Head East, Young Family

A severe mold problem in their Northeast Portland rental house launched Natalie and Lyf Gildersleeve into the home-buying market in January, 2016. Over the course of three days they packed up everything they owned and left the only home their kids had ever known. They lived with family for one month before finding another rental and starting in earnest to search for a place to call their own.

The Gildersleeves hoped to buy in the Montavilla neighborhood or South Tabor, but found nothing in their price-range (topping out at $380,000) that didn’t require sacrificing space. Their dream home would have a large yard where Juniper, age 6, and Miles, age 3, could play, and the house itself needed to have space for the kids to have their own bedrooms. “We didn’t want to move our whole lives somewhere else, but for a minute we thought we’d have to move out of Portland,” says Natalie Gildersleeve.

MovingTo1Competing with buyers making cash offers that were as much as $80,000 above list price was discouraging and they had friends who were out-bid on homes in inner Southeast as many as 13 times. They worried they’d be stuck buying far from their jobs in Southeast Portland. They had second thoughts on the first home on which they put an offer, an unimproved and unmaintained house near SE 87th Avenue and SE Division Street.

“It was a nice house, but it was the only nice house in the neighborhood,” says Natalie Gildersleeve. They backed out, and despite initial hesitation, took their search farther east.

“Don’t go past 82nd or 92nd,” they heard from people who alluded to sketchy neighborhoods and poor schools. But their 6-year-old daughter, Juniper, already attended Creative Science School, a focus option school on Southeast 92nd Avenue, so they were willing to expand their search to that area. They also ignored advice to buy for location rather than space, opting for room to grow and play rather than imagined resale value years from now.

“Honestly, we got lucky,” says Natalie Gildersleeve. A few months into their search, another buyer backed out of a home on which they had previously made an offer. They were given one hour to decide before the owners re-listed, and despite the stress of finalizing the sale so quickly, they jumped.

Like anyone who has taken a look at the market lately, the Gildersleeves knew to expect challenges in their search, but their overall experience was even more difficult than expected.


The Gildersleeve family’s new home


“Before we started looking, we had this idea that it could be fun and exciting to look at houses, but when it became so intense and cutthroat it became more stressful than anything else,” says Natalie Gildersleeve.



They closed on their home near Southeast Cherry Blossom Drive and Market Street in April. The kids have their own rooms, the house is on a double lot, and they can ride bikes to Juniper’s school. Their new neighbors are much more diverse and “unbelievably nice,” greeting them with fruit baskets and cards of welcome when they moved in. And despite the stress of the search, Natalie Gildersleeve says, “We couldn’t be happier.”

Heather Lee Leap

Heather Lee Leap

Heather Lee Leap’s articles and essays about parenting, family and health have appeared in two dozen regional parenting magazines across North America. When she is not driving her three daughters to soccer practice and music lessons, she looks for new ways to supplement their education. Heather writes from her home in northeast Portland.
Heather Lee Leap

Latest posts by Heather Lee Leap (see all)