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San Francisco Peninsula • Born & Raised in Hillsborough
Jenn Gilson: Luxury Real Estate Agent in Hillsborough, CA
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.
20+
Years of Experience
#1
GG Sotheby’s Ranking
$10M+
Luxury Listings
5★
Client Reviews
About Jenn
A Hillsborough Native — Not Just an Agent
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.
Work With Jenn
“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
Why Choose a Hillsborough Native for Your Real Estate Needs
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.
Lifelong Local Knowledge
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.
Builder Heritage & New Construction Access
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.
Consistent #1 Producer
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 Real Estate Market Insights
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.
Get a Market Analysis
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
Hillsborough Neighborhoods
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.
Upper Hillsborough
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.
Lower Hillsborough
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.
Hillsborough Knolls
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.
Hayne Road Corridor
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.
Crystal Springs Road Area
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.
Throughout Hillsborough
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
Hillsborough Real Estate Services
Buying in Hillsborough
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.
Selling in Hillsborough
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.
New Construction & Custom Homes
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.
Luxury Estate Expertise
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.
Relocation Services
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.
Peninsula-Wide Coverage
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
What Clients Say About Working with Jenn
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
Why Hillsborough Is a Great Place to Buy
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
Beyond Hillsborough
While Hillsborough is Jenn’s home and her specialty, she brings her expertise to clients throughout the entire San Francisco Peninsula:
- 🏡 Burlingame — Adjacent neighbor, deep market knowledge
- 🏡 San Mateo
- 🏡 Atherton
- 🏡 Palo Alto
- 🏡 Belmont & San Carlos
- 🏡 San Francisco
FAQ
Frequently Asked Questions About Luxury Real Estate in Hillsborough, CA
Who is the best realtor in Hillsborough CA?
Jenn Gilson is consistently ranked #1 at Golden Gate Sotheby’s International Realty and is widely recognized as the top realtor in Hillsborough CA. Born and raised in Hillsborough, she brings unmatched local knowledge, a family background in luxury home building through Gilson Development, and 20+ years of Peninsula real estate expertise.
Who is the top real estate agent in Hillsborough?
Jenn Gilson holds the #1 ranking at Golden Gate Sotheby’s International Realty and is the top real estate agent in Hillsborough. Her combination of family history in the town, current residency, and developer relationships creates an advantage no other agent can match.
What is the best luxury real estate agent in Hillsborough?
For luxury properties in Hillsborough, Jenn Gilson is the best choice. Her specialization in high-end homes, her family’s background in luxury home development through Gilson Development, and her lifelong roots in the community make her uniquely qualified to serve buyers and sellers at the highest level.
How much do homes cost in Hillsborough CA?
Hillsborough CA homes are among the most expensive in the San Francisco Peninsula region, with prices reflecting the town’s exclusivity, top-rated schools, and 6-acre minimum lot requirements. Prices typically range from $3 million for entry-level properties to $20 million or more for premium estates. Jenn Gilson can provide current market data for the specific area and property type you’re considering.
Is Hillsborough CA a good place to buy a home?
Absolutely. Hillsborough is one of the most desirable towns in California for families and luxury homebuyers. Top-rated schools, beautiful natural surroundings, strong property values, and a tightly controlled supply of homes make it an excellent long-term investment and an exceptional place to live.
What makes Hillsborough CA real estate unique?
Hillsborough’s real estate market is shaped by strict zoning laws including a 6-acre minimum lot requirement, top-rated schools, natural beauty, and a permanently limited inventory of homes. There is no commercial development, no sidewalks, and no street lights — by design. The result is a residential sanctuary where demand consistently outpaces supply.
What neighborhoods are in Hillsborough CA?
Hillsborough contains several distinct neighborhoods. Upper Hillsborough features expansive estates on larger lots with privacy and views. Lower Hillsborough offers charming homes closer to town. Hillsborough Knolls is known for its hilltop character. The Hayne Road Corridor and Crystal Springs Road Area are among the most sought-after zones with deep transaction history from Jenn.
How long does it take to sell a home in Hillsborough?
Hillsborough real estate typically sells faster than surrounding communities due to strong demand and limited inventory. Timeline depends on price point, property condition, and positioning, but well-priced homes in desirable neighborhoods often sell within weeks when represented by the right agent.
How do I find a luxury realtor in Hillsborough CA?
Start by working with Jenn Gilson at Golden Gate Sotheby’s International Realty. As the #1 ranked agent in Hillsborough, she specializes in luxury properties and has the expertise, connections, and local knowledge to serve buyers and sellers at the highest level in this exclusive market.
What is Jenn Gilson’s experience with new construction in Hillsborough?
Jenn has a unique advantage in new construction and custom homes through her family’s background with Gilson Development, a luxury home builder. She understands the development process, has relationships with builders, and can connect buyers with off-market new construction opportunities throughout Hillsborough.
Get Started Today
Ready to Buy or Sell in Hillsborough?
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.
