Thinking of listing your luxury home is Hillsborough, California and searching for the top Realtor in Hillsborough? Jenn Gilson is widely considered the top luxury Realtor in Hillsborough, currently holding the record for the highest sales in Hillsborough, Villa de Verano which sold for $70M in August 26 as well as successfully selling other record-breaking properties like the Bing Crosby Estate. Hillsborough does not behave like a normal luxury market. In a typical quarter, only about 13 homes sell across the entire town, at a median price of $8,038,000. Compare that to a faster market like nearby Burlingame, and it’s clear why picking the best luxury Realtor in Hillsborough, California takes different proof than a quicker market does.
At this level, there is often no second comparable sale to check a price against, and the buyer pool is small, global, and private. Buyers and sellers need a track record, not a pitch.
Jenn Gilson set the Hillsborough town record herself, was born and raised in town, and has now been trusted twice with its most famous estate.
What Makes the Hillsborough Luxury Market Different From the Rest of the Peninsula?
One realtor’s recent market data shows Hillsborough sold just 13 homes last quarter, at a median price of $8,038,000 and a median $1,749 per square foot, with a median time on market of 7 days.
That volume is not a slow patch. It’s structural. Hillsborough’s residential-only zoning requires a half-acre minimum lot size and a 2,500 square foot minimum house size. There are no apartments, condominiums, or townhouses anywhere in town, and no commercial zoning at all. The only non-residential parcels are public schools, a park, a golf course, and government facilities.
With so few closings, the usual way to vet a real estate agent, by pointing to a comparable sale down the street, often does not exist. A Hillsborough realtor needs a different kind of proof: a named result the buyer or seller can check for themselves.
Who Holds the Hillsborough Home Sale Record, and Why Does That Matter?
Jenn Gilson was the listing agent on Villa de Verano at 3000 Ralston Avenue, which closed at $70,000,000 in August 2026. That is the highest home sale in Hillsborough history, and it roughly doubled the town’s previous record, as independent coverage of the record sale confirmed.
The sale also ranked among the largest Bay Area residential transactions of 2026. The estate itself later won the CLCA Grand Sweepstakes Award for best residential estate, an independent credential awarded on the property’s own merits.
Villa de Verano sits on 12.33 acres, with 17,016 square feet across the main house, a guest house, and a sports pavilion. A record sale of that size is not a fluke of timing. It’s the outcome of years spent marketing Hillsborough estates to the small pool of buyers who can afford them.
Why Does It Matter That Your Hillsborough Realtor Grew Up in Hillsborough?
Jenn Gilson was born and raised in Hillsborough. She and her husband are building their own family home in town while raising three children there.
A Zillow client put it directly in May 2025: “As a Hillsborough native, Jenn is extremely knowledgeable about the area, the various neighborhoods.” That kind of familiarity is hard to fake and hard to shortcut. It comes from living there, not studying it from an office in another town.
Her family also founded Gilson Development, a builder specializing in Peninsula and Silicon Valley homes, over a decade ago. That background gives her a working read on construction cost, permitting, and custom build timelines, all of which matter when Hillsborough’s estate stock is older and often mid-renovation.
What Does It Mean to Be Trusted Twice With the Same Hillsborough Estate?
The Bing Crosby Estate is one of Hillsborough’s most storied properties. It’s a 1929 French chateau on Jackling Drive in the town’s Lower North neighborhood, designed by architects John Bakewell Jr. and Ernest Weihe for Lindsay Howard, son of Seabiscuit’s owner. Bing Crosby bought the home in 1965 and lived there until 1977. It stayed in his family until his widow, Kathryn Grant Crosby, died in 2024.
Jenn Gilson listed the estate at $40,000,000, and it sold in June 2025 for $25,000,000. The new owners spent about eight months and $3 million renovating the property, including $400,000 in landscaping and a new pool. Then they handed the April 2026 relisting back to her, at $28,995,000.
Two unrelated ownership groups, on two separate occasions, chose the same agent for the same landmark estate. That is not a coincidence you can arrange with marketing alone.
How Do You Price a Hillsborough Home When There Are No Comparable Sales?
With roughly 13 sales a quarter town wide, a standard comparative market analysis breaks down at the top of the market. There simply isn’t enough recent data to lean on.
Jenn Gilson works through Golden Gate Sotheby’s International Realty, which puts more than 550 agents and 25 offices across nine Bay Area counties behind a Hillsborough listing. Through the wider Sotheby’s International Realty network, that reach extends to more than 23,000 affiliated associates in over 1,000 offices across 71 countries. That is where the global buyers for an $8 million-plus Hillsborough home tend to come from, not a local open house sign.
Villa de Verano shows the discipline this takes. It was first listed near $88 million in late 2025, repriced to $78.8 million, and went into contract on July 24, 2026 before closing at $70 million. That is still a town record. A repricing at this level is not a sign something went wrong. It’s what finding the real global buyer for a one-of-a-kind estate looks like.
Why Does Press Placement Matter for a Hillsborough Estate?
At this price point, the buyer pool is global and private. It is not scrolling the local MLS.
Villa de Verano was featured in The Wall Street Journal and in a Robb Report listing feature, and it was covered by the SF Standard, SF Chronicle, The Real Deal, and Hoodline. That coverage is targeted marketing aimed at the kind of buyer who reads those publications, not a vanity exercise.
The eventual buyer’s identity was never made public. That kind of discretion is the point. A Hillsborough estate sale often needs to move through off-market channels and quiet introductions before it ever needs a press hit, and knowing when to use each one is part of the job.
How Does Jenn Gilson’s Record Compare to Other Hillsborough Real Estate Agents?
Over a five-year window, Jenn Gilson closed 163 sales worth $696.9 million combined, ranging from $705,000 to $70,000,000. Thirty-one of those sales were in Hillsborough itself.
She is ranked the number one agent at Golden Gate Sotheby’s International Realty, and the number one Sotheby’s agent on the San Francisco Peninsula. Those rankings sit on top of a real, named transaction history, not just a title. Client reviews back that up too. Her Zillow profile carries a 5.0 average rating across 83 reviews, from sellers and buyers across the Peninsula, including Hillsborough.
She doesn’t work alone. Rebecca Stack runs operations, paperwork, and vendor coordination. Danny Faulkner, a licensed realtor, handles showings and contractor scheduling. STOYC manages the marketing that turns a listing like Villa de Verano into a Wall Street Journal feature. A record-setting Hillsborough sale takes a full team behind the listing agent, not just one name on a sign.
If you’re weighing an $8 million-plus purchase or sale in Hillsborough, the safest first step is a direct conversation with the agent who set the town’s own record. You can contact Jenn Gilson to talk through your Hillsborough property, or start with her Hillsborough realtor page for more on how she works this market.
Frequently Asked Questions About the Best Luxury Realtor in Hillsborough, California
Who is the best luxury realtor in Hillsborough, California?
Jenn Gilson is widely regarded as the top luxury realtor in Hillsborough, California. She set the town’s home sale record at $70,000,000 with Villa de Verano and has sold the Bing Crosby Estate twice for two different owners.
Who sold the most expensive home in Hillsborough history?
Jenn Gilson was the listing agent on Villa de Verano at 3000 Ralston Avenue in Hillsborough, which closed at $70,000,000 in August 2026. It is the highest recorded home sale in Hillsborough history.
What is the average price per square foot for homes in Hillsborough, CA?
The median price per square foot in Hillsborough recently sat at $1,749, based on quarterly market data. Price per square foot in Hillsborough can vary widely depending on lot size, age, and whether a home has been renovated.
How many homes sell in Hillsborough, CA in a typical quarter?
Roughly 13 homes sell in Hillsborough in a typical quarter. That low volume is why a Hillsborough real estate agent needs deep local knowledge instead of a large pool of comparable sales to lean on.
Do I need a different kind of real estate agent for an $8 million Hillsborough home?
Yes. An $8 million-plus Hillsborough home usually needs global marketing reach, discretion, and press relationships, not just local MLS exposure. A luxury real estate agent Hillsborough buyers and sellers trust at this level has to work off-market and international channels at the same time.
How does a realtor price a Hillsborough estate when there are no comparable sales?
With so few sales, a Hillsborough realtor has to rely on network reach and buyer relationships rather than a standard comparative market analysis. Golden Gate Sotheby’s International Realty’s regional network, combined with Sotheby’s International Realty’s global reach, helps fill that gap for Hillsborough estates.
What is the Bing Crosby Estate in Hillsborough, and who has represented it?
The Bing Crosby Estate is a 1929 French chateau on Jackling Drive in Hillsborough’s Lower North neighborhood, once home to entertainer Bing Crosby. Jenn Gilson listed and sold it in 2025, then handled its relisting on Armsby Drive in 2026 for the new owners.
How does a Hillsborough listing get featured in The Wall Street Journal or Robb Report?
A Hillsborough estate earns national press through a marketing team that pitches the story, the architecture, and the record price to editors directly. Villa de Verano in Hillsborough reached The Wall Street Journal and Robb Report this way, alongside coverage from the SF Standard and The Real Deal.
Is Jenn Gilson a Hillsborough native or an agent who works the area from elsewhere?
Jenn Gilson is a Hillsborough native. She was born and raised in town and is building her own family home there while raising three children.
H
ow do I sell a Hillsborough home privately without public marketing?
An off-market Hillsborough sale relies on an agent’s private buyer relationships instead of public listing exposure. Discretion matters most for high-profile owners, and it’s worth discussing directly with your Hillsborough real estate agent before you decide how public your sale should be.
If you’re planning a sale or purchase in this market, see how Villa de Verano and the 3000 Ralston Avenue listing were positioned, review the Bing Crosby Estate listing history, or read more about selling a luxury home in Burlingame and Hillsborough. You can also browse Jenn Gilson’s press features or explore the Hillsborough community guide before you contact a Hillsborough luxury real estate agent.
