Born and raised in Hillsborough, California, Jennifer Gilson offers deep-rooted expertise in Peninsula and Silicon Valley real estate. With a strong background serving buyers, sellers, and investors across San Mateo and Santa Clara counties, she's known for her sharp negotiation skills, market insight, and personal discretion. Jennifer listens closely to her clients, tailoring every search or sale to align with their lifestyle and goals. Her Certified Relocation Specialist designation allows her to support national and international moves with ease, backed by a trusted network of resources.
Jennifer's real estate roots run deep — her family founded Gilson Development over a decade ago, a boutique builder known for custom homes across the region. Her hands-on experience with designers and developers helps clients spot opportunities early, even pre-construction. Recognized as a Top Producing Agent every year from 2013 to 2024, Jennifer is a trusted and consistent presence in the San Francisco Peninsula and Silicon Valley markets.
Welcome to 1950 Ralston
About Jennifer Gilson
Top Producing Agent | Golden Gate Sotheby's International Realty
Your Peninsula & Silicon Valley Expert
Jennifer specializes in high-demand communities where discretion, access, and timing matter most. With deep neighborhood insight and local relationships, she helps buyers and sellers move with confidence.
A Marketing Strategy Built to Drive Real Results
Every listing is supported by a bespoke marketing program engineered to reach the right buyers, generate genuine demand, and turn attention into offers.
A Dedicated Website for Every Residence
Jennifer builds a private, invitation-based website for each property, tracking engagement in real time: who is viewing, how often they return, and how long they spend exploring the home.
Recent examples include dedicated sites for 3000 Ralston Avenue and an in-progress site for 2265 Ralston as part of an off-market campaign. Every visit also captures the visitor's contact information, building a live, growing list of qualified buyer interest to act on.
Preview Website
Cinematic Storytelling That Sells
Nobody tells a property's story quite like Jennifer. For every residence, she creates high-impact content that generates qualified interest and builds real excitement, and it works: her videos produce real showings, real inquiries, and real offers. The highest-priced buyer she has represented came directly through this marketing and her network. A few examples of the approach:
Top Agent Collaboration Reel
A national reel produced with fellow top female agents that earned more than 15,000 views. It carries a property well beyond the local market to qualified buyers nationwide. Jennifer is now creating versions with agents at new-construction projects across the country.
Designer & Agent Luncheon
A spring fling networking luncheon Jennifer hosted inside the residence itself. Bringing designers and agents together in the space lets them experience the property first-hand and build connections around it. The video captures that energy and carries it to a wider audience.
New-Construction Agent Event
A stalled new-construction listing had seen no pre-market activity. Jennifer stepped in and hosted a catered event with 200-plus agents and five panelists from Santa Barbara, Los Angeles, and the Peninsula. An offer was accepted in under seven days.
Holiday Teaser for a Takeover Listing
A holiday teaser that shows the property in a real, lived-in setting rather than as an empty listing. Reflecting the time of year makes the home feel relatable and easy to picture living in. Season and setting do the work.
The Bing Crosby Estate Teaser
A visual walkthrough of the estate once owned by legendary entertainer Bing Crosby. It moves through the property to capture the history and legacy behind it, letting the setting speak for itself. That sense of legacy is what drove more than 20 million views across social media.
Villa de Verano Record Sale
The reel marking a $70,000,000 sale, the highest in Hillsborough's history and Northern California's top sale of 2026. It shows how cinematic marketing and the right network combine to produce a record result.
Under-Construction Update
Recorded during the construction phase of a $19,500,000 residence, with the interior designer walking through the reasoning behind every detail. It gives buyers an inside view of the process and the choices shaping the home, building interest well before completion.
Marketing in Action: 2265 Ralston Avenue
ViewA look at what Jennifer has put in place so far for 2265 Ralston Avenue. Inside are three videos from the campaign to date.
Villa de Verano
Highest Sale Ever in Hillsborough
3000 Ralston Avenue
Hillsborough
$70,000,000
Villa de Verano at 3000 Ralston Avenue has officially sold for $70,000,000, more than doubling Hillsborough's previous residential sales record and marking Northern California's highest residential sale of 2026.
A Record of Success
Social Virality
The Bring Crosby Estate reached 20+ Million Views On Social Media
Globally Recognized
Jenn has represented properties featured in The Wall Street Journal, Realtor.com, SFGate, People.com, The Real Deal, ABC7 News, and many more
Record-Breaking Sale
Jenn's $70M sale of Villa de Verano set a new Hillsborough record and became Northern California's highest sale of 2026
Proven Success in the Peninsula's
Most Coveted Neighborhoods
Jennifer has represented record-breaking sales across Hillsborough, Palo Alto, and surrounding communities — including both public and private transactions.
Step Inside the Extraordinary
Discover cinematic tours of our most coveted residences—crafted to captivate, designed to inspire.
Villa de Verano
The Bing Crosby
165 Woodridge
Verified Member of Top Agent Network
Jennifer is part of an invite-only network of top-producing agents. Only 1 in 10 qualifies.
Ability to test market your home and price with less hassle and without it becoming stale on the MLS.
Access to pre-qualified and highly motivated buyers.
Access to a community of proven agents whose collective experience allows deals to happen quickly, reliably, and often privately.
Referrals to the proven best service providers in your area.
Founder of The Key Women Community
Jennifer is the founder of Key Women, a global collective of women rooted in the home ecosystem, unlocking potential through collaboration, innovation, and community.
She recently hosted the community at one of her Hillsborough listings, bringing together top realtors, financial advisors, architects, and interior designers from across the country.
A Home Featured
in Print
Jennifer publishes a magazine for the Hillsborough community each month. A listing is featured across its pages and delivered straight to the neighborhood's most active buyers and sellers.
Teaser videos
Behind-the-scenes footage
Guided video walk-throughs
Ongoing updates through the sale
Engaged Instagram followers
Strategic Marketing Across Every Platform
Jennifer builds campaigns that carry a property across every platform through story-driven content.
With more than 14,400 engaged Instagram followers, Jennifer builds visibility from the moment a listing goes off-market through the close of escrow, keeping an active audience watching for what comes next.
It's All About the Views
Sotheby's International Realty is the most-watched real estate brand on YouTube:
193M+
Global Video Views
412K+
Subscribers
#1
in Real Estate Video Viewership
Leveraging the Full Reach of Sotheby's
Sotheby's International Realty offers unmatched global reach, and Jennifer actively puts it to work. Recently recognized at the Top 100 Sotheby's Dinner in New York, she has also served as a featured panelist in Hawaii, Las Vegas, and New York, presenting listings directly to top agents around the world. Few agents invest the same effort in connecting with local and international agents alike, and that network translates into maximum exposure for every listing.
Watch the Hawaii Networking EventYour Home, Marketed Worldwide
Listings are published on over 100 global platforms and premium media outlets including:
SALES ASSOCIATES
OFFICES
COUNTRIES
in annual global referrals
Off Market Strategy
Through a combination of my strategic online presence and trusted, behind-the-scenes relationships, I generate real, qualified interest—discreetly. There is a proven way to market confidentially while still sharing compelling teasers with select high-level contacts, creating curiosity without compromising privacy.
Off Market → Password Protected Estate Website → Video Content → Internal Network → Sotheby's Global Network and Exposure → On Market (Full Press + Public Video Marketing)
Private, Vetted Showings Only
Each private tour will be scheduled only after the prospective party has viewed the exclusive landing page and been vetted as a qualified contact. All showings will be discreet, intentional, and curated.
What Sets Jennifer Apart
A mother of three and deeply rooted in the community, Jennifer knows exactly who is buying in Hillsborough right now and how to achieve the highest possible price. She brings a hands-on, strategic approach to every listing and is fully committed to delivering the strongest possible result, backed by one of the strongest agent networks in the Bay Area and nationally.
In Conclusion
I Look Forward to Offering You Several Unique Advantages
While real estate by nature is local, the market for your home is truly national — and increasingly global. Sotheby's International Realty is part of this global network, with offices in the world's most sought-after locations.
Selecting me and Golden Gate Sotheby's International Realty to represent your property connects you to professionals known for their quality, service, and local expertise. We are deeply tied to the communities we serve, and we're committed to exceeding the expectations of today's most discerning buyers and sellers.
You'll Benefit From:
Preeminent local expertise and contacts
Access to proprietary marketing materials
Strong brand recognition and industry relationships
A referral network of top agents worldwide
Strategic internet and global marketing
Cross-marketing with Sotheby's Auction House
The white-glove service Sotheby's is known for
The backing of a legacy brand trusted globally
A proven ability to sell across all price points