If your parents bought their house decades ago, selling now could cost the family $300,000 or more in capital gains tax. Holding it until death, on the other hand, can wipe that tax out completely through the stepped-up basis. Both are true, and that’s what makes the decision so hard for many families.
To make it real, I walked through the numbers for a typical Mountain View home. On one road, Mom sells the house and pays capital gains tax on decades of appreciation. On the other, the family holds the house, and when it’s inherited, its tax basis resets to its value at the time of death. For married couples in California, the community property rule can allow the whole house to get that step-up when the first spouse dies, not just half.
But holding isn’t automatically the right answer. Care is expensive. According to the CareScout 2025 Cost of Care Survey, the national median for assisted living is about $6,200 a month, and a private room in a nursing home runs about $10,800 a month. Families need a plan to pay for care and still keep the step-up.
Some shortcuts can backfire, too. Putting the house in the kids’ names, for example, can cost the family the stepped-up basis entirely. Trusts and the estate tax also play a role, and there are rules that may let a homeowner keep the $250,000 home sale exclusion even after moving into a care facility.
The right choice depends on your family’s health, finances, timeline, and goals. Before anyone decides, it helps to ask the right questions and run the real numbers instead of relying on rules of thumb.
I’m not a CPA or attorney, so please confirm your own situation with your tax and legal advisors. But if you’re weighing whether to sell now or hold, I’m happy to help you think it through.
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From the Bay Area Wayback Machine
The Oakland Hills Firestorm (October 20, 1991)
What started as a small brush fire in the Berkeley Hills on October 19 was thought to be under control, but it rekindled shortly before 11 a.m. the next morning. Pushed by Diablo winds gusting up to 65 mph, the Oakland firestorm raced through the Oakland Hills and into southeastern Berkeley. Over three days, it burned about 1,520 acres, destroyed more than 2,800 homes and hundreds of apartment and condominium units, and claimed 25 lives. The disaster led to lasting changes in fire safety across the region, including standardized fire hydrants, upgraded emergency radios, and better wildland gear for firefighters.
This Week in Silicon Valley
Audit Finds Hidden Fees Hinder Palo Alto’s Affordable Homeownership Program
A new audit of Palo Alto‘s Below Market Rate Housing Purchase Program found that a lack of transparency around homeowners association fees can put a strain on the low-income buyers it’s meant to help. The program includes 247 active affordable ownership homes, most built before 2000. The audit flagged HOA dues, special assessments, and major maintenance costs as concerns, noting that the city has no consolidated system for tracking them.
Officials also raised concerns about the program’s aging homes. Some of the earliest units, built in the 1970s, could leave the program by 2033, and no new homes were added in the 2010s. Recommendations include making HOA and maintenance costs clearer to buyers before they purchase, tracking complaints, and monitoring turnover and vacancies.
The city’s Policy and Services Committee unanimously approved the audit’s findings on October 13, though the full City Council may not take up policy changes until next year.
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See the Live Sales Data →Engelbert Humperdinck: The Celebration Tour 2026
Date: Wednesday, October 21
Time: 7:30 pm
Location: California Theatre, 345 South First Street, San Jose
Spend a romantic evening with one of music’s most beloved crooners as Engelbert Humperdinck brings his Celebration Tour to the historic California Theatre. Settle in for his classic hits and timeless love songs, and let that unmistakable voice carry you back to some of your favorite memories.
HAPAG: Elevated Filipino Kamayan Dinner
Date: Friday, October 23
Time: 6:00 pm – 9:00 pm
Location: Wheelhouse, 1173 Lincoln Avenue, San Jose
Gather around the table for a joyful kamayan-style feast, where Filipino dishes are shared family-style and enjoyed by hand. Barya Kitchen serves up an elevated menu paired with creative cocktails and mocktails, while live acoustic music from Domryn and Filipino storytelling turn dinner into a warm, memorable celebration of culture.
Witches & Warlocks Wine Stroll
Date: Friday, October 23
Time: 6:00 pm – 9:00 pm
Location: Downtown Los Altos
Dust off your pointy hat and grab your friends for a spooky, spirited evening in charming Downtown Los Altos. Stroll from stop to stop sampling wines from local wineries, enjoy live music from upbeat bands along the way, and soak up the Halloween magic of one of the area’s favorite fall traditions.
Tasting Tour di Eataly
Date: Sunday, October 25
Time: 11:00 am – 12:30 pm
Location: Eataly Silicon Valley, 2855 Stevens Creek Boulevard, San Jose
Treat yourself to a little taste of Italy without leaving San Jose. Eataly’s experts lead you through the marketplace, sharing the stories behind Italy’s favorite foods while you sample your way from counter to counter. It’s a delicious way to spend a Sunday morning and discover new favorites to bring home.
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Senior Friendly Homes in Silicon Valley South
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