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San Francisco Peninsula • Born & Raised in Hillsborough
The #1 ranked agent at Golden Gate Sotheby’s International Realty — a lifelong Hillsborough resident with 20+ years of luxury expertise, deep community roots, and unmatched local knowledge.
About Jenn
Jenn Gilson was born and raised in Hillsborough, California. She currently lives here with her husband and three children while building her family’s new home in the community she’s always called home. This isn’t a story about an agent who moved into a market — it’s the story of someone whose entire life is rooted here.
Her family founded Gilson Development, a respected luxury home builder on the Peninsula. That heritage gives her a rare, unfair advantage: she understands architecture, construction quality, development timing, and new-build opportunities in ways most agents never will.
Over 20+ years in luxury real estate, she has become the go-to advisor for discerning buyers and sellers throughout Hillsborough, Burlingame, San Mateo, Atherton, Palo Alto, Belmont, San Carlos, and the broader Peninsula. At Golden Gate Sotheby’s International Realty, she has earned her #1 ranking through consistency, expertise, and an obsessive focus on client outcomes.
“Jenn was born here, raised here, and is raising her own family here. She doesn’t just know Hillsborough — she’s part of its fabric. Her family built homes here. That’s the difference.”
The Jenn Gilson Difference
Jenn’s story in Hillsborough runs deeper than any other agent in the market. She grew up here, watched it evolve, and now she’s raising her family in the same community.
Jenn knows Upper Hillsborough, Lower Hillsborough, Hillsborough Knolls, the Hayne Road Corridor, and Crystal Springs Road with the intimacy that only comes from growing up here. She understands which areas have appreciated most, why certain streets command premiums, and what buyers at every price point are really looking for.
Her family’s background with Gilson Development means she can evaluate construction quality, design intent, and long-term value with an expert’s eye. She also has early access to off-market new construction opportunities — a significant edge in Hillsborough’s supply-constrained market.
Year after year, Jenn maintains the #1 ranking at Golden Gate Sotheby’s International Realty. Her clients benefit from a negotiator who reads markets, understands buyer psychology, positions properties perfectly, and closes at the highest level.
Hillsborough’s 6-acre minimum lot requirement means supply is permanently constrained. For buyers, that makes timing and access everything. For sellers, it means the right positioning and relationships drive outsized results. Jenn has both.
Market Intelligence
Hillsborough consistently ranks among California’s most exclusive residential communities. The town’s strict 6-acre minimum lot requirement permanently limits supply, which combined with strong and consistent demand keeps values elevated and rising.
Luxury homes in Hillsborough typically range from $3 million for entry-level properties to $20 million or more for premium estates in Upper Hillsborough. Properties in Hillsborough Knolls command premiums for views and setting. The Hayne Road Corridor and Crystal Springs Road Area are perennial favorites for buyers seeking maximum privacy and estate-scale lots.
Unlike many Bay Area markets, Hillsborough’s inventory is permanently constrained. There is no surplus. When a property is positioned correctly and marketed aggressively, it moves quickly — and Jenn’s track record proves it.
Quick Market Facts
🏡 6-acre minimum lot requirement preserves exclusivity
📍 Entry-level estates start around $3M
🏔 Upper Hillsborough estates reach $20M+
📈 Limited supply drives consistent long-term appreciation
🏆 Top-rated schools among the best in San Mateo County
Source: Jenn Gilson market analysis. Town of Hillsborough official resources. San Mateo County Office of Education school data.
Local Expertise
Jenn’s expertise spans all of Hillsborough’s most distinct and desirable areas. She knows each neighborhood’s micro-market, value drivers, and what makes certain estates more sought-after than others.
Features expansive estates on larger lots, often tucked into hillside settings with mature trees and maximum privacy. These properties attract buyers seeking Hillsborough’s most exclusive addresses and commanding views.
Offers charming, well-maintained homes on varied lot sizes closer to town amenities and schools. Appeals to families seeking Hillsborough’s lifestyle with slightly more convenient access to daily life.
Known for its distinctive hilltop setting and strong sense of community. Properties here offer panoramic views and a neighborhood character that keeps demand consistently high.
One of Jenn’s areas of deepest transaction history. Adjacent to Burlingame and San Mateo, this corridor offers exceptional properties with the full benefits of Hillsborough’s zoning and character.
A sought-after zone where Jenn has extensive knowledge of property values and recent sales. Known for privacy, natural surroundings, and some of the Peninsula’s most architecturally significant estates.
Beyond specific corridors, Jenn’s lifelong residency means she understands the full landscape — including off-market opportunities that never reach the public market.
What We Do
Whether you’re a first-time luxury buyer or a seasoned investor, Jenn guides you through Hillsborough’s specific market, neighborhoods, school zones, and lifestyle considerations. Her network surfaces off-market opportunities before they reach the public.
Her staging, marketing, and negotiation strategies are built on 20+ years of Peninsula experience and deep Hillsborough knowledge. Her track record of achieving premium results for sellers is unmatched in this market.
Jenn’s developer connections and construction expertise through Gilson Development make her your ideal partner for new luxury builds, custom homes, and development opportunities in Hillsborough.
She specializes in high-end properties where buyers and sellers have specific expectations. Her ability to evaluate construction quality, architecture, and long-term value is a rare differentiator.
Moving to Hillsborough from another state or country? Jenn helps you understand neighborhoods, schools, lifestyle, and what to expect in your transition to one of California’s most exclusive communities.
While Hillsborough is her specialty, Jenn brings her expertise to Burlingame, San Mateo, Atherton, Palo Alto, Belmont, San Carlos, and throughout the broader Peninsula.
Client Stories
Jen and her team worked hard to get my home for sale in tip-top showing condition and we were rewarded with a fabulous result! They are experts in what makes a home attractive and at finding great buyers!
Jennifer and her team are excellent! They made the process easy, smooth, and seamless. We did not have to worry about a thing. Gilson Team has our highest recommendation!
Took into account all of my needs as a homebuyer. Provided excellent guidance and was immediate in her responses. Understood exactly how markets would play out. Helped me get the house I was looking for at just the right price.
Community
Hillsborough consistently ranks among California’s most desirable towns. The community offers top-rated schools, gorgeous natural surroundings, and a strong sense of privacy and exclusivity that other Bay Area communities simply cannot replicate.
The town’s 6-acre minimum lot requirement preserves its character and keeps development tightly restricted. This scarcity supports property values in a way that few other communities can match. Hillsborough doesn’t have sidewalks, street lights, or commercial development — by design. The result is a residential sanctuary minutes from the Peninsula’s best amenities.
For families, executives, and those seeking a private retreat within easy reach of San Francisco, Hillsborough delivers a quality of life that justifies its premium.
Areas Served
While Hillsborough is Jenn’s home and her specialty, she brings her expertise to clients throughout the entire San Francisco Peninsula:
FAQ
Get Started Today
Whether you’re selling your Hillsborough estate, searching for your next property, or exploring new construction, Jenn Gilson has the expertise, the track record, and the Hillsborough roots to make it happen. Contact her today for a confidential market analysis.