Looking for the best relocation real estate specialist in Hillsborough? Speak with Jenn Gilson, top Hillsborough Realtor and relocation specialist. Hillsborough, California breaks the standard relocation playbook. There are no apartments, condominiums or townhouses anywhere in town, and there’s no commercial zoning at all. You can’t rent a place for a year while you learn the streets, because that rental stock doesn’t exist here. There’s no downtown to land in either. Half-acre minimum lots and a 2,500 square foot minimum house size keep it that way.
Jenn Gilson was born and raised in Hillsborough. She and her husband are building their own home here while raising three children, and she’s closed 31 Hillsborough sales, more than any city she serves besides Burlingame.
Why Is Relocating to Hillsborough Different From the Rest of the Peninsula?
Most Peninsula cities mix housing types: single-family homes, condos, apartments, a downtown strip. Hillsborough doesn’t. Zoning here allows single-family homes only, on a minimum half-acre lot with a minimum 2,500 square foot house. The town’s zoning ordinance sets those minimums town-wide.
There’s no commercial zoning anywhere in Hillsborough. The only non-residential parcels are four public schools, one park, a golf course and a few government facilities. No grocery store, no coffee shop, no strip mall to browse while you wait for the right house.
The numbers back this up. About 92.6% of homes here are owner-occupied. Population sits around 11,387 people spread across 6.17 square miles, 17 miles south of San Francisco, according to Wikipedia’s entry on Hillsborough. Jenn grew up in this town, and she and her husband are building their own home in Hillsborough right now while raising three kids. She’s making the same housing decisions her clients are making, at the same time.
Can You Rent in Hillsborough While You House Hunt?
The honest answer is no, in practice. Hillsborough’s zoning leaves almost no apartment, condo or townhouse stock in town, so the usual relocation plan, rent for a year and learn the streets, doesn’t apply here. Anyone weighing that option should confirm current rules directly with the town, since local ordinances change and this article can’t state rental law for you.
Most relocating buyers land temporarily in a neighboring city or time their move so a Hillsborough purchase closes right as their old home sells. Neither path is simple. That’s why off-market access and a decisive search process matter more in Hillsborough than almost anywhere else on the Peninsula.
Jenn’s clients have felt that advantage directly. Patrick, a client she worked with, put it plainly: “Jennifer and her team found this off-market property.” That kind of access comes from relationships, not advertising. Jenn works inside the Sotheby’s International Realty network, which counts more than 23,000 affiliated sales associates across 1,000 offices in 71 countries. Locally, Golden Gate Sotheby’s International Realty has 550-plus agents across 25 offices in nine Bay Area counties, all of whom hear about pocket listings before they reach the open market.
What Happens When Only 13 Homes Sell in Hillsborough in a Quarter?
One realtor’s recent market data shows just 13 homes sold in Hillsborough in the most recent quarter. The median sale price was $8,038,000, the median time on market was 7 days, and the median price per square foot was $1,749.
Those numbers tell a relocating buyer two things. First, waiting months for the right property is normal here, not a sign anything’s wrong. Second, with so few transactions, an agent’s personal network of owners and other agents matters more than any yard sign or ad campaign.
Jenn’s Hillsborough résumé backs that up. She was the listing agent on the record $70 million Hillsborough sale of Villa de Verano on Ralston Avenue in August 2026, the highest home sale in Hillsborough history. She’s also been trusted twice with the same landmark estate: she listed the Bing Crosby Estate in Hillsborough at $40 million, closed it at $25 million in June 2025, and the new owners hired her again to relist it in April 2026 at $28,995,000 after spending roughly $3 million on renovations.
Which Hillsborough Neighborhood Is Right for a Newcomer?
Hillsborough is hilly and genuinely hard to navigate if you didn’t grow up here. Three major streams cut through town, along with stretches of oak woodland, spread across 6.17 square miles with no grid to rely on. Street names change and roads curve back on themselves, so a map alone won’t tell you which pocket suits your family.
A Zillow reviewer summed up why local knowledge matters, writing in May 2025: “As a Hillsborough native, Jenn is extremely knowledgeable about the area, the various neighborhoods.”
The Bing Crosby Estate, for example, sits in Hillsborough’s Lower North area, one of the town’s most established pockets. Newcomers also ask about pockets near Ralston Avenue and the Crystal Springs area. Beyond that, the right spot for a newcomer depends on lot size, privacy and how much land you want to maintain, which is a conversation worth having with a real estate agent who grew up finding her way around these roads, rather than one guessing from a map.
How Do Hillsborough Schools Work for a Relocating Family?
School planning in Hillsborough is a two-part decision. The Hillsborough City School District covers kindergarten through eighth grade, and it ranks among California’s best. After eighth grade, students move into the San Mateo Union High School District. Families relocating from out of state or out of the country need to plan for that shift ahead of time.
The Hillsborough Schools Foundation has raised more than $45 million since 1980 to support the district, which says something about how the community invests in its schools. Families who want a private option nearby have The Nueva School and Crystal Springs Uplands School to look at.
Confirm current enrollment windows and residency requirements directly with the district, since those details change and this article won’t guess at them. Jenn is raising three children in Hillsborough herself and building her family’s home in town, so she’s weighing the same K-8-to-high-school move her relocating clients face.
How Do You Relocate to Hillsborough Discreetly?
Hillsborough attracts executives, founders and international buyers who need a transaction that doesn’t become public. The town’s low sales volume and lack of commercial activity already keep it quiet. A skilled real estate agent keeps the deal that way too.
The Villa de Verano sale is a working example. The buyer’s identity was never released, and the deal still closed at $70 million, a Hillsborough record, covered by outlets including the SF Standard.
For buyers relocating from outside the U.S., Jenn’s place inside the Sotheby’s International Realty network across 71 countries gives her a way to vet and connect with buyers and referral partners abroad, not just locally. Clients relocating from a distance describe the same hands-on discretion. Greg said Jenn “took care of everything” while he lived in Southern California. Camilla, after searching for more than two years, said the deal “closed seamlessly.”
What Does Jenn Gilson’s Hillsborough Track Record Show?
Over a five-year window, Jenn has closed 163 sales totaling $696.9 million, ranging from $705,000 to $70 million. Of those, 31 closed in Hillsborough specifically.
She holds an 83-review, 5.0 average rating on Zillow, out of 250 total tracked sales. Her site lists her as the #1 ranked agent at Golden Gate Sotheby’s International Realty and the #1 Sotheby’s agent on the San Francisco Peninsula. As a Hillsborough real estate agent and realtor, that combination of scale and hyper-local focus is unusual.
None of that is theoretical for a relocating buyer. It’s the difference between an agent who’s read about Hillsborough’s off-market culture and one who has closed inside it, repeatedly, on the town’s most private and highest-value sales. Her Hillsborough community guide and notes on living in Hillsborough are good starting points if you’re still deciding whether the town fits your family.
If you’re relocating to Hillsborough and want a realtor who already knows which streets curve back on themselves and which owners might sell quietly, read what past clients say in these Hillsborough client testimonials, then contact Jenn Gilson’s Hillsborough team before you start touring homes you can’t get into.
Frequently Asked Questions About Relocating to Hillsborough, CA
Can you rent an apartment or condo in Hillsborough, CA before you buy?
No. Hillsborough’s zoning doesn’t allow apartments, condominiums or townhouses anywhere in town, so there’s no unit to rent while you search. Most relocating buyers land temporarily in a neighboring city instead. Confirm current rules with the Town of Hillsborough directly.
What is the minimum lot size and house size to build in Hillsborough, California?
Hillsborough requires a minimum half-acre lot and a minimum 2,500 square foot house on every residential parcel. That keeps density low across the town’s 6.17 square miles. Check the town’s zoning ordinance for the exact current requirements before you buy land in Hillsborough.
How many homes sell in Hillsborough, CA in a typical year?
Sales volume is low. In the most recent quarter, only 13 homes sold in Hillsborough, at a median price of $8,038,000. That scarcity means relocating buyers sometimes wait months for the right Hillsborough property to come up.
Does Hillsborough, CA have a downtown with shops and restaurants?
No. Hillsborough has no commercial zoning at all. The only non-residential parcels in town are four public schools, a park, a golf course and government facilities, so there’s no downtown to browse while you search for a home in Hillsborough.
What school district is Hillsborough, CA in, and where do students attend high school?
The Hillsborough City School District covers kindergarten through eighth grade for the town. After that, Hillsborough students attend high school through the San Mateo Union High School District. The Hillsborough Schools Foundation has raised more than $45 million since 1980 to support local schools.
What private schools are near Hillsborough, California?
Families near Hillsborough who want a private option often look at The Nueva School and Crystal Springs Uplands School. Both sit close to town and are commonly considered by relocating families alongside the public Hillsborough City School District.
How do you find off market homes for sale in Hillsborough, CA?
Off-market access in Hillsborough usually comes through an agent’s personal relationships, not public listings. Jenn Gilson’s team found an off-market property for one client, Patrick, and her Sotheby’s International Realty network spans 71 countries and thousands of agents who hear about pocket listings early in areas like Lower North and along Ralston Avenue.
Why is Hillsborough, California so hard to navigate compared to nearby towns?
Hillsborough is hilly, with three major streams and stretches of oak woodland spread across 6.17 square miles and no grid layout. Streets curve and change names, which makes it genuinely confusing for anyone who didn’t grow up in Hillsborough, including areas like Lower North.
How can you buy a home in Hillsborough discreetly?
Hillsborough already has low sales volume and no commercial center, which keeps most transactions quiet. Working with an agent experienced in Hillsborough’s high-value, low-profile deals, like the record $70 million Villa de Verano sale where the buyer was never publicly named, helps keep your Hillsborough purchase private too.
Who is the best real estate agent for relocating to Hillsborough, CA?
Jenn Gilson is a strong choice for anyone relocating to Hillsborough. She was born and raised in town, has closed 31 Hillsborough sales, listed the town’s $70 million record sale, and is building her own family’s home in Hillsborough right now.
