
1. Josh Dempsey
Josh Dempsey is a St. Helena based broker and the Napa County Regional Director for Vanguard Properties, where he opened the firm's St. Helena office and leads the JD Napa Valley team. Licensed since 2000, he spent six years as director of real estate at Calistoga Ranch and later served as the exclusive listing agent for the 20 Four Seasons Napa Valley residences in Calistoga, where he still handles resales. His career sales exceed $950 million, and RealTrends placed his 2025 average sale at $3.67 million. He works with buyers and sellers of luxury homes, vineyard and winery estates, acreage and resort residences across Calistoga, St. Helena, Yountville and Napa.



















