Josh Dempsey Named a Top St. Helena Agent in RealTrends Verified 2026 Rankings
RealTrends Verified ranks Dempsey No. 4 by sales volume and No. 3 by transaction sides in St. Helena, on $80.81 million across 22 sides in 2025.
ST. HELENA: Josh Dempsey, Regional Director, Napa Valley, for Vanguard Properties, has been named a top St. Helena real estate agent by RealTrends Verified, ranking No. 4 by sales volume and No. 3 by transaction sides 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,
St. Helena is a small town with a small number of sales each year, so every listing and every buyer counts,Josh Dempsey, in the announcement
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.Josh Dempsey, in the announcement
An up-valley record
Dempsey’s 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 has handled resales in that community since, including 12 Palisades Place at $6,500,000 in January 2026.
His 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 announcement says the Napa Valley Register reported as the most expensive home sold in Napa County in April 2024. He represented the buyers in both transactions.
Up-valley property rarely fits a standard pricing model,Josh Dempsey, in the announcement
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.Josh Dempsey, in the announcement
Dempsey began his real estate career in 2000 in commercial brokerage in Palo Alto and has held a California broker license since 2003. He reports 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, and he received the Coldwell Banker International President’s Premier Award in 2013 and 2014.
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