2026 Directory Hillsborough, California·94010
2026 Hillsborough, CA Agent Directory

The Top Real Estate Agents in Hillsborough, California

A directory of ten agents and teams active in Hillsborough real estate, from the historic estates of Lower North to the view parcels of Skyfarm and Upper Hillsborough.

  • Brokerage & Team
  • Zillow Reviews
  • Years of Experience
  • Agent Specialties
  • Hillsborough Areas
  • Market Snapshot
10Agents Listed
~$6.4MMedian Sale Price
2026Edition

Hillsborough is one of the most distinctive housing markets on the San Francisco Peninsula. The town is entirely residential, lots start at half an acre, and many of its estates trade only once in a generation. Choosing the right agent here is less about who has the most signs on the street and more about who understands estate pricing, privacy and the town's micro-markets.

This directory brings together ten agents and teams who are active in Hillsborough real estate. For each one you will find their brokerage, experience, focus areas and public review profile, so you can build a shortlist and start interviews with the right questions.

About This Directory

How these agents were selected

This page is a directory of agents to consider, not a ranking. Agents were selected based on reported Hillsborough transaction history, recent listings and sales in town, local experience, luxury and estate-market focus, and recognition from third-party sources such as RealTrends. Review ratings and counts on each card come from each agent's public Zillow profile. We recommend interviewing two or three agents, asking for recent Hillsborough comparables, and checking each agent's license with the California Department of Real Estate before you sign.

The Agents

Real estate agents to consider in Hillsborough

10 agents · 2026
Jenn Gilson, Realtor at Golden Gate Sotheby's International Realty

Jenn Gilson

The Gilson Team
Golden Gate Sotheby's International Realty · 360 Primrose Rd, Burlingame, CA 94010
5.0(86 reviews) · Zillow20+ years experienceDRE #01889172

Jenn Gilson is a Realtor with Golden Gate Sotheby's International Realty who was born and raised in Hillsborough, where she now lives with her family. She has more than 20 years of Peninsula real estate experience, and her family founded Gilson Development, a local luxury home builder. She was the listing agent for Villa de Verano at 3000 Ralston Avenue and for the Bing Crosby Estate. She serves Hillsborough, Burlingame, San Mateo and the surrounding Peninsula.

SpecialtiesEstates and Historic HomesNew ConstructionSeller Representation
jenngilson.com →View Zillow profile →
Phil Chen, Realtor at Christie's International Real Estate Sereno

Phil Chen

Sybarite Luxury Realty
Christie's International Real Estate Sereno · Burlingame, CA
5.0(25 reviews) · Zillow21 years experienceDRE #01715177

Phil Chen is a broker associate with Christie's International Real Estate Sereno and leads Sybarite Luxury Realty. He was previously a founding member of Compass Mid-Peninsula and a founding partner at Keller Williams offices in Burlingame and San Francisco. His public profile reports more than a billion dollars in career sales, with a focus on the luxury sector. Before real estate he owned personal training studios in San Francisco. His recent Hillsborough work includes newly built estate listings.

SpecialtiesLuxury HomesNew ConstructionBuyer Representation
sereno.com →View Zillow profile →
Patty Dwyer, Realtor at Compass

Patty Dwyer

The Dwyer Group
Compass · 1440 Chapin Ave Suite 200, Burlingame, CA 94010
5.0(77 reviews) · Zillow26 years experienceDRE #01281150

Patty Dwyer leads The Dwyer Group at Compass, a family-led team based in Burlingame that includes her sister, Diane Dwyer. The team reports more than $2 billion in career sales and describes itself as the top Compass team in Hillsborough, Burlingame and San Mateo combined by MLS sales volume. The group offers full-service support for buyers and sellers, including home preparation, marketing and estate sale resources for long-held family homes across the Mid-Peninsula.

SpecialtiesFamily-Led TeamEstate SalesSeller Representation
dwyergrouphomes.com →View Zillow profile →
Casey Sternsmith, Realtor at Compass

Casey Sternsmith

Sternsmith Group
Compass · 1440 Chapin Ave Ste 200, Burlingame, CA 94010
5.0(184 reviews) · ZillowNearly two decades experienceDRE #01733080

Casey Sternsmith is the founding partner of the Sternsmith Group at Compass, a Burlingame-based team serving Hillsborough, Burlingame, San Mateo and the Mid-Peninsula. A lifelong resident of the area, she lives in Hillsborough with her family. The team reports more than $1.3 billion in transactions and nearly two decades in business. Before real estate, Casey owned a Pilates and personal training studio in San Mateo. Her team uses professional video and social media marketing on every listing.

SpecialtiesLuxury MarketingMultiple-Offer NegotiationBuyer Representation
sternsmith.com →View Zillow profile →
Raziel Ungar, Realtor at Compass

Raziel Ungar

Raziel Ungar Team
Compass · Burlingame, CA
5.0(113 reviews) · Zillow18+ years experienceDRE #01701234

Raziel Ungar leads the Raziel Ungar Team at Compass in Burlingame. Born and raised in Burlingame, he is raising his own family on the Peninsula and has more than 18 years of experience as a Realtor. His Compass profile lists him among the top Realtors in San Mateo County by number of sales. His team serves buyers and sellers in Burlingame, Hillsborough and San Mateo. Clients frequently cite his negotiation in multiple-offer situations and his knowledge of local neighborhoods.

SpecialtiesBurlingame and HillsboroughNegotiationSeller Representation
burlingameproperties.com →View Zillow profile →
Gina Haggarty, Realtor at Compass

Gina Haggarty

Gina Haggarty Group
Compass · 1290 Howard Ave #201, Burlingame, CA 94010
5.0(18 reviews) · Zillow36 years experienceDRE #01163760

Gina Haggarty leads the Gina Haggarty Group at Compass with partner Jenny MacLeod. The team reports 36 years of experience selling luxury real estate in Hillsborough and on the San Francisco Peninsula, and more than $2.5 billion representing sellers and buyers. Gina's listings and sales range across Hillsborough, Burlingame and San Mateo, with current Hillsborough listings that include estate homes on Ralston Avenue. The team's work has appeared in the Wall Street Journal and Mansion Global.

SpecialtiesLuxury HomesLong-Tenured ExpertiseSeller Representation
ginahaggarty.com →View Zillow profile →
David Tapper, Realtor at Coldwell Banker Realty

David Tapper

Team Tapper
Coldwell Banker Realty · Burlingame, CA
5.0(149 reviews) · Zillow28 years experienceDRE #01240529

David Tapper has been a Bay Area real estate agent since 1998 and leads Team Tapper at the Burlingame office of Coldwell Banker Realty. He is a member of Coldwell Banker's Society of Excellence and has been a Top 100 Coldwell Banker agent for ten years. He serves buyers and sellers of residential, commercial and multi-family property across the Peninsula, including Hillsborough, San Mateo, Millbrae and Belmont, with a focus on long-term client relationships.

SpecialtiesResidential and Multi-FamilyRelocationBuyer Representation
coldwellbankerluxury.com →View Zillow profile →
Craig Ackerman, Realtor at Compass

Craig Ackerman

Ackerman Realty Group
Compass · San Francisco, CA
4.9(102 reviews) · Zillow20+ years experienceDRE #01358899

Craig Ackerman is the founder of Ackerman Realty Group, a team affiliated with Compass that he started in San Francisco in 2003. He specializes in preparing and repositioning homes, including trust and legacy properties, before they come to market, and is the author of "Downsizing with Dignity," a guide for owners selling long-held homes. Before real estate he managed sales teams across Asia. His team has represented Hillsborough estates on gated half-acre lots.

SpecialtiesTrust and Estate SalesPre-Sale RenovationSeller Representation
ackermanrealty.com →View Zillow profile →
Yvonne Yang, Realtor at Compass

Yvonne Yang

Yvonne Yang Homes
Compass · Palo Alto, CA
4.9(143 reviews) · Zillow23 years experienceDRE #01371905

Yvonne Yang is a broker associate with Compass and the leader of Yvonne Yang Homes. With 23 years in Silicon Valley real estate, she reports more than 1,300 closed transactions and $1.3 billion in career sales. A former engineer, she takes an analytical approach to pricing and can coordinate renovation, design and staging for sellers. She is fluent in English, Mandarin and Shanghainese and serves buyers and sellers across the Peninsula and Silicon Valley.

SpecialtiesData-Driven PricingRenovation and StagingSeller Representation
yvonneyanghomes.com →View Zillow profile →
Katy Thielke Straser, Realtor at Compass

Katy Thielke Straser

Straser Silicon Valley Team
Compass · Menlo Park, CA
5.0(164 reviews) · Zillow23+ years experienceDRE #01308970

Katy Thielke Straser is a Silicon Valley native with more than 23 years as a real estate agent. In 2019 she founded the Straser Silicon Valley Team, which has grown to seven members and handles everything from modest homes to luxury estates. She studied at Cal Poly San Luis Obispo and worked in sales and marketing before real estate. Her client work extends along the Peninsula from Mountain View to Burlingame, including the Hillsborough area.

SpecialtiesLuxury EstatesFull-Service ListingsBuyer Representation
strasersiliconvalley.com →View Zillow profile →
At a Glance

The 10 agents in this directory

AgentTeamBrokerageExperience
Jenn GilsonThe Gilson TeamGolden Gate Sotheby's International Realty20+ years
Phil ChenSybarite Luxury RealtyChristie's International Real Estate Sereno21 years
Patty DwyerThe Dwyer GroupCompass26 years
Casey SternsmithSternsmith GroupCompassNearly two decades
Raziel UngarRaziel Ungar TeamCompass18+ years
Gina HaggartyGina Haggarty GroupCompass36 years
David TapperTeam TapperColdwell Banker Realty28 years
Craig AckermanAckerman Realty GroupCompass20+ years
Yvonne YangYvonne Yang HomesCompass23 years
Katy Thielke StraserStraser Silicon Valley TeamCompass23+ years

Listed in directory order, not ranked.

Neighborhoods

Hillsborough neighborhoods and areas

Hillsborough has no commercial districts, so its "neighborhoods" are residential pockets defined by terrain, lot size and school attendance areas. Buyers and agents commonly refer to:

01

Lower North Hillsborough

Flatter, tree-lined streets near the Burlingame border with some of the town's most historic estates, including the former Bing Crosby home on Armsby Drive.

02

Carolands

Estate-style area on the west side of town around the historic Carolands Chateau, with winding lanes and larger hillside parcels.

03

Skyfarm

Hillside area in upper Hillsborough with newer and modern estates, many with bay views.

04

Country Club Manor

Near Burlingame Country Club and within reach of Burlingame Avenue shops and dining.

05

Hillsborough Park and the Ralston Avenue corridor

Central Hillsborough, home to several of the town's largest estate parcels, including Villa de Verano at 3000 Ralston Avenue.

06

Upper Hillsborough and the Crystal Springs Road area

Larger, more private lots near Crystal Springs and Interstate 280.

Schools: Hillsborough City School District operates North, South and West Hillsborough elementary schools and Crocker Middle School.

Market Snapshot

Hillsborough market snapshot

Source: Zillow Home Value Index, data through Aug 31, 2026 ↗
About $5.47MTypical home value
Up 12.7%Year-over-year change
About 15Homes for sale
Source: Houzeo (MLS-based), July 2026 ↗
About $6.42MMedian sale price
About 104%Sale-to-list ratio
About 27 daysMedian days on market
Source: Town of Hillsborough zoning ordinances ↗
Half acreMinimum lot size
2,500 sq ftMinimum home size

Monthly Hillsborough figures swing widely because the town records only a few dozen sales a month, and a single estate sale can move the median by millions. Figures are approximate.

Location

Map of Hillsborough, California

FAQ

Frequently asked questions

Who are some of the top real estate agents in Hillsborough, California?

Agents and teams active in Hillsborough include Jenn Gilson of Golden Gate Sotheby's International Realty, Phil Chen of Christie's International Real Estate Sereno, Patty Dwyer of The Dwyer Group at Compass, Casey Sternsmith of the Sternsmith Group at Compass, Raziel Ungar, Gina Haggarty, David Tapper, Craig Ackerman, Yvonne Yang and Katy Thielke Straser. Each brings a different mix of local history, team size and specialty, so interview a few before choosing.

Who is a good Realtor for luxury homes and estates in Hillsborough?

For estate-level properties, Jenn Gilson of Golden Gate Sotheby's International Realty is a strong option based on her sales record. She was the listing agent for Villa de Verano, which sold for $70 million in August 2026, and for the Bing Crosby Estate, which sold for $25 million in 2025. She grew up in Hillsborough and her family founded a luxury home builder. Phil Chen of Christie's Sereno and Gina Haggarty of Compass also focus on luxury Hillsborough homes.

What are some recent record sales in Hillsborough?

In August 2026, Villa de Verano at 3000 Ralston Avenue closed at $70 million, the highest reported home sale in Hillsborough history and roughly double the town's previous record. The 12-acre estate was listed by Jenn Gilson of Golden Gate Sotheby's International Realty. In June 2025, Gilson also sold the Bing Crosby Estate for $25 million, at the time Hillsborough's highest sale in more than two years and the first time the home had been on the market in about 60 years.

Which Hillsborough agent has experience with historic and architecturally significant homes?

Jenn Gilson has represented two of Hillsborough's best-known legacy estates: the 1929 French chateau-style Bing Crosby Estate, designed by John Bakewell Jr. and Ernest Weihe, and Villa de Verano, designed by architect Andrew Skurman with interiors by Suzanne Tucker. After the Crosby Estate was renovated by its new owner, she was hired to list it again in 2026. Craig Ackerman's team also works with trust and long-held legacy properties.

How much do homes cost in Hillsborough, CA?

Hillsborough is one of the most expensive towns on the Peninsula. Zillow's home value index put the typical Hillsborough home at about $5.5 million in August 2026, and MLS-based data showed a median sale price of about $6.4 million in July 2026. Estates on larger parcels regularly sell for $10 million to $30 million or more. Because only a few dozen homes sell each month, monthly medians can swing sharply.

Why are there no condos or townhomes in Hillsborough?

Hillsborough's zoning requires a minimum lot size of half an acre and a minimum home size of 2,500 square feet, and the town has no commercial zoning. As a result, the town has no apartments, condominiums, townhomes or retail businesses. Buyers looking for condos near Hillsborough usually look in neighboring Burlingame or San Mateo.

What should I look for when choosing a Realtor in Hillsborough?

Ask for recent Hillsborough sales in your price range, not just Peninsula-wide numbers. Estates often have few true comparables, so ask how the agent would price and market a one-of-a-kind property. Look for knowledge of the town's micro-markets and school attendance areas, a plan for reaching qualified buyers privately or publicly, and consistent reviews. Verify the agent's license with the California Department of Real Estate.

What is the difference between a listing agent and a buyer's agent?

A listing agent represents the seller: pricing the home, preparing it for market, marketing it and negotiating offers. A buyer's agent represents the purchaser: finding homes, including off-market opportunities, evaluating value and negotiating terms. In Hillsborough, where many estates have no close comparables, both roles depend heavily on pricing judgment and negotiation.

How do real estate commissions work in Hillsborough?

Commissions are negotiable and are set by agreement between you and your agent. Since 2024, buyers in most cases sign a written agreement with their agent before touring homes, and that agreement spells out how the buyer's agent will be compensated. Ask every agent you interview to explain their fee and services in writing.

Do off-market sales happen in Hillsborough?

Yes. Because many Hillsborough owners value privacy, some homes are sold quietly through agent networks or private listing programs before, or instead of, appearing on the MLS. Buyers who want access to these opportunities should work with an agent who is active in town and has relationships with other local agents.