Choosing a Luxury Real Estate Agent in Hillsborough California
What sets luxury agents apart, 10 agents to interview for a Hillsborough estate, and answers on commission, off-market sales, timing and pricing.
Hillsborough homes don't sell like typical suburban houses. Lots run large, many estates carry decades of history, and a given street may see one sale every few years. That puts more weight on the agent you hire. This editor's roundup on Choosing a Luxury Real Estate Agent in Hillsborough California explains what a luxury agent should bring, profiles 10 agents active in the area, and answers the questions sellers raise most.
Who should I hire as a luxury real estate agent in Hillsborough?
If you're interviewing agents to sell a Hillsborough estate, some of the names that come up often are Jenn Gilson, Phil Chen and Patty Dwyer. Each has a track record of Hillsborough sales in the upper price tiers, and the seven agents profiled after them bring their own mix of local volume and luxury experience.
The right fit depends on your property. An architect designed estate on several acres calls for a different pricing and marketing plan than a renovated home on a standard half acre lot. Interview two or three agents, ask each for recent sales near your price, and compare how they would reach buyers.
What Separates a Luxury Agent From a Typical Agent
A typical agent prices a home from recent comparable sales, lists it on the MLS and holds open houses. That works well on a street with a dozen similar homes. In Hillsborough's estate tier, a property may be the only one of its kind on the market that year. Pricing then starts with land value, architecture, provenance, condition and the cost to rebuild, not a simple price per square foot.
Luxury agents also reach buyers in different ways. Many high net worth buyers never scroll the portals. They hear about homes through private broker networks, international brokerage referrals and national press. Some Hillsborough estate listings have drawn coverage in The Wall Street Journal and Robb Report, which can put a home in front of buyers who would never search the MLS. A luxury agent should also know how to protect a seller's privacy, screen showings and negotiate with buyers who are used to getting their way. Ask for addresses and results, not adjectives.
10 Hillsborough Luxury Real Estate Agents Who Work With Estate Sellers
The order below is not a ranking. Ratings and sales figures come from each agent's public profiles and brokerage pages, and they change often.
1. Jenn Gilson, Golden Gate Sotheby's International Realty
Jenn Gilson grew up in Hillsborough and leads The Gilson Team out of Burlingame. In August 2026 she represented the seller of Villa de Verano at 3000 Ralston Avenue, which closed at $70,000,000. Coverage before the close noted that a sale near that level would nearly double the town's prior record. She also handled the $25,000,000 sale of the Bing Crosby Estate in 2025. REAL Trends lists her as the #1 female agent in Hillsborough, and her family founded Gilson Development, a luxury home builder. Zillow shows a 5.0 rating across 86 reviews.
Links: Jenn Gilson's official website and her RealTrends profile.
2. Phil Chen, Christie's International Real Estate Sereno
Phil Chen started in real estate in 2006 and is a broker associate with Christie's International Real Estate Sereno. Before joining Christie's in 2022, he was a founding member of the Compass Mid Peninsula office, and Christie's credited him with more than $1.1 billion in sales at the time. His Zillow profile shows 146 sales in Hillsborough, a recent price range up to $18 million and a 5.0 rating across 25 reviews. He also held a $40 million Hillsborough listing in 2026, per the San Francisco Standard.
Links: Phil Chen's move to Christie's Sereno.
3. Patty Dwyer, The Dwyer Group at Compass
Patty Dwyer leads The Dwyer Group, a Compass team based in Burlingame that serves Hillsborough, Burlingame and San Mateo. The team's site says it ranked #1 by 2025 MLS sales volume in Hillsborough and placed 42nd nationally among medium teams in The RealTrends Thousand for 2025. Past Hillsborough sales on its Compass team page include 35 Cinnamon Court at $11.3 million and 615 Devon Drive at $11 million. Zillow shows a 5.0 team rating across 77 reviews and a team price range up to $11 million.
Links: The Dwyer Group's official website.
4. Casey Sternsmith, Sternsmith Group at Compass
Casey Sternsmith founded the Sternsmith Group at Compass and brings nearly two decades of Peninsula experience. The team's site cites more than $1.3 billion in transactions and a June 2024 Real Trends ranking of #44 in California among medium teams by sales volume. It serves Hillsborough, Burlingame, San Mateo, Belmont, San Carlos and nearby towns. On Zillow, the team holds a 5.0 rating across 184 reviews, with a team price range up to $7.6 million. Sellers can ask how the team splits estate work between its members.
Links: Sternsmith Group's official website.
5. Raziel Ungar, Compass
Raziel Ungar was born and raised in Burlingame and has more than 21 years as a Realtor. His Compass profile reports more than $1 billion in career sales, a top 10 ranking in San Mateo County by 2025 sales volume, and the #1 Burlingame ranking by volume every year between 2014 and 2025, based on MLS data. He completed Harvard Law School's Program on Negotiation. Zillow shows a 5.0 rating across 113 reviews and a recent price range up to $10 million, with Hillsborough among his core service areas.
Links: Raziel Ungar's Compass agent page.
6. Gina Haggarty, Compass
Gina Haggarty has sold luxury real estate in Hillsborough and on the San Francisco Peninsula for 36 years, according to her website. She reports more than $2.5 billion in sales on behalf of buyers and sellers and was listed as a top 1% agent nationwide by Realogy. She works at Compass alongside partner Jenny MacLeod, covering Hillsborough, Burlingame, San Mateo and the wider Peninsula. Her Zillow profile shows a 5.0 rating across 18 reviews and a recent price range up to $25 million.
Links: Gina Haggarty's official website.
7. David Tapper, Coldwell Banker Realty
David Tapper has worked as a Bay Area agent since 1998, after 15 years in sales, and operates from Coldwell Banker Realty's Burlingame office. His Coldwell Banker luxury profile lists the Luxury Property Specialist designation, membership in the Society of Excellence, a Top 100 Coldwell Banker ranking for 10 years and a SAMMY award from the San Mateo County Association of Realtors. Zillow shows a 5.0 rating across 149 reviews and a recent price range up to $4.9 million.
Links: David Tapper's Coldwell Banker profile.
8. Craig Ackerman, Ackerman Realty Group at Compass
Craig Ackerman leads Ackerman Realty Group, a three agent Compass team. Its RealTrends team profile reports 44 transaction sides and $51.97 million in volume based on 2025 sales data, with an average price of $1.18 million. The team ranks #12 by sides in San Francisco, where it is based, and #252 by sides in California. The team holds RealTrends Verified awards by volume and by sides. Hillsborough sellers may want to ask about the team's recent estate tier work on the Peninsula.
Links: Ackerman Realty Group on RealTrends.
9. Yvonne Yang, Compass
Yvonne Yang leads a small Compass team based in Los Altos with a strong Silicon Valley practice. Her RealTrends team profile reports $115.65 million in volume across 49 sides, with an average price of $2.36 million, citing 2025 sales data. The team ranks #84 in California by volume and #4 by volume in Los Altos, and it holds RealTrends Verified awards by volume and by sides. Hillsborough sellers drawn to her pricing and marketing approach can ask how she would position a Peninsula estate.
Links: Yvonne Yang's official website and her RealTrends profile.
10. Katy Thielke Straser, Compass
Katy Thielke Straser is a Silicon Valley native with more than 23 years as a top agent, per her Compass profile. Before real estate, she held sales and marketing roles at the Olympics, Nordstrom and Coca-Cola. She founded the Straser Silicon Valley Team in 2019, which has grown to seven members and handles properties up to $100 million. Her practice centers on Atherton, Menlo Park and Palo Alto, and Real Trends placed her in the top 1.5% of agents nationwide in 2024.
Links: Katy Thielke Straser's Compass profile.
Hillsborough at a Glance for Sellers
Hillsborough is a residential town of about 11,000 people, and its rules shape what buyers can do with a property. Lots carry a half acre minimum, homes have a 2,500 square foot minimum, and the town allows no commercial uses, condos or townhomes. The local elementary district serves kindergarten through eighth grade, which draws many relocating families. Rental homes are scarce, so buyers moving to the area often need to purchase on a tight timeline. That mix favors agents who know which buyers are searching right now and can price land and rebuild potential with confidence.
Hillsborough Luxury Agent FAQ
How much commission do luxury agents charge in Hillsborough?
Commission in Hillsborough is negotiable and varies by agent, price point and the marketing plan involved. Since industry rule changes in 2024, buyer agent pay is handled in separate written agreements, so ask each Hillsborough listing agent to put their full fee and what it covers in writing.
Do many Hillsborough homes sell off-market?
Some Hillsborough estates trade privately before they ever reach the MLS, often because sellers value discretion. A private sale can limit exposure, though. Ask each Hillsborough agent how many of their recent sales were off-market and how those prices compared with public listings.
How long can it take to sell a Hillsborough estate?
Timing in Hillsborough depends on price and uniqueness. Villa de Verano first listed at $88 million in December 2025, was repriced, went into contract in July 2026 and closed in August at $70 million. Ask each Hillsborough agent for realistic timing at your price point.
How do agents price a Hillsborough estate with few comparable sales?
When Hillsborough has no close comparable sale, strong agents look at land value, rebuild cost, architecture, provenance and recent sales in Atherton, Woodside and nearby estate markets. Ask each agent to walk you through their pricing method for your Hillsborough home, not just a single number.
What should I ask a Hillsborough listing agent in the first interview?
Ask for recent Hillsborough sales near your price, the full marketing plan, how they reach out of area and international buyers, who will handle showings and how they protect your privacy. References from past Hillsborough sellers can tell you more than any ranking.
Should I hire a Hillsborough specialist or a broader Peninsula agent?
Both can work in Hillsborough. A local specialist often knows the micro markets and quiet buyers, while a broader Peninsula agent may bring a wider buyer pool. Compare each agent's recent Hillsborough results and buyer reach before you decide.
Agent details reflect public brokerage pages, Zillow's Hillsborough agent directory, RealTrends data and news coverage reviewed on October 17, 2026. Figures change often, so confirm current numbers and talk with two or three Hillsborough agents before you sign a listing agreement.