After bouncing from the East Coast to the Midwest, a job offer pulled Kevin McGregor and Monika Johnson farther west, to Oakland.
The two met in their early 20s through a group of friends organizing bike rides around Washington, D.C., where they were living after college graduation. The couple later headed to Michigan, where Johnson attended business school. After she graduated in 2019, a job in California beckoned.
Now 36, both have careers in quintessential Bay Area industries — Johnson works in finance for a wine company, while McGregor works in account management in the clean energy sector.
In time, the couple established a tight-knit community in Oakland’s Glenview neighborhood, just north of Highway 580 and southeast of Piedmont, regularly meeting up with friends for “wine Wednesdays.”
Four years into renting a two-bedroom, one-bathroom duplex, they felt it was time to buy.
“We wanted to put down some roots,” Johnson said. Staying close to friends was a high priority.
“Our community there, the Glenview crew, was something we didn’t want to lose,” McGregor said. “Neighborhood feel was super important to us.”
Beyond that, they also wanted to be near trails, and have a big backyard for their 75-pound mixed-breed dog, Luca.
“One of the things we’ve enjoyed about Oakland is that you have access to the city and great food and culture, and you’re also a 10-minute drive to fantastic hiking trails,” Johnson said. “It feels like we’re getting the best of both worlds.”
With a budget of $1.1 million, they were looking for a home to which they could add value.
“We wanted an opportunity to bring something with good bones more up to date,” Johnson said. “Lots of homes in Oakland are either recently flipped or need a lot of work. We considered taking on a bigger project, but ultimately we wanted to still live in it while we did renovations.”
Given that they were looking in the Oakland Hills, they were concerned about insurability, too. They enlisted the help of Cheyenne Ward, a Berkeley-based broker with District Homes, who used the term “Oakland trifecta” to describe what they were looking for — something that wasn’t at high risk of landslide or liquefaction, or on a fault line. He also helped them line up insurance and financing before they even made an offer.
Here were the options they considered:
A multi-level home with a terraced backyard
This five-bedroom, two-bath home, built in 1947, had been owned by the same family for the last 70 years. It had 2,228 square feet, original wood paneling, large windows and a fireplace. But the kitchens and bathrooms were locked in a 1980s time capsule.
The backyard, terraced and dotted with fruit trees and patios, was the highlight. It was listed at $998,000.
An outdated kitchen, but with forest and bay views
This three-bedroom, two-bath, 1,785-square-foot house was built in 1942 in Lincoln Highlands, a residential neighborhood just south of Joaquin Miller Park. The open living and dining room featured curved walls, an exposed beam ceiling and refinished hardwood floors. The kitchen and bathrooms still retained most of their 1940s features.
Multiple rooms featured sweeping views, stretching from the Alameda Naval Base to Mount Tamalpais. The home featured decks on the top and bottom floors, looking out into a woodsy backyard. It was listed at $998,000.
A historic Tudor charmer just down the hill
A bit farther down the hill, this 1931 Tudor-inspired home included three bedrooms and two baths, measuring 1,884 square feet — all just steps away from Dimond Park. The living room featured a fireplace frame with a gas-insert heater, and the kitchen had recently been repainted and updated with new quartz countertops. The backyard was smaller than others they toured, with a small patio, pebble pathways and a shed for extra storage. It was listed at $849,000.
Which one did they go with?
McGregor and Johnson put in an offer of $1.1 million on the multi-level home with the terraced backyard, but were outbid. Looking back, they’re glad they didn’t end up with a five-bedroom home. “Less to clean,” Johnson joked.
After touring the Tudor, they discovered it needed more work than they wanted to do — but the listing agent, Deidre Joyner, pointed them to her other listing up the street — the one with a woodsy backyard.
Initially, Johnson and McGregor thought the home would be out of their price range, but they noticed that it hadn’t gone into “pending” status even after the original offer deadline Joyner set. They quickly set up a tour and loved the interior details, like the well-maintained floors and curved walls.
“It felt like a place where we could kind of carry on the legacy of folks who had taken good care of it before,” McGregor said.
Ward, knowing that homes tend to be priced low to get multiple offers, advised the couple to submit an offer over asking. After getting an estimate on how much work would be required to bring the house into good shape, Ward also advised them to make their offer noncontingent on financing or insurance, both of which they’d already squared away.
Two days after their tour, while driving up to Lake Tahoe for a ski weekend with friends, McGregor and Johnson submitted an offer of $1.1 million. The next day, they were on the chairlift when they got a call from Ward. They’d won the house.
Monika Johnson and Kevin McGregor in the dining room of their new home in Lincoln Highlands in Oakland, Calif., on Tuesday, June 17, 2025. The first-time homebuyers bought their 1942 home in April. (Jane Tyska/Bay Area News Group)
It turned out that their offer had come in $50,000 lower than another on the table, but the competing offer was contingent upon inspections and securing an insurance policy. That made the sellers nervous.
“We had already done all of that,” Ward said. “We got a discount just from doing our homework in advance.”
They also say they benefited from timing — President Donald Trump’s trade wars this spring gave a number of buyers pause. That may have given those still on the market, like McGregor and Johnson, an edge.
“We were willing to stomach a bit of uncertainty,” McGregor said. They say they’re glad they didn’t go beyond their initial budget, despite hearing from loan officers who told them they could just refinance if rates go down. The couple didn’t want to take any chances on that front.
“We made a decision we knew we could live with for a long time,” Johnson said.
McGregor and Johnson moved into their new home this spring and have already welcomed friends for dinner, neighborhood walks and dog playdates.
The first home project? Buildiing a fence, so Luca can run free in the backyard. The kitchen renovation will wait, for now.
More chapters in our home search series:
• First-time East Bay home buyers with a $750,000 budget and no agent
• Seeking good schools, nature and ‘a feeling of privacy’ on the Peninsula for $3.5 million
• Downsizing retiree wants a $1.2 million home near San Jose