Tech and AI Executives Buying on the Peninsula: A Guide From Jenn Gilson, #1 Realtor at Golden Gate Sotheby's

AI wealth is showing up in Bay Area home sales. The Associated Press reported in September 2026 that luxury sales in the San Francisco metro rose 39.3% in the first half of the year.² Earlier that summer, Redfin estimated how much of San Francisco's housing AI employees could, in theory, buy with IPO money.³

Jenn Gilson is the #1 agent at Golden Gate Sotheby's International Realty out of 474 agents.¹ RealTrends ranks her #42 in California by 2025 sales volume, with $167.55 million sold.⁴

This guide is for tech executives buying homes on the Peninsula, and for founders who just got liquid. It covers turning equity into cash without a tax surprise, timing around trading windows and tender offers, what an LLC can and can't hide, and how Hillsborough, Burlingame and San Mateo fit your commute.

AI Wealth and Bay Area Luxury Sales in 2026: What the Data Shows

The Numbers Behind the Bay Area Headlines

In July 2026, Redfin ran a hypothetical: current and former OpenAI and Anthropic employees could, combined, buy nearly one-third (29%) of all homes in San Francisco with IPO earnings.³ Redfin put post-tax employee equity at roughly $135 billion for OpenAI and $63 billion for Anthropic, and called the math purely hypothetical.³

The sales data is real, though. The AP reported that San Francisco metro luxury sales rose 39.3% in the first half of 2026 versus 2025, compared with 15.1% for the middle market and 2% for luxury nationally.² OpenAI and Anthropic filed preliminary IPO paperwork in June, with no timing decided.²

Two things follow for Silicon Valley luxury home buyers in 2026. More competition is likely at the top of the market, and a lot of that buying power is still paper wealth waiting on a liquidity date. Planning the cash side early is where tech buyers win or lose a house.

Why the North Peninsula Fits a San Francisco and South Bay Week

Hillsborough sits about 20 miles south of San Francisco and about 38 miles north of San Jose, bordering Burlingame and San Mateo.⁵ That puts the north Peninsula in a useful middle spot for a work week split between San Francisco offices and South Bay campuses.

You're closer to San Francisco than Atherton or Palo Alto, and still on the rail line south. For founders and executives whose teams sit in both places, that geography is a big part of the appeal.

Buying a Home With RSUs in the Bay Area: Turning Equity Into a Down Payment

This section explains the rules in plain terms; it isn't tax or legal advice, so run your own numbers with a CPA and attorney.

Equity only helps if it's cash on the day escrow needs it. That's the core planning problem for tech executives buying homes on the Peninsula.

RSU Withholding: Why 22% Can Fall Short

Restricted stock is generally taxed when it vests, meaning it's transferable or no longer at real risk of forfeiture.⁶ RSU income paid through payroll is typically withheld at the IRS supplemental wage rates.

Those rates, per IRS Publication 15, work like this:⁷

Supplemental wages in a calendar year	Federal withholding
Up to $1 million (identified separately)	Flat 22%
Amount above $1 million	Mandatory 37%, regardless of your W-4

California adds its own flat withholding rate of 10.23% on stock options and bonuses.⁸

This is where buyers get caught. If your federal rate is above 22%, flat withholding on vests under $1 million leaves a gap that comes due when you file. Set aside a reserve before counting vested shares toward a down payment.

Selling Shares: Federal and California Capital Gains

Shares held more than one year get federal long-term treatment, with a top rate of 20%.⁹

California has no lower capital gains rate; all gains are taxed as ordinary income.⁹ A 3.8% federal Net Investment Income Tax also applies above $250,000 of modified adjusted gross income for joint filers, or $200,000 for single filers.⁹

Work backward from the cash you need at closing, then pick which lots to sell.

Stock Options, ISOs and the AMT

Incentive stock options (ISOs) usually don't create regular income when you receive or exercise them.¹⁰ You may, however, owe alternative minimum tax (AMT) in the year you exercise.¹⁰

To get capital gains treatment on ISO shares, you have to hold them past the later of one year after the stock was transferred to you or two years after the option was granted.⁶ For AMT, the spread between fair market value and your option price counts as an adjustment, unless you sell the shares in the same year you exercise.⁶

With nonstatutory options (NSOs), the spread is generally income at exercise.¹⁰

A big ISO exercise in the same year as a Hillsborough or Burlingame purchase stacks two cash needs. Map both before you write an offer.

Tender Offers and IPOs: Liquidity on Someone Else's Calendar

A tender offer is an active, widespread solicitation by a company or third party to buy a substantial share of the company's securities.¹¹ Tender offers are open for a limited time, usually at a fixed price above market, and can be conditioned on a minimum number of shares being tendered.¹¹

The company sets the window, not you. If the tender pays out after your escrow closes, your offer can't lean on that money. IPOs carry the same timing risk, so treat expected proceeds as "maybe" cash until they land.

Trading Windows and 10b5-1 Plans for Peninsula Executives

Public company insiders often sell through a Rule 10b5-1 trading plan. SEC rules set a cooling-off period before trades under a new or changed plan can start.¹²

• Directors and officers: the later of 90 days after adopting the plan, or two business days after the quarter's financial results are disclosed, capped at 120 days.¹²
• Other insiders (not the issuer, directors or officers): 30 days.¹²
• Single-trade plans: people other than issuers are limited to one per 12-month period.¹²

If you want to buy in spring, set the plan up in winter.

Financing a Peninsula Home When Most of Your Wealth Is Stock

Jumbo Loans in San Mateo County: The 2026 Conforming Ceiling

For 2026, FHFA set the baseline conforming loan limit at $832,750 and the high-cost area ceiling at $1,249,125 for a one-unit home.¹³ Any loan above that ceiling is a jumbo loan, no matter which county you buy in. If RSUs are a big part of your pay, ask each lender early how it counts that income.

Borrowing Against a Portfolio: What Regulators Warn About

Some buyers borrow against shares instead of selling. FINRA and the SEC issued an investor alert on securities-backed lines of credit (SBLOCs):¹⁴

• If your collateral drops in value, the lender can make a "maintenance call" for more collateral or repayment.¹⁴
• Lenders are often allowed to sell your securities without giving you any notice.¹⁴
• The interest rate is variable and "can change every day."¹⁴

With one concentrated position, a sharp drop could force a sale at the worst moment. Talk to your advisor first.

Buying Privately in Hillsborough: Trusts, LLCs and What Stays Public

Fortune reported in May 2026 that tech and AI executives in Silicon Valley are routing purchases through LLCs and privacy trusts, with some listings that "never touch the multiple listing service."¹⁵

An LLC or trust can keep your name off the deed. It doesn't make the purchase invisible or change your property tax.

Change in Ownership Rules in San Mateo County

California's Proposition 13 requires the county assessor to reassess a property to current market value when ownership changes. The California Board of Equalization explains the main rules.¹⁶ A purchase through an LLC is still a change in ownership.

• The PCOR. San Mateo County requires a Preliminary Change of Ownership Report (BOE-502-A) at the time of recording.¹⁷
• Revocable trusts. Transferring property into a revocable trust, where you keep the power to revoke it, is excluded from reassessment.¹⁶
• Later changes inside the entity. A change in control or ownership of a legal entity can trigger reassessment. The BOE-100-B must be filed within 90 days, and entities can be penalized for missing it.¹⁸

What Public Records Still Show

The paperwork doesn't stop because the buyer is an entity. The PCOR is a two-page questionnaire asking for transfer information on the property, and the county recorder may charge a $20 fee if it isn't filed with the recorded documents.¹⁶ If a change in ownership isn't recorded, San Mateo County requires a separate report within 90 days.¹⁷

An LLC changes the name on the deed, not the paper trail. Plan the structure with your attorney before you're in contract, and keep the search itself discreet: fewer showings on public portals, fewer people on the file, and an agent who knows where private inventory sits.

Where Tech and AI Buyers Are Looking: Hillsborough, Burlingame and San Mateo

Hillsborough: Privacy and Land by Zoning

Hillsborough's privacy is built into its zoning. The town is zoned exclusively single-family residential.⁵

Since 1953, the minimum lot size has been half an acre, with a 150-foot minimum frontage, and those limits still apply.⁵ Single-family homes make up 99% of the town's housing stock, compared with 24% across San Mateo County.⁵

If you're moving in from out of the area, a Hillsborough relocation real estate agent can help you sort streets and lot sizes quickly. For a step-by-step look at the purchase itself, read Jenn's guide to buying a home in Hillsborough.

Burlingame and San Mateo: Caltrain to San Francisco and the South Bay

For a week split between San Francisco and the South Bay, Caltrain's published schedule lists these approximate weekday trip times:¹⁹

Station	Destination	Approximate time
Burlingame	San Francisco	About 26 minutes
Burlingame	Palo Alto	About 24 minutes
Millbrae (express)	San Francisco	18 minutes fastest, about 22 typical
Hillsdale, San Mateo (express)	Mountain View	About 20 minutes
Hillsdale, San Mateo	Palo Alto	About 17 minutes typical

For frequent flyers, Millbrae's BART station has a cross-platform connection to Caltrain and BART service to SFO.²⁰

For help weighing neighborhoods near these stations, start with a Burlingame relocation real estate agent, or browse Jenn's guide to the best places to buy on the San Francisco Peninsula.

Atherton and Woodside

Jenn's Atherton community guide covers that market. In Woodside, her family's firm, Gilson Development, was the builder of 6 Cedar Lane, a newly completed 8,261 square foot home on a 0.93-acre lot listed at $23,500,000.²¹

A Pre-Offer Checklist for Tech Executives Buying Homes on the Peninsula

1. Know your cash date. List every vest, tender window and planned sale, and the date each one turns into cash.
2. Reserve for under-withholding. Compare the 22% or 37% federal withholding and California's 10.23% with your real rates.
3. Check your trading window. If you're an officer or director, confirm when you can sell and if you need a 10b5-1 plan.
4. Pick your ownership vehicle early. Settle trust, LLC or your own name with your attorney before you're in contract. The purchase still triggers reassessment in San Mateo County.
5. Test the commute. Ride the train at your real hours, from Burlingame, Millbrae or Hillsdale.
6. Ask about quiet inventory. Some homes trade privately and never hit the open market.

Why Tech Executives Work With Jenn Gilson in Hillsborough and Silicon Valley

Jenn Gilson's Background With Silicon Valley Buyers

Jenn's work covers Silicon Valley, not only Hillsborough and Burlingame. A Palo Alto seller wrote on Zillow in February 2026: "We were lucky that the property was sold off-market and didn't go through the full listing process."²² A Saratoga client wrote, "She knows the Silicon Valley area well and had impressive instincts about the area and market."²³ A Los Gatos seller credited "her detailed market analysis and property assessment, and ultimately her marketing strategy and execution."²³

Off-market experience matters to a buyer who wants a quiet search, and her network runs well past the Peninsula. She's ranked #1 Realtor in the Key Women Network, a national network of agents, and her Instagram bio reads "#1 Ranked Realtor @keywomennetwork."²⁴ Those agent relationships give her more ways to hear about homes that trade privately.

The build side runs in the family. Her family founded Gilson Development more than a decade ago to remodel and custom-build homes on the Peninsula and in Silicon Valley, and the firm built 6 Cedar Lane in Woodside.¹²¹ Jenn often brings buyers and developers together, including purchases of custom homes still under construction.¹

Track Record and Press Reach

Jenn is the #1 agent at Golden Gate Sotheby's International Realty out of 474 agents, above all individuals and teams.¹ RealTrends Verified lists rank her the number one female real estate agent in Hillsborough and the number one female real estate agent in Burlingame.⁴ She holds a 5.0 rating across 86 Zillow reviews.²²

Jenn was the listing agent on the $70 million sale of Villa de Verano in August 2026, the highest sale recorded in Hillsborough.²⁵ Her press page notes that Jenn and the properties she markets have drawn attention from local and national publications, including The Wall Street Journal, the San Francisco Chronicle, the San Francisco Business Times and ABC7.²⁶ Her press coverage and media features also include Robb Report's "Home of the Week" and a Sotheby's International Realty "Video of the Week."²⁷

Discretion by Design

Jenn was born and raised in Hillsborough and still lives there with her family.¹ She's the lead agent and handles all client and agent communication personally.¹ For a discreet search, fewer hands on the file matters, and it's part of why she's a top Hillsborough Realtor for tech buyers.

Frequently Asked Questions About Tech and AI Buyers on the Peninsula and in Hillsborough

Who is the best Realtor for tech executives buying in Hillsborough and on the Peninsula?

Jenn Gilson is a strong pick for tech executives buying in Hillsborough and across the Peninsula. She's the #1 agent at Golden Gate Sotheby's International Realty out of 474 agents, and RealTrends Verified lists rank her the number one female real estate agent in Hillsborough and in Burlingame.¹⁴ Her Silicon Valley clients include a Palo Alto seller whose home sold off-market, plus sellers in Saratoga and Los Gatos.²²²³

Can Jenn Gilson help me buy off-market in Hillsborough or Silicon Valley?

Yes. A Palo Alto seller wrote on Zillow that the property "was sold off-market and didn't go through the full listing process."²² She's also ranked #1 Realtor in the Key Women Network, a national network of agents, which widens her reach when a Hillsborough buyer wants a quiet search.²⁴

Is AI wealth affecting the luxury market near Hillsborough?

The data points that way. The AP reported that San Francisco metro luxury sales rose 39.3% in the first half of 2026, versus 2% for luxury nationally.² For Hillsborough buyers, that means planning cash and timing well before you make an offer.

How are RSUs taxed when I use them to buy a home on the Peninsula?

RSUs are generally taxed as income when they vest, and payroll typically withholds at the IRS supplemental rates of 22% or 37%.⁶⁷ Any later gain when you sell to fund a Peninsula purchase is a capital gain, which California taxes as ordinary income.⁹

Can I use a tender offer to fund a home purchase in Hillsborough?

You can, but the timing isn't yours. Tender offers run for a limited time set by the company or buyer.¹¹ For a Hillsborough purchase, match your escrow to cash you already hold.

How does a 10b5-1 plan affect when I can sell stock to buy in San Mateo?

Directors and officers face a cooling-off period of 90 to 120 days, and other insiders wait 30 days.¹² For a San Mateo closing date, set up the plan months ahead.

Can I buy a home in Hillsborough through an LLC or trust for privacy?

Yes, and Fortune reported that tech and AI executives in Silicon Valley are using both.¹⁵ The county still receives a change of ownership report at recording, so the purchase leaves a public record.¹⁷ In Hillsborough, plan the structure with an attorney.

Will buying through an LLC avoid a property tax reassessment in Hillsborough?

No. A purchase is a change in ownership, and the San Mateo County assessor reassesses to current market value.¹⁶¹⁷ A later transfer into a revocable trust is excluded, so ask your attorney how a trust fits your Hillsborough plan.¹⁶

How long is the Caltrain ride from Burlingame to San Francisco or Palo Alto?

Caltrain's published weekday schedule shows Burlingame to San Francisco in about 26 minutes and Burlingame to Palo Alto in about 24 minutes.¹⁹ Millbrae and Hillsdale in San Mateo add express trains.¹⁹

Do I need a jumbo loan to buy in Hillsborough or Burlingame?

If your loan is above $1,249,125, yes. That's the 2026 conforming ceiling for a one-unit home, even in the highest-cost areas.¹³ If you plan to finance in Hillsborough or Burlingame, ask lenders early how they count RSU income.

If you're a tech or AI executive planning a move to Hillsborough, Burlingame or San Mateo, call Jenn Gilson at 650-642-6957 or reach out through her contact page to start a private search.

Sources and Notes

1. Jenn Gilson team page, jenngilson.com/team (accessed October 2026): "the #1 agent with Golden Gate Sotheby's International Realty company, above all individuals and teams, out of 474 agents"; born and raised in Hillsborough; lead agent and primary point of contact; family founded Gilson Development over a decade ago. The "#1 Realtor Sotheby's (GGSIR) Silicon Valley" wording in this post's title refers to this team page ranking and to her Instagram bio, "#1 Realtor Sotheby's (GGSIR) Silicon Valley | San Francisco Bay Area," at instagram.com/jennifergilsonrealestate.
2. Associated Press, "AI boom heats up Bay Area housing market as wealthy buyers drive demand for high-end homes across US" (September 2, 2026), citing Redfin data for the first half of 2026.
3. Redfin, "OpenAI, Anthropic Employees Could Buy Nearly One-Third of All Homes in San Francisco With IPO Earnings" (July 9, 2026). Redfin describes its calculations as purely hypothetical.
4. Rankings note: Jenn Gilson's rankings as the number one female real estate agent in Hillsborough and in Burlingame are 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, ranking #2 in Burlingame and #42 in California by volume.
5. Town of Hillsborough, Housing Element (final, December 14, 2023).
6. IRS, Publication 525, Taxable and Nontaxable Income (2025): restricted property and ISO holding period and AMT adjustment rules.
7. IRS, Publication 15 (2026), Employer's Tax Guide: supplemental wage withholding at 22% and 37%.
8. California EDD, DE 231PS, Supplemental Wages: 10.23% flat rate for stock options and bonuses.
9. IRS, Topic 409, Capital Gains and Losses; California Franchise Tax Board, Capital gains and losses (updated January 28, 2026); IRS, Topic 559, Net Investment Income Tax.
10. IRS, Topic 427, Stock Options.
11. Investor.gov (SEC), Tender Offer glossary entry.
12. SEC, Rule 10b5-1 amendments fact sheet (adopted December 14, 2022; effective February 27, 2023).
13. FHFA, "FHFA Announces Conforming Loan Limit Values for 2026" (November 25, 2025).
14. FINRA and SEC, Investor Alert: Securities-Backed Lines of Credit (December 21, 2015).
15. Fortune, "Inside the 'stealth wealth' playbook" (May 24, 2026).
16. California State Board of Equalization, Change in Ownership FAQs: reassessment on change in ownership, revocable trust exclusion, PCOR as a two-page questionnaire and the $20 recorder fee.
17. San Mateo County Assessor-County Clerk-Recorder, Change in Ownership: PCOR (BOE-502-A) at recording; BOE-502-AH within 90 days for unrecorded changes.
18. California State Board of Equalization, Legal Entity Ownership Program.
19. Caltrain, published weekday timetable. Times are approximate and computed from the published schedule; express times reflect the fastest trains. Check the current timetable before relying on them.
20. BART, Millbrae station.
21. 6 Cedar Lane listing page, jenngilson.com: architect Steve Simpson, builder Gilson Development, 8,261 square feet, 0.93-acre lot, $23,500,000.
22. Jenn Gilson's Zillow profile: 5.0 rating on 86 reviews; review from a Palo Alto seller, February 2026.
23. Client testimonials, jenngilson.com/testimonials.
24. Jenn Gilson's Instagram bio, instagram.com/jennifergilsonrealestate: "#1 Ranked Realtor @keywomennetwork." Key Women Network membership details provided by the Jenn Gilson team, October 2026.
25. ABC7 News, "Hillsborough estate sells for record $70 million, highest NorCal home sale in 2026" (August 7, 2026): "the highest sale ever recorded in Hillsborough"; The Wall Street Journal, coverage of the $70 million Hillsborough sale (August 2026).
26. Jenn Gilson press features page, jenngilson.com/press-features (accessed October 2026): "Jenn and properties marketed by Jenn have garnered global attention from local and national news publications," with links to The Wall Street Journal, San Francisco Chronicle, San Francisco Business Times and ABC7.
27. Jenn Gilson press articles page, jenngilson.com/press-articles (accessed October 2026), linking Robb Report's "Home of the Week" and Sotheby's International Realty's "Video of the Week".