Stay, Downsize, or Move?
A free three-minute check for longtime Bay Area homeowners and the families helping them. See which path fits best, and what each one would really cost you or free up, before a costly mistake makes the decision for you.
⭐️⭐️⭐️⭐️⭐️ 54 five-star Google reviews · 23 Years Helping Bay Area Families
Certified Senior Advisor (SCSA®) · Certified Aging in Place Specialist (CAPS®)
Take the Three Minute Quiz
Free 3-minute decision check
Stay, downsize, or move? Find out which one costs you the least.
For longtime Bay Area owners, this is usually the biggest money decision of retirement, and the wrong call can cost six figures in taxes, remodeling, or years of higher living costs. Answer a dozen quick questions and see all three paths side by side, with a rough dollar figure for what each one would cost you or free up.
- Takes about three minutes, one tap per question
- Works whether you're planning for yourself or helping a parent
- Your answers stay private
- ★★★★★ 54 five-star Google reviews
- Certified Senior Advisor
- Certified Aging in Place Specialist
- Affiliate Member, Professional Fiduciary Association of California
The most expensive mistake longtime owners make
After decades in the same Silicon Valley home, most of your net worth is probably sitting in the house. That's exactly why stay, downsize, or move isn't really a lifestyle question. It's a money question, and the mistakes are expensive and hard to undo: selling without a plan for capital gains, buying a replacement home without filing for Prop 19, pouring six figures into a remodel the house will never pay back, or leaving the kids a tax bill they didn't see coming.
The good news is that most of those losses are avoidable with the right order of moves. Federal law lets a homeowner exclude up to $250,000 of gain on the sale of a primary home, or $500,000 for a married couple filing jointly. California's Proposition 19 lets owners 55 and older carry their property tax base to a replacement home anywhere in the state, up to three times, if the new home is bought within two years of the sale. And heirs generally receive a stepped-up cost basis, which can make holding the house the right call for some families.
Signs it's time to run the numbers
- You've owned the home 20 years or more and it's worth several times what you paid
- The stairs, the yard, or the upkeep take more out of you every year
- Insurance, repairs, and utilities are eating into your monthly budget
- The kids or grandkids live somewhere else and you'd like to be closer
- A spouse has passed and you're deciding what to do with the house on your own
- You're 55 or older and haven't looked at how Prop 19 applies to you
The quiz above weighs all of that and puts a rough dollar figure on each path, so you can see what's at stake before you talk to anyone.
of adults 50+ want to stay in their current homes as they age
Source: AARP, 2024
of U.S. homes have a step-free entry, single-floor living, and wide halls and doorways
Source: Harvard Joint Center for Housing Studies
typical cost of a universal-design bathroom remodel in San Francisco
Source: 2025 Cost vs. Value Report
How to choose between staying, downsizing, and moving
I've spent 23 years helping Silicon Valley families with this exact decision, and the ones who come out ahead aren't the ones who guessed right. They're the ones who put real numbers next to each option before they committed to any of them. Here's how I'd walk through it.
Start with the money, not the house
Before you think about square footage, find out three numbers: what the house would sell for, your cost basis (what you paid plus improvements), and your current property tax bill. Those three tell you how much capital gains tax is in play, how much the home sale exclusion covers, and what you'd give up by losing your Prop 13 base. A CPA and a good listing agent can get you there in an afternoon.
Staying: price the house you'll need, not the one you have
Staying can be the smartest move, especially if your heirs will benefit from a stepped-up basis. But be honest about what the house needs to work for the next ten years. The 2025 Cost vs. Value Report puts a universal-design bathroom remodel in San Francisco at about $52,000 and a midrange primary suite addition at about $207,000. And according to Genworth and CareScout, the national median for a full-time home health aide was about $77,800 a year in 2024. Add those up before you decide staying is the cheap option.
Downsizing: use Prop 19 before you lose it
Downsizing close to home keeps your doctors, friends, and routines while turning equity into cash you can use. If you're 55 or older, Prop 19 lets you take your low property tax base with you, but only if you file for it and buy the replacement within two years of selling. Miss that window and your tax bill resets to the full rate on the new home.
Moving away: run the monthly math
Moving closer to family or to a lower-cost area can change retirement math more than anything else. Inside California, Prop 19 can still carry your tax base. Out of state, it can't, so compare the new property tax, insurance, and cost of living against what you'll free up from the sale.
Don't forget the kids
Holding the house for heirs isn't the automatic win it used to be. Under Prop 19, a child generally keeps the parents' low tax base only if they move in as their primary residence, and only up to a cap. The Board of Equalization currently lists that cap as the existing taxable value plus $1,044,586. If the kids plan to rent it out or sell, the property tax resets. That's a conversation to have with an estate planning attorney before anyone decides.
Questions about staying, downsizing, or moving
It comes down to three things: whether the house can work for you as your needs change, what staying really costs each year, and how much equity selling would free up after taxes. If the house needs major changes like a first-floor bedroom, or the costs are squeezing your budget, downsizing often wins. If the house already works and your heirs would benefit from a stepped-up basis, staying can be the better money move.
Federal law lets you exclude up to $250,000 of gain, or $500,000 for a married couple filing jointly, if you owned and lived in the home for at least two of the last five years. Gain above that is taxed at federal capital gains rates, and California taxes it as ordinary income. On long-held Bay Area homes the taxable gain can be large, so have a CPA run the numbers with your real cost basis and improvements.
If you're 55 or older, Prop 19 lets you transfer your property tax base to a replacement home anywhere in California, up to three times, as long as you buy within two years of selling. If the new home costs more than the old one sold for, part of the difference is added to your tax base.
No. The base-year transfer only works for a replacement home in California. Out of state, you'll pay that state's property tax on the new home, so factor it into the move-away math.
A surviving spouse who hasn't remarried can generally still claim the full $500,000 exclusion if the home is sold within two years of the spouse's death. In California, a home held as community property also usually gets a full stepped-up basis at the first death. Confirm both with a CPA before you sell.
Heirs generally receive a stepped-up cost basis, which can erase decades of gain. But under Prop 19, children keep the low property tax only if they move in as their primary home, and only up to a cap. If they would rent it out or sell, the math often changes. An estate planning attorney and a CPA should weigh in before you decide.
It ranges from a few thousand dollars for grab bars, railings, and better lighting, to roughly $52,000 for a universal-design bathroom, to over $200,000 to add a first-floor primary suite, based on the 2025 Cost vs. Value Report for San Francisco.
A Certified Aging in Place Specialist (CAPS) is trained through the National Association of Home Builders to assess how well a home will work as its owners age and to plan changes like zero-step entries, wider doorways, and accessible bathrooms. It's especially useful when you're weighing a remodel against a move.
Work With Sebastian
"I help Long-Time Bay Area Homeowners make their next move their best one yet."
-Seb Frey, REALTOR®