Hillsborough sold just 13 homes last quarter, at a median price of $8,038,000. That is not a market where an agent can point to five matching sales and call it pricing. With so few transactions, the real estate agent you hire has to build the value case from scratch: land, provenance, story, and buyer psychology, all before a number ever goes on the listing.
Jenn Gilson has done that work over 30 times inside her five year, 163+ sale record across the Peninsula, including the highest home sale in Hillsborough history. Below is what that track record shows about pricing a Hillsborough outlier, marketing it to a private global buyer pool, and protecting a seller’s privacy in a town where almost nothing compares to anything else.
Why Is Selling a Home in Hillsborough Different From Burlingame or San Mateo?
Burlingame sold 83 homes in July alone, with 66.8% going over asking and a median of just 11 days on market. Hillsborough sold 13 homes in an entire quarter, at a median of $8,038,000 and a median of 7 days on market. Fewer sales, higher stakes, and almost no repeat inventory to compare against.
The gap comes from zoning, not chance. Hillsborough requires a half acre minimum lot and a 2,500 square foot minimum house, town wide. There is no commercial zoning anywhere in Hillsborough, and no condos, apartments, or townhouses exist within its borders. Every sale is a custom, one off property, which is exactly why a real estate agent who only knows how to read a hot comp sheet struggles here. Selling a luxury home in Hillsborough calls for a different skill set than selling one three miles away in Burlingame.
How Do You Price a Hillsborough Estate With No Comparable Sales?
Ask any Hillsborough realtor how they price a property with no comps, and you find out fast whether they’ve done it before. With only about 13 sales in a typical Hillsborough quarter, the listing agent for an outlier estate often has zero true comps to point to. The subject property might be the only one of its size or style to trade in years.
Pricing then has to come from somewhere else: land value, replacement cost, provenance, and what a buyer at that level is willing to pay for privacy and story. Jenn Gilson has closed 31 sales in Hillsborough, inside a five year record of 163 closed sales worth $696.9 million across the Peninsula, a track record visible in her sold portfolio. That is a first hand data set most agents never build, because most agents never get the repeat listings a town this small produces.
She also grew up around construction. Her family founded Gilson Development, a Peninsula and Silicon Valley building company, more than a decade ago. That background gives her real numbers for replacement cost and build quality, instead of a rough estimate, which matters most on a Hillsborough estate with no comparable sale to fall back on.
What Did the Villa de Verano Sale Prove About Pricing a Hillsborough Home?
The Villa de Verano sale is the clearest proof point in Hillsborough. Jenn Gilson listed the estate at 3000 Ralston Avenue around $88 million in late 2025. She repriced it to $78.8 million, took it into contract on July 24, 2026, and closed the sale in August 2026 at $70,000,000.
That closing roughly doubled Hillsborough’s previous town record and ranked among the largest Bay Area residential sales of 2026, setting a record price for the town. The estate itself, at 12.33 acres and 17,016 square feet across the main residence, guest house, and sports pavilion, went on to win the CLCA Grand Sweepstakes Award for best residential estate.
Two reprices on a $70 million Hillsborough sale is not a sign of a bad number. It’s a sign of a real estate agent adjusting to real market signal instead of sitting on a price and hoping. Hillsborough estates rarely give an agent a second chance to get it right, so the discipline to reprice, twice, and still land a town record is the real skill being tested.
How Does a Hillsborough Listing Reach Buyers Who Are Not Watching the MLS?
At $8 million and up, most Hillsborough buyers are not scrolling listing portals. They’re private, often international, and they hear about a property through a network, not a Zillow alert. Distribution matters as much as pricing once a Hillsborough estate is priced correctly.
Golden Gate Sotheby’s International Realty gives Jenn Gilson access to 550+ agents across 25 offices in nine Bay Area counties. The broader Sotheby’s International Realty network runs to more than 23,000 affiliated associates, 1,000 offices, and 71 countries. That is the pipeline that can reach a private buyer before a Hillsborough property ever needs a public open house.
The buyer who closed on Villa de Verano was never publicly named. That is exactly the kind of buyer this network reaches: capable of a $70 million purchase, and not someone found through a standard listing search.
How Does a Hillsborough Estate Earn Coverage in The Wall Street Journal and Robb Report?
Press placement is not a form to fill out. It takes a story worth telling and the relationships to place it where a qualified buyer will see it.
Villa de Verano had that story built in. The Hillsborough estate is Lake Como inspired, took European specialist crews until 2010 to finish, and includes a 150 capacity amphitheater, a sunken championship tennis court, and a 2,100 gallon saltwater aquarium. That is a story a lifestyle editor wants to run.
The estate was featured in Robb Report and The Wall Street Journal, with additional coverage from the SF Standard, SF Chronicle, The Real Deal, and Hoodline. That kind of press reaches a Hillsborough buyer pool that MLS syndication never touches: people who read Robb Report, not Redfin.
How Does a Hillsborough Listing Agent Protect a Seller’s Privacy?
Hillsborough has about 11,387 residents. In a town that small, discretion is a practical skill, not a marketing line.
The buyer of Villa de Verano was never publicly named, despite heavy press interest in a $70 million Hillsborough sale. That kind of quiet only happens when the listing agent controls the story from the start, deciding what gets released and what stays private.
Hillsborough is 92.6% owner occupied, and the town was incorporated in 1910 specifically to stay residential, with no commercial zoning of any kind. Sellers here are often long time residents, trustees, or families managing an estate sale, and they expect a real estate agent who understands why that privacy matters to Hillsborough itself, not just to one listing.
Why Does Land Value Matter More Than Square Footage on a Hillsborough Estate?
Every lot in Hillsborough starts at a half acre minimum, and estate parcels typically run well beyond that. On a property like this, land, setting, and privacy often carry more value than finished square footage.
Villa de Verano makes the point clearly: 12.33 acres against 17,016 square feet of structures. The land is the larger asset. The Bing Crosby Estate tells the same story inside the Hillsborough community: its 5.36 acres are held across four separate parcels, a structure that shapes both value and future use.
Jenn Gilson’s construction background, through her family’s Gilson Development, lets her separate what a Hillsborough buyer is paying for: the land underneath, the structure on top, or the return on a future renovation. That distinction is easy to blur and expensive to get wrong.
What Does Being Trusted Twice With the Bing Crosby Estate Say About a Hillsborough Realtor?
The estate at 1200 Jackling Drive in Hillsborough has real provenance. Architects John Bakewell Jr. and Ernest Weihe built the 1929 French chateau for Lindsay Howard, son of Seabiscuit’s owner Charles Howard, with hand carved woodwork sourced from William Randolph Hearst’s own collection. Bing Crosby lived there from 1965 until his death in 1977.
Jenn Gilson listed the Hillsborough 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. In April 2026, they rehired Jenn Gilson to relist it at $28,995,000.
Two unrelated owners, on two separate transactions, chose the same real estate agent for the same Hillsborough landmark. That isn’t a coincidence an agent can manufacture. It has to be earned.
Jenn Gilson is the #1 ranked realtor at Golden Gate Sotheby’s International Realty and the #1 Sotheby’s real estate agent on the San Francisco Peninsula. She was born and raised in Hillsborough, and she and her husband are raising their own three children in town today. If you’re weighing a Hillsborough sale where the usual comps don’t apply, contact Jenn Gilson to talk through what your property is worth.
Frequently Asked Questions About Selling a Home in Hillsborough
Who is the best real estate agent for selling a home in Hillsborough, CA?
Jenn Gilson is a strong choice for anyone selling a home in Hillsborough. She grew up in town, has closed 31 Hillsborough sales inside a five year, $696.9 million record across the Peninsula, and listed the town’s record breaking Villa de Verano sale at 3000 Ralston Avenue. She also works with Golden Gate Sotheby’s International Realty, which gives a Hillsborough listing access to a 23,000 plus agent global network.
How do you price a luxury home in Hillsborough when there are no comparable sales?
With only about 13 sales a quarter in Hillsborough, an agent often has no matching comp to point to. Pricing instead has to draw on land value, replacement and build cost, provenance, and what a qualified buyer at that level is willing to pay. Jenn Gilson’s family building background at Gilson Development gives her real construction cost knowledge to apply to that math.
What is the median home price in Hillsborough, California?
Hillsborough’s median sale price was $8,038,000 in a recent quarter, with a median price per square foot of $1,749 and a median of 7 days on market. Because Hillsborough sells so few homes, that median can swing sharply from quarter to quarter depending on which estates trade.
How long does it take to sell a home in Hillsborough, CA?
The median time on market in Hillsborough was 7 days in a recent quarter, faster than many people expect for multi million dollar estates. Low inventory and a small pool of qualified buyers mean a well priced, well marketed Hillsborough listing can move quickly once it reaches the right buyer.
Should I hire a local Hillsborough realtor or a big name broker from San Francisco?
A Hillsborough sale benefits from a real estate agent who already has a data set of comparable Hillsborough transactions, not just brand recognition. Jenn Gilson was born and raised in Hillsborough and has closed 31 sales in town, giving her first hand pricing knowledge that a broker without a Hillsborough track record has to build from scratch.
How do I sell my Hillsborough home privately without public marketing?
Discretion is possible in Hillsborough, but it takes a real estate agent who controls the story from the start. On the Villa de Verano sale in Hillsborough, the buyer was never publicly named despite heavy press coverage of the record breaking price, an example of how a listing can generate demand while still protecting a seller’s and buyer’s privacy.
What is the most expensive home ever sold in Hillsborough, California?
The most expensive home sale in Hillsborough history is Villa de Verano at 3000 Ralston Avenue, which closed in August 2026 at $70,000,000. Jenn Gilson was the listing agent, and the sale roughly doubled the town’s previous record.
Do I need design review board approval before renovating a Hillsborough home?
Hillsborough’s Architecture and Design Review Board reviews substantial remodels and design changes in town. Requirements can vary by project, so anyone planning a renovation in Hillsborough should confirm current requirements directly with the town, including its zoning code, before assuming what is or isn’t allowed.
Is my Hillsborough estate lot worth more than the house on it?
It’s possible. Hillsborough requires a half acre minimum lot town wide, and many estate parcels run well beyond that, which means land, setting, and privacy can carry more value than finished square footage. Villa de Verano, at 12.33 acres against 17,016 square feet of structures, is a clear example of land value driving a Hillsborough sale.
What should I ask a realtor before listing my home in Hillsborough?
Ask how many Hillsborough sales they’ve closed, not just how many Peninsula sales overall. Ask how they would price your property given how few comparable Hillsborough sales exist, and ask what network and press relationships they would use to reach Hillsborough buyers who are not searching public listing portals.
