a Realtor with Keller Williams. “They realized the slightest change in interest rates can make the difference of a few hundred dollars on their monthly payment. They were like, ‘I’m out.’” 

 Through 2022, though, the median sale price for a Portland metro-area home still rose: from $509,000 in 2021 to $548,400, even with unpredictable interest rates and as the city grappled with serious issues of homelessness, a record-breaking homicide rate, and rampant property damage and car theft. 

Three intrepid sets of Portland buyers let us tag along on their house hunts this year. Here are their stories.

Bar-Crossed Lovers

Buyers: Laura Cross & Ian Davis / Budget: $600,000 / Purchase Price: $621,000 / Purchase: Three bed, two-and-a-half bath Cully ranch built in 1961

Laura Cross and Ian Davis, with dogs Noel and Pinto

Image: Thomas Teal


iancés Laura Cross and Ian Davis both own busy bars in town (Cross owns Advice Booth, and Davis is part-owner of Bye and Bye and the Sweet Hereafter) and needed a haven. They had been shuttling between her rental in Overlook and his house in Rose City Park for the entire six years of their relationship. “It was getting old,” Davis says.

In January 2022, they got preapproved for a loan and started the hunt, with Cross’s 10-year-old daughter and their two rescue dogs, Noel and Pinto. 

Oh, and Davis’s nine cars. 

A mechanic and metalworker originally from England, Davis had a house wish list that catered to his hobby of fixing up British sports cars: two-car garage, detached workshop, really long driveway. 

“We joked that we were looking for a garage with a house nearby,” Cross says.

Davis also wanted a big basement for storage and a walkable neighborhood in Northeast Portland—not too close to downtown, but not too far, either. 

Cross’s wish list was shorter: “I wanted a kitchen that doesn’t suck, and two toilets.” 

“We joked that we were looking for a garage with a house nearby.” —Laura Cross

They brought their dueling priorities to Chandra Ashford of Think Real Estate. Far from laughing at them for being unrealistic (“some would say delusional,” Cross says), Ashford was an encouraging, patient ally for the couple. It helps that Ashford is Cross’s best friend from college. 

After four rejected offers over the course of the year, they attended an open house in September for a sweet 1961 ranch home on a quiet street in Cully. As they walked through, Cross’s daughter declared that she loved it, which had never happened before. As the gigantic windows, hardwood floors, and original doors and trim revealed themselves, they got even more excited. Finally, they saw the pièce de résistance in the basement: a fully built-out bar. 

It felt meant to be, and it was: they owned the house two weeks later and moved in in October. First, they had the inside repainted and remodeled the kitchen themselves with a quartz countertop custom-made in the exact unique shape of the original 1961 version. Davis has also built a cedar fence around the yard and spiffed up the outdoor shed so it can house his metal workshop. “He has been working so hard to fix things and make them perfect,” Cross says. 

After all, what was Davis’s top item on his real estate wish list? “Make Laura happy,” he says. 

Third Time’s the Charm

Buyers: Hannah & Zoie Brent / Budget: $1.2 million / Purchase Price: $1.15 million / Purchase: Three bed, three-and-a-half bath Craftsman in Eliot

Hannah (left) and Zoie Brent, with their "tiny insurrection baby" and pooch

Image: Thomas Teal


annah and Zoie Brent started toying with the idea of moving to Portland in October 2021. They were about to start a family—their “tiny insurrection baby” would be born January 6, on the one-year anniversary of the dubious events in DC—and Hannah’s parents (who could help with childcare) still lived in her childhood home in Northeast Portland. Then Zoie got a job at a medical device start-up company in Portland, so they listed their home in the Seattle suburb of Kirkland in April 2022. 

With a down payment burning a hole in their pockets, Zoie reached out to Friday and Company after loving its Instagram account and catching Friday’s Calle Holmgren on an episode of House Hunters on HGTV. She appreciated Holmgren’s family expertise.

“It was important to have an agent who knows what it means to have kids in these neighborhoods,” Zoie says. “Especially trying to buy from Seattle, we needed that perspective.” 

“These people are rolling up to houses with suitcases full of cash. It makes it hard to compete.” —Hannah Brent 

The first house the Brents made an offer on was a midcentury-modern home near Reed College. Zoie is hard of hearing, and the open sightlines of that era of construction allow her to easily see her other family members to read their lips. (Lots of hallways and doors, such as in a Victorian, would be a deal-breaker, as would huge, echoey rooms.)

“We were like, ‘This is the house.’ We had already moved in,” Hannah, a nurse, recalls. “We were mentally walking our daughter to the park.” 

They put in an offer ... along with seven other people, some of whom were willing to go hundreds of thousands of dollars over asking price. The Brents were out. A similar story played out with a Dutch colonial on top of Mount Tabor: they were beat out by an all-cash offer from an investment group.

“These people are rolling up to houses with suitcases full of cash,” Hannah says. “It makes it hard to compete.” 

Meanwhile, they were bouncing between Zoie’s parents’ place in Seattle and Hannah’s parents’ basement in Portland, so they were thrilled when Nicole Wear at Friday and Company sent them a listing for a fully remodeled 1910 craftsman that checked every box and more: clear sightlines, fluid indoor/outdoor living with a wall of accordion doors, new ADU and garage, and a cozy Portland feel. 

The catch? It was in Eliot, a neighborhood they had not been considering. Sandwiched between North Williams Avenue and NE Martin Luther King Jr. Boulevard, it’s “as city living as you can get without being downtown,” Hannah says. 

Their hearts sank when they heard there were 10 offers on the home. But the Brents pulled out all the stops—including a “love letter” to the sellers with a photo of their baby and offering $300,000 over asking price—and finally came out on top. (It was the second-highest sale price in Eliot for a single-family home in 2022, and one of the highest ever for the neighborhood.)

They have easily settled into their new neighborhood, especially enjoying their one-mile morning stroller walk that includes a coffee shop, dog park, and playground.

“This house was special,” Zoie says. “The bidding war reaffirmed that it’s the best house we saw in our year of looking.” 


House Hacking at 25

Buyer: Kayla Heine / Budget: $250,000 / Purchase Price: $241,500 / Purchase: Two bed, one-and-a-half bath new-construction condo in Hazelwood 

Kayla Heine in her new kitchen

Image: Thomas Teal


ayla Heine, 25, is willing to sacrifice to build her real-estate empire. She bought her first house in Gresham in summer 2020. She had three roommates all lined up to live with her so the monthly mortgage would pay for itself. 

She offered the primary bedroom to one of her tenants. Heine sleeps in the garage. “With a space heater!” she says. “And it’s a one-car garage, not a huge two-car garage.” She admits the spiders aren’t ideal.

Heine learned about real estate and “house hacking”—generating income from one’s home via tenants—from a six-month self-led gauntlet of education from any free resource she could find, including books, YouTube, podcasts, and networking at open houses. 

“Everyone’s afraid right now because of the interest rates, but you just can’t be afraid,” she says. “I’m going to make so many mistakes, but I’m excited for them—that’s how you learn and grow.” 

“Everyone’s afraid right now because of the interest rates, but you just can’t be afraid. I’m going to make so many mistakes, but I’m excited for them.” —Kayla Heine

To save up enough money for her second down payment, Heine worked overtime at her job at Oregon City’s Benchmade Knife Company. She doesn’t eat out. (Luckily, her boyfriend cooks.) She doesn’t go out to clubs or movies or drive anywhere other than work. In December, she “postponed Christmas.” Her only indulgences are a few streaming subscriptions and her pit bull puppy, Buddy, who entertains her and keeps her busy with his one-hour daily walks. 

Her motto of “short-term sacrifice for long-term success” runs through her mind every day. Her motivation comes from a promise she made to her family. About four years ago, Heine looked her mother in the eye and vowed that she would be a millionaire one day and buy Mom a house. 

Her newest investment is a two-story condo in Hazelwood. She hopes to be permanently done with roommates and cleaning up messes that aren’t hers. She loves that it is close to the MAX line, has brand-new everything and there are two bedrooms—one of which she’ll actually get to sleep in.