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Triple the home, half the price: A boomer cashed out of California for a better deal in Oregon

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Triple the home, half the price: A boomer cashed out of California for a better deal in Oregon


  • Jeremy Smith sold his 2 California houses in 2021 when demand for homes surged and mortgage rates fell.
  • Smith and his wife moved to Oregon, where they found a much larger home for half the price.
  • While Smith misses California, he’s surrounded by ex-Californians in his Portland suburb.

As a businessman, Jeremy Smith never liked the term “downsizing.” When a CEO uses it, it doesn’t tend to be good news.

When it came to retirement, though, Smith and his wife were excited to eventually trade their house in San Ramon, California, 35 miles east of San Francisco, for a smaller, more affordable home to grow old in.

But the couple ultimately opted to upsize their living space — if not their mortgage payments. They ended up leaving California behind and buying a much larger — and much cheaper — place in Oregon.

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Smith, who founded a food brokerage company called LaunchPad, wasn’t quite ready to retire in 2021. But watching home values in California skyrocket in 2021, he decided it was time to sell. First, he listed his South Lake Tahoe vacation home, which he’d bought just six years prior for $540,000. The house sold the same day in April 2021 for $1.2 million, all cash and over the asking price.

The sale convinced him to put their primary East Bay house on the market, too. That home, which Smith bought in 2010 for $600,000, sold for $1.5 million.

At first, the couple considered retiring to someplace in Southern California, like Malibu or Manhattan Beach. But their home sales suggested to him they needed to buy their next place outside of California’s hyper-competitive, extremely expensive market.

“I felt like it’s one of those things where you throw a quarter in a slot in Vegas, and it pays $1 million, and you don’t stay at the casino. You get that money, you get the hell out, and you go home so you’re not tempted to spend it,” Smith said.

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Smith’s wife, a native Oregonian, pushed for Portland. So they decided on the small city of West Linn, a quiet suburb just south of the city.

When they realized how much more affordable Oregon was, they opted for a home almost three times the square footage of their San Ramon house, but at half the price. They bought the place for $750,000 in June 2021, while mortgage rates were still low.

“I didn’t realize the tremendous cost of living savings that we would get by moving to Portland,” Smith said. “We wound up getting more for a lot, lot less, which allowed us to invest back into the stock market.”


Jeremy Smith and his wife, Mary Jo, in their kitchen.

Jeremy Smith and his wife, Mary Jo, sold their primary home in San Ramon, California, for $1.5 million at the peak of the market in 2021.

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Courtesy of Jeremy Smith



A community of Californians

Despite loving the Portland area in many ways, Smith misses California. He yearns for warmer weather, sunshine, ocean views, and living closer to his three children and grandchildren. He says he visits about four times a year to see his kids and doctors.

“I miss the hell out of California,” he said. “Yes, it’s expensive, but it’s a magical place.”

Still, he loves being surrounded by Oregon’s many rivers and Lake Oswego, where his wife kayaks regularly with her friends. And the food is excellent in Portland, he added.

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And while Smith may have left California, he’s still surrounded by Californians. He estimates that 12 of the 14 homes in his gated neighborhood are owned by people who moved to Oregon from California. Many came to Portland for a more affordable retirement, and some still have homes in the Golden State.

These days, he spends his time walking his two French bulldogs, eating out with friends, and chatting with neighbors. “It’s nice to be able to joke around and talk about all the fun stuff in California,” he said.

But he’s still adjusting to some of Oregon’s quirks.

“I’ve never seen so many damn beards in my life,” he joked. “And you’ve got to get used to flannel shirts.”

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Do you have a story to share about home selling, buying, or moving? Contact this reporter at erelman@businessinsider.com.





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OPB’s First Look: Town hall follows power outages

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OPB’s First Look: Town hall follows power outages


OPB’s First Look: Town hall follows power outages – OPB

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Public asked to help find missing 2-year-old Armani Andrews in Portland

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Public asked to help find missing 2-year-old Armani Andrews in Portland


Oregon officials asked the public to help find a two-year-old boy who went missing from Portland last Wednesday, June 17.

The Oregon Department of Human Services, Child Welfare Division, is asking the public to help find Armani Andrews and call 911 or local law enforcement if they believe they saw him.

Armani is believed to be in danger and is suspected to be in Portland, around any of the following areas: Rose Haven, Multnomah County Central Library, or Southeast Portland around 82nd-103rd.

Armani is a two-year-old Black/mixed race baby. He is about 24 inches tall, he has brown hair, brown eyes, and his weight is unknown.

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If contacting Portland Police Bureau about Armani, reference the case number: #PP185430

The report number for Armani with the National Center for Missing and Exploited Children Report is: 2093182

ODHS said in a statement when a child is missing, they may be in significant danger and the department “may need to locate them to assess and support their safety.”

KATU News reached out to ODHS to clarify whether there is a custody aspect to the missing child’s case. The department said they are unable to provide that information.

Armani Andrews with Mother Rashonda Andrews/ODHS photos

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You can report suspected child abuse to the Oregon Child Abuse Hotline by calling 1-855-503-SAFE (7233). The toll-free number allows anyone to report abuse of any child or adult to the Oregon Department of Human Services, 24 hours a day, seven days a week and every day of the year.

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KATU News included photographs of Armani to help the public identify and find him.



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The Cost of the Crackdown: How Trump’s immigration enforcement affects Oregon

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The Cost of the Crackdown: How Trump’s immigration enforcement affects Oregon


President Donald Trump campaigned on carrying out what he called the largest deportation operation in American history.

After taking office, his administration quickly ramped up immigration enforcement. Border czar Tom Homan also pledged to focus on so-called sanctuary cities, including Portland. According to the U.S. Department of Homeland Security, more than 675,000 people were deported in 2025, while the agency says more than 2 million people “self-deported.”

READ ALSO | Supreme Court hands Trump immigration wins, but birthright citizenship might be different

In Oregon, state data shows state and local agencies experienced a 265% increase in immigration-related requests from federal authorities last year.

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So what does that mean for Oregon’s economy?

The state’s chief economist says the effects are beginning to emerge.

Carl Riccadonna, Oregon’s state economist, said immigration enforcement actions are influencing consumer spending and activity across several key industries, though the state cannot yet quantify the overall impact.

“What we’re seeing in terms of immigration action is playing out in either consumption patterns, which we’ve seen in some communities, or in industrial or sectoral activity,” Riccadonna said. “This does then have implications for how we are reading the overall macroeconomy and putting together that revenue forecast.”

Portland police officers walk outside the U.S. Immigration and Customs Enforcement facility on Thursday, Jan. 8, 2026, in Portland, Ore. (AP Photo/Jenny Kane)

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Riccadonna said the effects extend beyond agriculture, an industry that has historically relied on immigrant labor.

“We have certainly, in sector-by-sector analysis, we’re hearing evidence of impacts from immigration in consumption numbers, so retail, groceries, those sorts of things,” Riccadonna said. “There are also significant impacts in the retail sector and leisure and hospitality, restaurants and construction, important legacy industries of Oregon like timber, forestry … and manufacturing has a very large footprint as well.”

While the state is seeing those trends, Riccadonna said economists cannot yet calculate exactly how much immigration enforcement has affected Oregon’s economy.

“We haven’t done an exercise to say, well, this is what the forecast would have been otherwise. We don’t produce counterfactuals … but there’s plenty of anecdotal evidence from the cherry harvest this past summer and stresses elsewhere throughout those specific sectors,” he said.

National data offers additional context.

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According to the nonpartisan Congressional Budget Office, the recent immigration surge — which the report says mostly comprises immigrants who were not lawful permanent residents, were not eligible to apply for lawful permanent residency based on their current status, and were not admitted on a temporary basis under the Immigration and Nationality Act — generated approximately $10 billion in state and local tax revenue in 2023. During that same period, governments spent nearly $19 billion on services such as schools, shelters and border security.

A damaged car is seen as law enforcement officials work the scene following reports that federal immigration officers shot and wounded people in Portland, Ore., Thursday, Jan. 8, 2026. (AP Photo/Jenny Kane)

A damaged car is seen as law enforcement officials work the scene following reports that federal immigration officers shot and wounded people in Portland, Ore., Thursday, Jan. 8, 2026. (AP Photo/Jenny Kane)

The Congressional Budget Office also projects the immigration surge that began in 2023 will increase the U.S. labor force by approximately 5.8 million people by 2034 and boost the nation’s economic output by nearly $9 trillion over the next decade.

Riccadonna said Oregon expects to gain a clearer picture of the economic effects as more tax and revenue data becomes available.

This story is part of KATU’s “The Cost of the Crackdown” special, which examines how increased immigration enforcement is affecting Oregon, from businesses and workers to the state’s broader economy.

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