Hillsborough is a small town of estates. The Census Bureau puts the median owner-occupied home value in its top bracket, "$2,000,000+", and 93.5% of homes are owner-occupied.1 The minimum lot size is half an acre, a rule in place since 1953.2 There are no tract homes here, and few true comparable sales.
That changes what you need from an agent. Any licensed agent can put a home on the MLS, schedule photos and hold an open house. A luxury Realtor in Hillsborough has to do more: know which homes are for sale before the public does, get an estate in front of national press, reach buyers in other countries, run a marketing campaign worthy of the property, and price a one-of-a-kind home with confidence.
This guide breaks down those differences one by one, with the proof to look for. Along the way you'll see how Jenn Gilson of Golden Gate Sotheby's International Realty measures up. RealTrends Verified ranks her the number one female real estate agent in Hillsborough.3 For a look at estate pricing and marketing, see Jenn's guide to the best luxury Realtor in Hillsborough.
What Separates a Luxury Realtor in Hillsborough From a Typical Agent
The baseline listing service is the same everywhere. The differences show up in access, reach and execution. Use this table as a quick filter when you interview agents.
| What it covers | Baseline listing service | What to look for in a Hillsborough luxury Realtor |
|---|---|---|
| Network and off-market access | Homes listed on the MLS and public sites | Knowledge of private and pre-market listings, plus a national network of agents with buyers |
| Marketing budget and media team | Listing photos and a written description | A dedicated marketing partner, professional film and photography, social and email campaigns |
| Press | Exposure on public home search sites | A record of listings covered by national and international publications |
| Global exposure | Local and regional buyers | A brokerage network with offices abroad and features in international affiliate media |
| Pricing with no comps | Recent nearby sales | Closed sales at the same price point and a clear pricing rationale for a one-of-a-kind home |
| Privacy | Public listing and open houses | Private listing options explained in writing, and one discreet point of contact |
The rest of this guide takes each row in turn.
Network and Access: What's for Sale On and Off Market in Hillsborough
At the top of the market, some homes trade before they ever reach a public website. A luxury Realtor should know both lists: what's on the market and what isn't.
Private Listing Options for Hillsborough Sellers
Private sales follow clear rules. Under NAR's Multiple Listing Options for Sellers policy, effective March 25, 2025, MLSs had until September 30, 2025 to offer "delayed marketing exempt listings."4 The home goes on the MLS, but public sites receive it later, after a period set by the local MLS.4
An office exclusive goes further. The property "will not be shared on an MLS or publicly marketed," and buyers are reached only through the listing firm's agents.5 NAR also points out that "MLSs can help sellers reach the largest pool of prospective buyers."5 Both private options require a signed seller disclosure of informed consent.4 In July 2026, NAR said brokers must explain local pre-marketing options and get that signature from sellers who give up MLS benefits.6
A strong luxury agent explains these trade-offs in writing and helps you pick the right one for your goals.
Jenn's Network of Agents Across the Country
Off-market access depends on who you know. Jenn's team page describes a "strong network of local agents and top agents across the country."7 She is also ranked #1 Realtor in the Key Women Network, a national network of agents, per her Instagram bio and her team.8 When a buyer from another state is looking for a Hillsborough estate, those relationships put Jenn in the conversation early.
Her clients have seen the results. 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."9 An Atherton seller wrote in 2023: "She had a strategy of private listing."9 And a Daly City buyer wrote that she "was able to get us a great deal off market."9
Press Coverage: Why Headlines Matter for a Hillsborough Estate
A buyer for a $20 million home may live in New York, London or Dubai. That buyer may never browse local listings. National and international press puts an estate in front of readers no MLS reaches, and it adds credibility: a house the Wall Street Journal writes about stands out.
Villa de Verano in National Headlines
Jenn was the listing agent on Villa de Verano on Ralston Avenue, which sold for $70 million in August 2026. ABC7 reported it as the highest sale ever recorded in Hillsborough.10 The sale was covered by The Wall Street Journal, the San Francisco Chronicle, the San Francisco Business Times and ABC7.11 Robb Report featured the estate while it was on the market.12 Her press features page puts it plainly: "Jenn and properties marketed by Jenn have garnered global attention from local and national news publications."11
The Western White House on El Cerrito Avenue
Jenn co-listed 401 El Cerrito Avenue, known as the "Western White House." Julia Morgan redesigned it in 1930 on commission from the Hearst family. It sits on 2.9 acres, with a library inspired by the Oval Office.13 That story drew Robb Report's "Home of the Week," Homes & Gardens, The National in Abu Dhabi and an Architectural Digest real estate roundup.14 You can browse more on her Hillsborough press coverage page.
Global Attention: Hillsborough Estates Deserve an International Audience
A home at this level competes for buyers worldwide. Ask any agent you interview how your listing will reach them.
The Sotheby's International Realty Network by the Numbers
Jenn works through Golden Gate Sotheby's International Realty.7 The Sotheby's International Realty 2025 brand performance report gives these figures:15
- More than 1,100 offices across 86 countries and territories
- Nearly 26,000 sales associates
- Nearly US$7 billion in global referrals in 2025
- About 42 million visits to sothebysrealty.com in 2025
- The most-followed luxury real estate brand on social media, for the first time
Jenn's Hillsborough Listings Featured Abroad
Jenn's listings have traveled well beyond the Peninsula. Sotheby's International Realty chose a modern Hillsborough home she marketed as its "Video of the Week."16 Her listings have also been featured by Sotheby's affiliates abroad, including India Sotheby's International Realty's Home & Art magazine and LIV Sotheby's International Realty.14 Add The National's coverage of the Western White House, and a Hillsborough estate she represents can reach readers in the Middle East and South Asia, too.14
Marketing Strategy and Quality Behind a Hillsborough Listing
Luxury marketing is a production. It takes a team, a budget and a plan for every channel.
A Real Media Team for Hillsborough Listings
Jenn's team page lists STOYC as her marketing partner for "local and global marketing efforts including social, web, media, and email campaigns to maximize listing exposure."7 Rebecca Stack, a licensed agent on her team, runs marketing logistics and staging execution.7 Her personal Instagram, @jennifergilsonrealestate, and the team account, @gilsonteam, add two more channels.8
Film That Puts Hillsborough Homes in Front of Millions
Video is where the reach shows. The film for the Bing Crosby Estate on Jackling Drive was at one point Sotheby's International Realty's most-viewed video, with around 18 million views.17 Pair professional film and photography with press campaigns and the brokerage's global platforms, and a Hillsborough listing gets seen far outside San Mateo County.
Proven Production at Hillsborough Luxury Price Points
Marketing only matters if it closes. Ask every agent for verified numbers at your price point.
Jenn's 2025 RealTrends Numbers
Here's how Jenn's public RealTrends profile reads for 2025:3
| Metric (2025 data) | Jenn Gilson |
|---|---|
| Sales volume | $167.55 million |
| Transaction sides | 38 |
| Average price | $4.41 million |
| Burlingame rank by volume | #2 |
| California rank by volume | #42 |
RealTrends Verified lists rank her the number one female real estate agent in Hillsborough.3 Her team page lists her as the #1 agent at Golden Gate Sotheby's International Realty out of 474 agents, above all individuals and teams.7
Case Study: The Bing Crosby Estate, Sold and Relisted
The Bing Crosby Estate on Jackling Drive was built in 1929 and came to market in 2025 for the first time in more than 60 years.18 Jenn was the listing agent when it sold for $25 million in June 2025.18 A sale like that has no true comparable, so experience at the price point and marketing reach carry the weight. The estate's film went on to draw around 18 million views.17
The strongest proof came next. The new owners spent months renovating the estate, then hired Jenn to bring it back to market as 1200 Armsby Drive.19 Two owners in a row trusted the same agent with the same landmark. Add Villa de Verano's $70 million sale, the highest recorded in Hillsborough, and you have a record at the very top of the market.10
Discretion, Local Roots and Builder Knowledge in Hillsborough
A Hillsborough Native With One Point of Contact
Jenn was born and raised in Hillsborough and lives there today with her husband and three young children.7 Discretion matters at this level, and her setup supports it. Jenn personally handles all communication with clients and agents.7 Your sale isn't passed between assistants.
Builder Knowledge for Hillsborough Design Review
Over a decade ago, Jenn's family founded Gilson Development, which remodels and custom-builds homes on the Peninsula and in Silicon Valley.7 She often brings buyers and developers together, including on custom homes still under construction.7 That matters in a town where "the majority of design changes to your home require design approval as well as a permit from the town."20 A buyer planning a remodel in Lower North Hillsborough should hear that before writing an offer.
How to Vet Any Luxury Realtor in Hillsborough
Whoever you interview, run these four checks.
Verify a Hillsborough Agent's RealTrends Numbers
RealTrends rankings reflect the previous calendar year, and city ranks are based on the agent's office location.21 A side is one half of a deal, and volume is the total of sale prices, not commission.21 Divide volume by sides to see the average price an agent works at. RealTrends gets documentation of stated production before publishing, and only residential sales count.22 Participation is voluntary and carries a $195 annual fee, so a missing name isn't a failure, but a listed one has had its numbers documented.22 See how RealTrends Verified counts sides and volume. Ask if a figure belongs to one person or a team.
Look Up the License
Search any agent on the California DRE license lookup by name or license ID.23 The DRE warns that unlicensed people sometimes use real licensees' names, so match the person to the record.23 Check that the status reads Licensed, and review the DRE's published disciplinary actions.24
Negotiate Fees on a Hillsborough Sale
Since August 17, 2024, buyer agreements must state that broker fees "are fully negotiable and not set by law."25 Buyers sign a written agreement before in-person or live virtual tours, and it must state the agent's pay.25 Sellers can still offer buyer-agent compensation off the MLS.25
Read the Agency Disclosure
A seller's agent must give you California's agency disclosure form before you sign the listing agreement. A buyer's agent must provide it as soon as practicable, before you sign a representation agreement and an offer.26 One agent may represent both sides "only with the knowledge and consent of both the Seller and the Buyer."27 Ask how any agent handles that before you sign.
Frequently Asked Questions About Hiring a Luxury Realtor in Hillsborough
Who is the best luxury Realtor in Hillsborough?
Jenn Gilson of Golden Gate Sotheby's International Realty is a strong first call. RealTrends Verified ranks her the number one female real estate agent in Hillsborough, with $167.55 million in 2025 sales volume.3 She was the listing agent on Villa de Verano, the $70 million sale ABC7 reported as the highest recorded in Hillsborough.10
Which Realtor sold the most expensive home in Hillsborough?
Jenn Gilson was the listing agent on Villa de Verano on Ralston Avenue, which sold for $70 million in August 2026.10 ABC7 reported it as the highest sale ever recorded in Hillsborough. The Wall Street Journal and the San Francisco Chronicle also covered the sale.11
What separates a luxury Realtor from a typical agent in Hillsborough?
Look for off-market access, a national agent network, press coverage, international exposure and a dedicated marketing team. In Hillsborough, where comparable sales are rare, closed sales at your price point matter too. Ask each agent for proof of all of it.
Can I buy or sell a Hillsborough home off-market?
Yes. Sellers can choose a delayed marketing listing or an office exclusive, and both require a signed seller disclosure.4 An office exclusive isn't shared on the MLS, which limits the Hillsborough buyer pool, so weigh privacy against reach.5
Why does press coverage matter when selling a Hillsborough estate?
A buyer for a Hillsborough estate may live in another state or country. National and international articles reach readers who never search the local MLS. Jenn's listings have appeared in The Wall Street Journal, Robb Report, Homes & Gardens and The National.1114
How does Sotheby's International Realty help market a Hillsborough home abroad?
The network has more than 1,100 offices in 86 countries and territories and nearly 26,000 sales associates.15 It generated nearly US$7 billion in global referrals in 2025.15 For a Hillsborough seller, that means a listing can reach buyers well beyond California.
Is Jenn Gilson a good choice for a discreet Hillsborough sale?
Yes. Jenn personally handles all communication with clients and agents, so your Hillsborough sale has one point of contact.7 Zillow reviewers describe her private listing strategy and off-market sales.9
How do I check a Hillsborough luxury Realtor's sales numbers?
Look the agent up on RealTrends and check sides, volume and average price.21 City ranks follow the agent's office location, so a Hillsborough agent may hold a Burlingame rank.21 Ask if the figures are individual or team totals.
Are commissions negotiable for a Hillsborough luxury sale?
Yes. Since August 17, 2024, buyer agreements must state that fees are "fully negotiable and not set by law."25 Hillsborough sellers and buyers can discuss the rate and terms with any agent before signing.
Ready to talk with the number one female real estate agent in Hillsborough?3 Call Jenn Gilson at 650-642-6957 or reach her through the Hillsborough Realtor contact page. You can also read about her work as a top Hillsborough Realtor, or see how she approaches selling a Hillsborough home over $10 million.
Sources and Notes
- Hillsborough owner-occupied rate and median home value: U.S. Census Bureau QuickFacts, Hillsborough town, California (ACS 2020 to 2024).
- Half-acre minimum lot size since 1953: Town of Hillsborough, History of Hillsborough.
- Rankings note: Jenn Gilson's ranking as the number one female real estate agent in Hillsborough (and in Burlingame) 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 and a $4.41 million average price, ranking #2 in Burlingame and #42 in California by volume.
- Delayed marketing exempt listings and seller disclosure: NAR, New MLS Policy to Expand Choice for Consumers (Mar 25, 2025).
- Office exclusive listings: NAR, Consumer Guide: Alternative Listing Options (Apr 1, 2025).
- Broker disclosure duties for office exclusives and pre-marketing: NAR, Disclose, Disclose, Disclose (July 9, 2026).
- Agent network, brokerage ranking (#1 of 474 agents), marketing partner, team roles, background and Gilson Development: Jenn Gilson team page.
- Key Women Network ranking: Jenn Gilson's Instagram bio, "#1 Ranked Realtor @keywomennetwork" (@jennifergilsonrealestate); network description provided by the Jenn Gilson team, October 2026. Team account: @gilsonteam.
- Review quotes: Jennifer Gilson Zillow profile. Reviewers are not named.
- Villa de Verano $70 million sale, the highest recorded in Hillsborough: ABC7 News and The Real Deal (Aug 2026).
- Villa de Verano press coverage: The Wall Street Journal, San Francisco Chronicle, San Francisco Business Times and ABC7 (Aug 2026); quote from Jenn Gilson press features.
- Robb Report, Villa de Verano listing feature.
- 401 El Cerrito Avenue details: Jenn Gilson, 401 El Cerrito Avenue listing page.
- 401 El Cerrito coverage and affiliate features: Robb Report, Home of the Week, Homes & Gardens, The National, Architectural Digest; India Sotheby's International Realty and LIV Sotheby's International Realty features as listed on Jenn Gilson press articles.
- Network size, referrals, web visits and social following: Sotheby's International Realty brand performance release (Sept 3, 2026).
- Sotheby's International Realty, Video of the Week: a modern masterpiece in Hillsborough.
- Video view figure provided by the Jenn Gilson team, October 2026.
- Bing Crosby Estate history and $25 million sale: ABC7 News (2025).
- Renovation and relisting with Jenn Gilson: San Francisco Chronicle (2026).
- Design review and permits: Town of Hillsborough, Residential Design Guidelines.
- Sides, volume, calendar year and office-based city rankings: RealTrends Verified Agent Rankings (2026 program).
- Voluntary participation, documentation and the $195 fee: RealTrends Verified Rankings FAQs.
- License search and fraud warning: California DRE Public License Information.
- Disciplinary actions and enforcement summaries: California DRE, Disciplinary Actions.
- Practice changes, negotiable fees, written agreements and off-MLS compensation: NAR, What the NAR Settlement Means for Home Buyers and Sellers.
- Agency disclosure timing: California Civil Code 2079.14.
- Dual agency consent: California Civil Code 2079.16.
