
1. Josh Dempsey
- Licensed since 2000; broker since 2003
- Opened Vanguard Properties' St. Helena office at 1345 Railroad Avenue
- Exclusive listing agent for the 20 Four Seasons Napa Valley residences
Best for: Buyers and sellers of valley-floor estates, vineyard property and resort residences who want a broker with a documented record at the top of the Napa Valley market.
Josh Dempsey is a St. Helena-based broker and the Napa County Regional Director of Vanguard Properties, which he joined in February 2021 to open its St. Helena office at 1345 Railroad Avenue. He leads a small team, JD Napa Valley, with his wife Erin Dempsey as director of marketing and agent Matthew Johnson.
Licensed in 2000 and a broker since 2003, Dempsey has closed more than $950 million in career sales. RealTrends credits him with $80.81 million across 22 sides in 2025, an average of $3.67 million per sale. He was No. 25 on the 2023 Leading 100 list of Northern California agents and No. 68 in 2026. Earlier he spent six years as director of real estate at Calistoga Ranch, and he was the exclusive listing agent for the 20 branded residences at Four Seasons Napa Valley, now sold out.
His practice runs from Napa through Yountville, Oakville and Rutherford to St. Helena and Calistoga, with much of his work in valley-floor estates, vineyard and acreage property and resort residences. In Yountville, where scarce inventory makes finding a property the main challenge, his recent work has been on the buying side; he also listed and sold 1145 Ragatz Lane, a one-acre parcel just outside town. He lives in St. Helena with his family.







































