Josh Dempsey Named Top St. Helena Real Estate Agent: No. 4 by Sales Volume and No. 3 by Transaction Sides, RealTrends Verified
St. Helena, California – October 1, 2026 – Josh Dempsey, Regional Director, Napa Valley, for Vanguard Properties, has been named a top St. Helena Realtor by RealTrends Verified, ranking No. 4 by sales volume and No. 3 by transaction sides among real estate agents in St. Helena in its 2026 rankings, which are based on 2025 sales data. RealTrends Verified credits Dempsey with $80.81 million in 2025 sales volume across 22 transaction sides, an average sale price of $3.67 million. The same data places him No. 157 in California and No. 464 in the nation by volume.
RealTrends Verified builds its rankings from closed transaction data and assigns each agent to the city of their office. Dempsey works from the Vanguard Properties office at 1345 Railroad Avenue in St. Helena, where he and his wife, Erin, who directs marketing for their team, JD Napa Valley, raised their two children. His RealTrends Verified awards for the 2025 production year include Top Agent by Volume, City Ranked Agent by Volume and City Ranked Agent by Sides.
“St. Helena is a small town with a small number of sales each year, so every listing and every buyer counts,” said Dempsey. “Ranking in the top four by volume and the top three by sides reflects the trust our sellers and buyers placed in us through 2025, and it is a responsibility we take seriously.”
Dempsey’s St. Helena record includes 890 Fulton Lane, a farmhouse renovated by Howard Backen, at $9,000,000, and 1500 Wheeler Lane at $7,800,000, which the Napa Valley Register reported as the most expensive home sold in Napa County in April 2024. He represented the buyers in both transactions. His seller results, current listings and client reviews are collected on his St. Helena listing agent page.
His work extends up the valley to Calistoga, where his Napa Valley career began in 2007 as Director of Real Estate at Calistoga Ranch. He later served as exclusive listing agent for all 20 Four Seasons Napa Valley residences in Calistoga, which sold out at about $90 million in total, and he has handled resales in that community since, including 12 Palisades Place at $6,500,000 in January 2026. Redfin’s records of Calistoga sales at $3 million and above over the past 24 months show him representing a side in seven of 21. Details are on his Calistoga seller results page.
“Up-valley property rarely fits a standard pricing model,” said Dempsey. “A vineyard parcel with a well and septic system, a resort residence and an in-town home each draw a different buyer. Our job is to know which buyer that is and to price and prepare the home for them before it goes to market.”
Buyers and sellers comparing agents in the area can review public ratings and recent sales in independent guides, including the St. Helena Realtors directory at Best Realtor Directories, Top Agent Today’s review of St. Helena real estate agents and The Daily Douglas guide to choosing a Realtor in Calistoga.
Dempsey began his real estate career in 2000 in commercial brokerage in Palo Alto and has been a California broker since 2003. He has more than $950 million in career sales. The Leading 100, presented with RealTrends, ranked him No. 25 among Bay Area individual agents in 2023 on $127,913,127 in 2022 volume, the highest rank of any Napa Valley individual agent that year. He received the Coldwell Banker International President’s Premier Award in 2013 and 2014. Vanguard Properties is a member of Leading Real Estate Companies of the World, which connects Napa Valley listings to an international referral network.
Dempsey and the JD Napa Valley team continue to represent sellers and buyers across St. Helena, Calistoga, Yountville, Napa and the rest of Napa Valley and Sonoma, from the firm’s St. Helena office.
About JD Napa Valley
JD Napa Valley is the real estate team led by Josh Dempsey, Regional Director, Napa Valley, for Vanguard Properties, with Erin Dempsey as Director of Marketing. Dempsey began his real estate career in 2000 and has held a California broker license since 2003 (DRE #01297595). The team represents sellers and buyers of luxury homes, vineyard and winery estates, land and resort residences across Napa Valley and Sonoma. Its mission is to guide each client through a Napa Valley sale or purchase with pricing grounded in closed local sales and marketing produced in-house.
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