The Northern California Downsizing Roadmap
You've owned your home for decades. Downsizing isn't just a move — it's the largest financial decision of your retirement. Here's the step-by-step path, with the money questions answered before they become money mistakes.
The property tax mistake that follows downsizers into the next house
Most people who've owned since the 90s are paying tax on an assessed value a fraction of what the house is worth. Sell, buy the smaller place, and that advantage is gone — the new home gets assessed at your purchase price, and the tax bill can land higher than the one you just left.
Prop 19 is the way out if you're 55 or older, but it only works if you get the order and the deadlines right. This video is the plain-English version, with the actual numbers. Everything on this page (and in the Roadmap PDF) goes one level deeper.
More on the channelSix steps, in the right order
Most downsizing regrets come from doing the right things in the wrong order. This is the sequence I walk clients through.
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Define "what's next" before you touch the house
Closer to the grandkids? Single-level living? Santa Cruz instead of Silicon Valley? A 55+ community? The destination drives everything — the budget, the timing, and whether Prop 19 travels with you. Skip this step and every later decision gets harder.
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Know your real numbers
Three numbers, honestly computed: what your home sells for today (street-level comps, not a Zestimate), what you'll net after commissions, transfer taxes, and capital gains beyond the §121 exclusion, and what the next home costs to own — including the property taxes Prop 19 can dramatically reduce. The Net Proceeds Calculator is step two in ten minutes.
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Build your Prop 19 plan
If you're 55+, you can carry your current property-tax base to the next home, anywhere in California, up to three times — but the rules on timing and price matter. Get this right and you save thousands every year for the rest of your life. Full plain-English guide here.
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Prepare the home — and the decades inside it
Thirty years of living doesn't get boxed up in a weekend. Sorting, donating, estate-sale services, senior move managers, targeted repairs that return more than they cost (and the ones that don't) — a realistic 60–90 day prep plan beats a panicked 2-week one.
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Sequence the sale and the purchase
Sell first, buy first, or bridge? With decades of equity you have options most buyers don't: rent-backs that let you close and then move on your schedule, contingent offers from strength, or bridge financing. We pick the sequence that protects your money and your sleep.
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Close, transfer, and land well
File the Prop 19 base-year transfer, coordinate with your CPA on the gain, and get you moved — with a team (escrow, movers, senior move specialists) that's done this many times. The goal isn't just "sold." It's settled, with your equity working for the next chapter.
The Downsizing Roadmap PDF
The complete roadmap in a printable, share-with-your-spouse format:
- The 6-step timeline, from "thinking about it" to moved in
- The 60–90 day home-prep checklist for longtime owners
- The Prop 19 eligibility checklist
- A net-sheet worksheet — know your walk-away number
- Questions to ask any agent before you list
The PDF downloads on the very next page — no waiting on an email. You'll also get my monthly market note for longtime Bay Area owners; unsubscribe anytime.
Send me the Roadmap
Downsizing FAQ
Should I sell first or buy first?
It depends on your equity position and your tolerance for moving twice. Most longtime owners here have enough equity to negotiate from strength either way — sale contingencies, rent-backs after closing, and bridge financing all keep you in control. It's a math question first and a stress question second; we work through both in a consultation.
Will I lose my low property taxes when I move?
Usually not, if you plan it. Prop 19 lets homeowners 55+ transfer their taxable value to a new primary residence anywhere in California, up to three times. If the replacement costs more than the original sold for, only the amount above a threshold is added to your transferred base — 105% of the original's value if you buy within a year of the sale, 110% in the second year. Buy before you sell and there is no allowance at all: the full difference is added. Timing rules apply — see the full Prop 19 guide.
How bad will capital gains taxes be after 25+ years?
Bigger than most owners expect, but smaller than the worst-case rumors. You get $250K (single) or $500K (married) of gain tax-free under §121, your basis includes documented improvements over the years, and rates depend on income. Run your own numbers, then confirm with your CPA — I'll coordinate with them directly if you'd like.
What if the house needs work after all these years?
Almost every long-held home does. The question is which projects return more than they cost in your micro-market — and which to skip and price around. That's a street-level call, not a rule of thumb, and it's part of every seller plan I prepare.
We're not ready yet. Is it too early to talk?
It's the best time to talk. Most of my downsizing clients start the conversation 1–3 years before they move. Early planning is what makes the Prop 19 transfer, the tax picture, and the prep timeline easy instead of frantic — and there's no cost or obligation to it.
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A What's-Next Consultation covers your home's realistic value, your net after taxes, your Prop 19 savings, and the sequence that fits your life. A conversation, not a pitch.
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