Katrina Hanson, left, and Maya Brodkey in Oakland, Calif., where they searched for a new two-bedroom home. Jason Henry for The New York Times

Maya Brodkey and Katrina Hanson left Oakland, Calif., in 2020 by choice, but not by preference. When the pandemic cost Ms. Hanson her acupuncture practice, they knew that sizing up from their one-bedroom apartment to something nicer in the area couldn’t be done on Ms. Brodkey’s salary alone.

So they ventured 275 miles north to more affordable Eureka, Calif., where Ms. Brodkey worked as an English teacher and Ms. Hanson as a services administrator at a college, and began saving money. Eventually, they bought a home there. But their love of Oakland lingered. Every few weeks, they’d make the five-hour drive from Eureka to stay in touch with friends.

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“All of our people are here,” said Ms. Brodkey, 35. “You live in a place for 10 years, especially when you’re in your 20s, and you build some really strong relationships.”

Ms. Brodkey, who grew up in Santa Cruz, Calif., met Ms. Hanson when both were freshmen at The Evergreen State College in Ms. Hanson’s native Washington State. They lived in what Ms. Brodkey called the “social action” dorm — “do-gooders, you know?” she said with a chuckle — and their friendship became a romance the next year. After graduating, both worked in AmeriCorps, a public-service program, before moving on to new jobs.

By 2024, the couple felt ready to re-enter the fickle Oakland housing market, where properties are often deliberately underpriced in order to incite bidding wars.

“It’s a trend in the Bay Area, sadly,” said Carol Koback, the Compass agent who worked with the couple.

Because their Eureka home hadn’t appreciated much in value, Ms. Brodkey and Ms. Hanson decided to hunt in Oakland without selling it. But the $500,000 loan they qualified for wasn’t enough to make a dent, so they went back to saving. By spring 2025, they had enough to qualify at $600,000 and had $50,000 to $60,000 for a down payment. And they needed to thread a needle when it came to the calendar and their wants.

“Because Maya’s a teacher, we could only move in summer,” said Ms. Hanson, 36. And with two rescue dogs and two cats, they needed a place with some outdoor space.

They wanted two bedrooms, good light, enough kitchen or dining space to host friends and family, and storage for their outdoor gear. “Every place we walked in, it was like, ‘How many people could we fit for Shabbat?’ Because Shabbat dinner was the big thing,” Ms. Brodkey said.

At their price range, they’d need to manage their expectations. “They were determined,” Ms. Koback said. “There wasn’t a ton of money, but determination they had.”

Among their options:

No. 1

Brick Loft Condo in Fruitvale

Jason Henry for The New York Times

This two-bedroom, one-bath, 1,232-square-foot condo in a former mattress factory oozed charm, and the tiny gated complex that contained it was almost enveloped by the lush garden in the common area. The industrial aesthetic included a big open kitchen and living room, soaring ceilings, exposed brick and concrete floors. One bedroom was fully walled off, though skylights provided ample light throughout. The only outdoor area was a small gravel patio in front, and storage space would be tight. The homeowners’ association was embroiled in a legal dispute that could complicate a sale, but with the condo listed at $419,000, there would be room for improvements. Annual taxes were about $9,200, and there was a $572 monthly HOA fee.

Sparker Red

No. 2

Craftsman Bungalow With a Yard

Jason Henry for The New York Times

This two-bedroom, one-bath bungalow from 1922 had only 986 square feet, but it was buttressed by a backyard that featured a raised deck, a second sitting space and redwood planter boxes. The house had some original features and had been nicely updated, with its layout concentrating the square footage in the living and dining area. A bonus space off the kitchen had a washer and dryer. Ms. Brodkey liked the location, in the Maxwell Park neighborhood with a close friend only two blocks away. It was situated near busy Oakland thoroughfares, and although it was listed at $395,000, Ms. Koback warned that the sellers were actually aiming for $600,000. Annual taxes would be about $10,000.

Compass

No. 3

Two-Bedroom With Luxury Touches

Jason Henry for The New York Times

At 736 square feet, this two-bedroom, one-bath house from 1920 was the smallest place the couple considered, but the most upscale. Located in Maxwell Park near Mills College, where Ms. Brodkey earned her masters’s degree in education, the home was updated, including with a six-burner Wolf range, a Liebherr refrigerator, a custom tile kitchen backsplash by a local artist, and an open floorplan throughout. The living room had a wood stove and glass doors that opened to a landscaped yard with space for pets and entertaining, a cute detached shed with an office setup, and fruit trees. The $625,000 price required re-approval from their lender, and they were warned that a bidding war was likely. Annual taxes would be about $10,200.

Red Oak Realty

Find out what happened next by answering these two questions:

Which Would You Choose?

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Brick Loft Condo in Fruitvale

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Craftsman Bungalow With a Yard

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Two-Bedroom With Luxury Touches

Which Did They Buy?

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Brick Loft Condo in Fruitvale

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Craftsman Bungalow With a Yard

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Two-Bedroom With Luxury Touches