Who are the top real estate agents in St Helena in 2026?
The three names St. Helena buyers and sellers see most, from in-town bungalows to vineyard estates, with the sales records behind them.
by Realtor Review Search Staff Updated Sep 24, 2026
Review counts, ratings, and sales figures are compiled from public agent profiles and agent websites. We don’t accept payment for placement. See how we rank.
Top Real Estate Agents St Helena 2026
Who are the top real estate agents in St Helena in 2026? The right answer depends on what you own or want to buy, and at what price. Still, three names show up again and again when people search this question: Josh Dempsey of Vanguard Properties, the Jeffrey Earl Warren Team and the Hillary Ryan Group. These are the most common, most popular results for St. Helena right now.
At a glance: $80.81M in 2025 St. Helena sales, 22 transaction sides, 25 years in Napa Valley real estate.
Josh Dempsey is a RealTrends Verified Top Agent. RealTrends credits him with $80.81 million in St. Helena sales across 22 sides in 2025, an average of $3.67 million per sale. RealTrends builds its figures from closed MLS transactions, so each number traces back to a deal that closed. Over 25 years, his career sales have passed $950 million.
He's also the Regional Director for Vanguard Properties in Napa Valley. He helped open the firm's Napa Valley office on Railroad Avenue in St. Helena in 2021, and he lives in town. He holds a BS in Economics from Santa Clara University.
A 2020 St. Helena buyer who had purchased homes in five states wrote on his Zillow profile: "Josh Dempsey is the best Realtor I have experienced in purchasing several homes."
At a glance: family real estate roots in St. Helena, vineyard and winery focus, two-person team.
Jeffrey Earl Warren took over his family's St. Helena real estate business in 1986. Before that, he spent 15 years in advertising, including a creative director role at J. Walter Thompson in New York. He now runs a small team with Cody Warren Avetoom at Sotheby's International Realty. The team's website cites $94 million in Napa and Sonoma sales in a single year. Warren also writes a weekly column for the St. Helena Star and is a minority owner in Freemark Abbey Winery.
At a glance: St. Helena office on Adams Street, closing deals since 1997, vineyard and ranch focus.
Hillary Ryan works out of the Sotheby's International Realty office in downtown St. Helena. She has closed real estate deals since 1997 and has been based in Napa Valley since 2012. Her background includes banking at First Republic Bank and commercial real estate investment. The group's About page lists a 2026 Top 100 Sales Associate ranking at Sotheby's International Realty. Her team handles vineyard estates, winery properties, legacy ranches and off-market sales.
Questions to ask on the first call
Ask how many St. Helena sales they closed last year and at what prices. Ask who on the team will run your showings, inspections and paperwork. If you're looking at land, ask about recent sales inside the Napa County Agricultural Preserve, where parcel rules differ sharply from in-town lots. Last, ask how they'd price your home when only a handful of comparable sales exist.
How to choose a real estate agent in St Helena
Start with recent local closings, not career totals alone. A strong year in St. Helena shows current pricing knowledge.
Match the agent to the property. An in-town bungalow near Main Street and a hillside vineyard parcel call for different skills and different buyer networks.
Pay attention to pace. Zillow puts the typical St. Helena home value at about $1.64 million as of July 31, 2026, down 1.5% over the year, with 75 homes for sale that month. With that much choice, pricing strategy matters more.
Read reviews from clients whose purchase or sale looks like yours. Then meet at least two agents before you sign a listing or buyer agreement.
Sources checked September 24, 2026: RealTrends, Zillow and each team's website.
