Selling a Home Over $10 Million in Hillsborough, California: The 2026 Guide

Selling a home over $10 million in Hillsborough is not a bigger version of a normal sale. It's a different market with its own rules.

The town-wide numbers say homes sell fast and above asking. The top tier runs on different math. Estates at this level are priced with few true comparables, reach a small and global pool of buyers, and carry tax and withholding bills that can run into the millions.

This guide covers the $10 million tier: the 2026 market at the top, how estates are priced and marketed, tax math, trust sales, privacy and timing. It draws on public records and press coverage, including Villa de Verano, which sold for $70 million in August 2026, the highest sale recorded in Hillsborough. Jenn Gilson of Golden Gate Sotheby's International Realty was the listing agent.¹

For staging and pricing basics, see how to pick the best Realtor for selling a home in Hillsborough and this guide to selling a luxury home in Burlingame or Hillsborough.

What the $10 Million Market in Hillsborough Looks Like in 2026

Hillsborough's Town-Wide Numbers vs. the Top Tier

According to Redfin's Hillsborough housing market data, the median sale price was $6,407,291 as of July 2026, up 25.3% year over year.² Forty-one homes sold in that period, and the median home sold in 13 days.² Homes sold for 104.9% of list price on average, and 65.1% sold above list.²

Zillow's Home Value Index put the typical Hillsborough home value at about $5.37 million as of July 31, 2026.³

Those numbers describe a fast town, not a 12-acre estate.

The 2026 Benchmark: Villa de Verano in Hillsborough

The clearest marker for the top of the market this year is Villa de Verano at 3000 Ralston Avenue. The Lake Como inspired estate sold for $70 million in August 2026, the highest sale recorded in Hillsborough.¹ ABC7 also called it the highest Northern California home sale of 2026.¹

National press followed. The Wall Street Journal reported the $70 million Hillsborough sale, and the San Francisco Chronicle and San Francisco Business Times covered it too.⁴ While the estate was on the market, Robb Report ran a feature on it.⁴ That placement puts a property in front of buyers who never scroll the local MLS.

How Hillsborough Estates Over $10 Million Are Priced

Pricing at this level is a strategy, not a formula.

Why Comparables Run Thin at the Top in Hillsborough

Forty-one Hillsborough homes sold in the three months ending July 2026, with a median near $6.4 million.² Once a seller is above Villa de Verano's $70 million, there is no higher recorded Hillsborough sale to point to at all.¹

So a price at this tier is built from the property's own facts:

• Land: acreage, usable flat area, views, privacy and street
• Improvements: square footage, age, quality of construction and recent work
• Rarity: architecture, history and features buyers can't find elsewhere in Hillsborough
• Condition and paperwork: permits, inspections and plans on file

Land Value in Hillsborough Pricing

At this level, a buyer may be paying for the land as much as the house, especially one who plans to renovate or build new. A good pricing analysis values the lot and the improvements separately, so you know what each buyer type is paying for.

Over a decade ago Jenn's family founded Gilson Development, which remodels and custom-builds homes on the Peninsula and in Silicon Valley, and she often brings buyers and developers together.⁵ Her listing at 2265 Ralston Avenue, priced at $19,950,000, is marketed as a planned new estate in Lower North Hillsborough: a 5,132 square foot main residence on a lot of about 22,752 square feet.⁶ That's a price built on land, plans and a finished vision, not on a nearby comp.

Pricing as a Strategy in Hillsborough

The list price is also a marketing decision. It shapes who calls and how the press frames the story. Before you settle on a number, decide:

• Your floor, agreed with your CPA and attorney before launch
• A quiet start or a full public launch (see the privacy section below)
• Which buyers you're pricing for: local families, relocating executives or global buyers

Price-Change Discipline for Hillsborough Estates

Price changes happen across Hillsborough. Redfin showed 14.9% of Hillsborough homes with price drops around July 2026.² At the top tier, the way a change is handled matters as much as the number:

• Set your first price review date before launch, not after interest fades.
• Treat any change as a relaunch, with fresh outreach, not a quiet edit on the MLS.
• Track who toured and who asked for documents. Call them first after any change.

How Jenn Gilson Markets Hillsborough Estates Over $10 Million

The Crosby Estate in Hillsborough: Two Owners, One Agent

The Bing Crosby Estate sold for $25 million in June 2025, its first time on the market in more than 60 years.⁷ Jenn represented that sale.⁸

The next owners renovated the landmark and hired Jenn to relist it in spring 2026, now as 1200 Armsby Drive at $28,995,000.⁸ Two consecutive owners of one Hillsborough estate chose the same listing agent.

A Case Study in $10 Million Marketing

Jenn's approach at this tier rests on reach and discretion. Her estates get press placement: Villa de Verano was covered by The Wall Street Journal, and Robb Report featured it while it was listed.⁴ Video does heavy lifting too. The Bing Crosby Estate video was at one point Sotheby's International Realty's most-viewed video, with around 18 million views.⁹

The Sotheby's network carries that reach overseas. Her listings have been featured by other Sotheby's International Realty affiliates abroad, including India Sotheby's International Realty's Home & Art magazine and LIV Sotheby's International Realty, and her Hillsborough "Western White House" listing was covered by The National in Abu Dhabi.¹⁰ Her marketing partner, STOYC, runs local and global campaigns across social, web, media and email.⁵

Reach doesn't mean every seller wants exposure. An Atherton seller wrote on Zillow in 2023: "She had a strategy of private listing".¹¹ Jenn is lead agent and personally handles all communication with clients and agents, which keeps a sensitive sale in one set of hands.⁵

The Cost of Selling a $10 Million Home in Hillsborough: Taxes and Withholding

This section is general information, not tax advice; talk to your CPA and attorney before you list.

Transfer Tax in Hillsborough

San Mateo County charges a documentary transfer tax of 55 cents per $500, which works out to $1.10 per $1,000 of value. You can check the rate on the county's documentary transfer tax page.¹² Title company guides show the county tax is customarily paid by the seller in San Mateo County.¹³

Title company guides also list a Hillsborough city transfer tax of $0.30 per $1,000.¹³ We could not confirm that rate in the Town's own code, so confirm it with your escrow officer.

Here's simple arithmetic on the published rates for a hypothetical $12 million Hillsborough sale, with San Francisco for contrast.¹³

Transfer tax item (illustration only)	Rate	On a $12,000,000 sale
San Mateo County documentary transfer tax	$1.10 per $1,000	$13,200
Hillsborough city transfer tax (confirm with escrow)	$0.30 per $1,000	$3,600
Total in Hillsborough	$1.40 per $1,000	$16,800
Same price in San Francisco, city tax only (for comparison)	$55 per $1,000	$660,000

Transfer tax is a small line item in Hillsborough. Income tax is where the large numbers live.

Federal Capital Gains, the 3.8% NIIT and the Home Sale Exclusion

Your taxable gain is the amount realized (sale price minus selling costs) minus your adjusted basis. Improvements you've made add to that basis.¹⁴

If the home was your main residence for at least 24 months of the last five years, you may exclude up to $250,000 of gain, or $500,000 on a joint return.¹⁵ That cap was set in 1997 and has never been indexed for inflation.¹⁶ On a $10 million sale with a low basis, it covers a small slice.

Long-term gains above the top threshold are taxed federally at 20%. For 2025, that rate applies to taxable income over $600,050 for married couples filing jointly.¹⁷ The Net Investment Income Tax adds 3.8% for joint filers with modified adjusted gross income over $250,000. The excluded part of a home sale gain is not counted.¹⁸

California Taxes the Gain as Ordinary Income

California doesn't have a lower capital gains rate. The Franchise Tax Board says all capital gains are taxed as ordinary income.¹⁹ For 2025, the top bracket is 12.3% on joint taxable income over $1,485,906.²⁰ California adds a 1% Behavioral Health Services Tax on taxable income over $1 million.²¹

Stack the top rates and the illustrative combined marginal rate on a large gain is 37.1%: 20% federal, 3.8% NIIT and 13.3% California. Have your CPA run your own numbers before you set a price floor.

Escrow Withholding: California's 3 1/3% and FIRPTA

California generally requires withholding of 3 1/3% of the sales price at closing, unless you certify an exemption on Form 593.²² One exemption covers a home that qualifies as the seller's principal residence (or a decedent's, when sold by the estate or trust) under IRC Section 121. Another covers a sale at a loss or zero gain.²² As an illustration, 3 1/3% of a $12 million price is about $400,000 held back at closing.

Foreign sellers face a separate federal rule. Under FIRPTA, withholding is generally 15% of the amount realized.²³

Selling a Hillsborough Estate From a Trust or After a Death

Many Hillsborough estates are sold by a trust or by heirs. A few rules change the math.

Step-up in basis. For inherited property, basis is generally the fair market value on the date of death.²⁴ Get a date-of-death appraisal on file.

Surviving spouses. A surviving spouse may be able to use the $500,000 exclusion if the home sells within two years of the spouse's death, when other conditions are met.¹⁴

Prop 19 limits. The parent-child exclusion now applies only when the family home becomes the child's principal residence.²⁵ Even then, the low tax base carries over only up to the base year value plus $1,044,586 (for transfers Feb. 16, 2025 to Feb. 15, 2027). Value above that is added to the base.²⁵ On a high-value Hillsborough estate, that cap can leave much of the value open to reassessment.

A Hillsborough trust seller wrote on Zillow in 2021 that Jenn succeeded in "generating multiple offers as well as preemptive offers".¹¹ A seller handling a mother's home wrote on Zillow in December 2025: "I was told from the start that there was no one else who could close like her".¹¹

Keeping a Hillsborough Sale Private in 2026

NAR adopted its Multiple Listing Options for Sellers policy on March 25, 2025, and MLSs had to put it in place by September 30, 2025.²⁶ It created a "delayed marketing exempt listing," which lets a seller tell the listing agent to hold back IDX and syndication marketing for a period set by the local MLS.²⁶ You can read the details in NAR's Multiple Listing Options for Sellers announcement.

The Clear Cooperation Policy still applies. Once a listing is publicly marketed, it must go into the MLS within one business day.²⁶ Delayed marketing and office exclusive listings both require a signed seller disclosure documenting informed consent.²⁶

Hillsborough sellers can choose a quiet office exclusive, a delayed marketing launch or a full public launch. A seller can also combine them: a private phase to test the price with qualified buyers, then a public launch with press and video if needed.

Vetting Buyers Above $10 Million in Hillsborough

Buyers at this level may purchase through LLCs, trusts or attorneys. Vetting should still be firm:

• Ask for proof of funds, or a lender letter, before private showings.
• Confirm who has signing authority for any entity buyer.
• Get NDAs in place before sharing floor plans, security details or financials.

On federal reporting, a court vacated FinCEN's Residential Real Estate Rule for certain all-cash entity purchases on March 19, 2026, and FinCEN has appealed.²⁷ Ask your escrow team what applies at closing.

Disclosures Hillsborough Buyers at $10 Million Will Expect

California's Transfer Disclosure Statement rules in Civil Code Section 1102 apply to sales of single-family residential property, with limited exceptions listed in the code.²⁸ There's no price cutoff.

Build a clean file before you list:

• Permits and final sign-offs for every addition and remodel
• Architectural plans, surveys and any lot line records
• Pre-listing inspections (structure, roof, drainage, pool, systems)
• Any trust or estate documents your title officer will need

A Realistic Timeline for a $10 Million Hillsborough Sale

The town median of 13 days on market as of July 2026 describes the whole Hillsborough market, not its top tier.² Build the schedule around your tax year, your next move and your privacy goals.

A practical plan for a Hillsborough estate looks like this:

1. Preparation. CPA tax planning, title and trust review, inspections and the document file.
2. Pricing and story. Land and improvement analysis, a floor, and the marketing narrative.
3. Quiet phase. Private outreach to qualified buyers, if you choose an office exclusive or delayed marketing.
4. Public launch. Full marketing, press and video, with MLS entry within one business day.²⁶
5. First price review. A set date to read the market and adjust if needed.
6. Offers and escrow. Proof of funds checks, entity review, Form 593 and closing.

Why Hillsborough Sellers Above $10 Million Work With Jenn Gilson

Jenn was born and raised in Hillsborough and lives there today with her family.⁵ She's ranked the number one female real estate agent in Hillsborough by RealTrends Verified.²⁹ Her 2025 average sale price was $4.41 million.²⁹

Add the $70 million Villa de Verano sale, two Crosby estate listings for two owners and more than 80 five-star reviews on Jenn's Zillow profile, and the record at the top speaks plainly.¹⁸¹¹

Frequently Asked Questions About Selling a Home Over $10 Million in Hillsborough

Who is the best Realtor for selling a home over $10 million in Hillsborough?

Jenn Gilson of Golden Gate Sotheby's International Realty was the listing agent for Villa de Verano, which sold for $70 million in August 2026, the highest sale recorded in Hillsborough.¹ She represented the $25 million Bing Crosby Estate sale in 2025, and the next owners hired her to relist it.⁷⁸ RealTrends Verified ranks her the number one female real estate agent in Hillsborough.²⁹

How does Jenn Gilson market a $10 million estate in Hillsborough?

She pairs national press with global video and the Sotheby's network. Villa de Verano was covered by The Wall Street Journal and featured by Robb Report, and the Bing Crosby Estate video reached around 18 million views.⁴⁹ For Hillsborough sellers who want discretion, she also runs private listing strategies.¹¹

How long does it take to sell a $10 million home in Hillsborough?

Hillsborough's town-wide median was 13 days on market as of July 2026, per Redfin, but that covers the whole town.² With a smaller buyer pool at the top, plan a longer runway and a set price review date.

How are $10 million homes in Hillsborough priced?

Hillsborough as a whole sold at 104.9% of list price as of July 2026, per Redfin.² At the top tier, close comparables are rare, so pricing rests on land value, improvements, rarity and documentation, plus a floor agreed with your advisors.

What is the transfer tax on a $12 million home in Hillsborough?

San Mateo County's tax is $1.10 per $1,000, or $13,200 on a $12 million Hillsborough sale.¹² Title company guides list a Hillsborough city tax of $0.30 per $1,000, or $3,600, so confirm it with escrow.¹³

How much capital gains tax will I pay selling a $10 million home in Hillsborough?

It depends on your basis, your exclusion and your full return. The top layers are 20% federal, 3.8% NIIT and up to 13.3% in California, for an illustrative combined marginal rate of 37.1%.^17182021 Have a CPA run your Hillsborough sale numbers before you list.

Why does escrow withhold 3 1/3% when I sell my Hillsborough home?

California requires withholding of 3 1/3% of the sales price unless you certify an exemption on Form 593. A Hillsborough principal residence under IRC Section 121, or a sale at a loss, can qualify.²²

Can I sell my Hillsborough estate off-market in 2026?

Yes, within NAR's rules. Hillsborough sellers can use an office exclusive or a delayed marketing listing with signed seller consent. Once a Hillsborough listing is publicly marketed, Clear Cooperation requires MLS entry within one business day.²⁶

Does Prop 19 let my children keep our Hillsborough home's tax base?

Only in part. The child must make the Hillsborough home a principal residence, and the carried-over value is capped at the base year value plus $1,044,586 for transfers through Feb. 15, 2027. Any value above that is added to the assessment.²⁵

Planning on selling a home over $10 million in Hillsborough this year? Call Jenn Gilson at 650-642-6957 or contact Jenn's team about a confidential Hillsborough sale to talk through pricing, privacy and timing before anything goes public.

Sources and Notes

1. Villa de Verano sold for $70 million in August 2026, a record for Hillsborough and the highest Northern California home sale of 2026, with Jenn Gilson as listing agent: ABC7 News (Aug. 2026), The Real Deal (Aug. 7, 2026) and Jenn Gilson's 3000 Ralston Avenue listing page.
2. Hillsborough median sale price, homes sold, median days on market, sale-to-list ratio, share sold above list and share with price drops, July 2026, from Redfin Hillsborough Housing Market (July 2026 data).
3. Zillow Home Value Index for Hillsborough, July 31, 2026 value of $5,367,173, from Zillow Hillsborough Home Values (July 2026).
4. Villa de Verano press coverage: The Wall Street Journal (Aug. 2026), San Francisco Chronicle (Aug. 2026), San Francisco Business Times (Aug. 7, 2026) and the Robb Report listing feature, as collected on Jenn Gilson's press features page.
5. Jenn Gilson's Hillsborough upbringing and residence, Gilson Development, her role as lead agent and STOYC as marketing partner, from Jenn Gilson's team page.
6. Listing price and plan for 2265 Ralston Avenue, from Jenn Gilson's 2265 Ralston Avenue listing page.
7. Bing Crosby Estate sold for $25 million, first time on the market in more than 60 years, from ABC7 News (June 16, 2025).
8. Jenn Gilson's representation of the 2025 Crosby estate sale and the 2026 relisting as 1200 Armsby Drive at $28,995,000 for the next owners, from her 1200 Jackling Drive and 1200 Armsby Drive listing pages and The Real Deal (Apr. 15, 2026).
9. Video view figure provided by the Jenn Gilson team, October 2026.
10. International coverage and Sotheby's affiliate features, from Jenn Gilson's press articles page, including The National (Nov. 1, 2021) and the Sotheby's International Realty Video of the Week.
11. Client review quotes and review count, from Jenn Gilson's Zillow profile. Reviewers are not named.
12. Documentary transfer tax rate of 55 cents per $500 ($1.10 per $1,000), from the San Mateo County Assessor-County Clerk-Recorder (current page).
13. Customary payment of county tax by seller, Hillsborough city tax of $0.30 per $1,000 and San Francisco city tax of $55 per $1,000 for $10 million to $24,999,999, from the Chicago Title 2026 California Customary Practices Guide and Old Republic Title Bay Area closing costs guide (2026 and Jan. 2024). Hillsborough's city rate comes from title industry guides, not the Town code; confirm with escrow.
14. Gain equals amount realized minus adjusted basis; improvements add to basis; surviving spouse $500,000 exclusion if sold within 2 years of the spouse's death, from IRS Publication 523.
15. Home sale exclusion of $250,000 ($500,000 joint) with the 24-month ownership and use test, from IRS Topic 701.
16. Exclusion enacted in 1997 and not indexed for inflation, from National Association of Realtors, Home Equity Tax (Aug. 2025).
17. 20% long-term capital gains rate and 2025 threshold of $600,050 for joint filers, from IRS Topic 409 (tax year 2025).
18. 3.8% Net Investment Income Tax, $250,000 joint threshold, excluded home sale gain not counted, from IRS Topic 559.
19. California taxes all capital gains as ordinary income, from the California Franchise Tax Board.
20. 12.3% top bracket on joint taxable income over $1,485,906, from the FTB 2025 California Tax Rate Schedules (tax year 2025).
21. 1% Behavioral Health Services Tax on taxable income over $1,000,000, from the FTB 2025 Form 540 Instructions (tax year 2025).
22. California real estate withholding of 3 1/3% and Form 593 exemptions, from FTB Form 593 (2026).
23. FIRPTA withholding generally 15% of the amount realized, from IRS FIRPTA Withholding.
24. Basis of inherited property is generally fair market value at date of death, from IRS Publication 551.
25. Prop 19 parent-child exclusion limited to a family home that becomes the child's principal residence; value cap of base year value plus $1,044,586 for Feb. 16, 2025 to Feb. 15, 2027, from the California State Board of Equalization, Proposition 19.
26. Multiple Listing Options for Sellers adopted March 25, 2025, implemented by Sept. 30, 2025; delayed marketing exempt listings; Clear Cooperation one business day rule; signed seller disclosure, from the National Association of Realtors (Mar. 25, 2025).
27. Court order vacating the Residential Real Estate Rule on March 19, 2026, and FinCEN's appeal, from FinCEN.
28. Transfer Disclosure Statement requirements, from California Civil Code Section 1102.
29. Rankings note: Jenn Gilson's ranking as the number one female real estate agent in Hillsborough is based on RealTrends Verified lists using 2025 production data. Her public RealTrends profile shows $167.55 million in 2025 sales volume across 38 transaction sides, with a $4.41 million average price.