St. Helena Realtors

Josh Dempsey

• 20+ years in Napa Valley real estate, marketing & development
• $870M+ in career sales, $165M+ in the past two years
• Named a Top 100 Bay Area agent by San Francisco Magazine
• Opened Vanguard Properties' St. Helena office in 2021

Josh Dempsey works out of St. Helena, where he opened Vanguard Properties' office on Railroad Avenue in 2021, the brokerage's 16th Northern California location, and now serves as the company's Regional Director for Napa Valley. He has spent more than 20 years in real estate sales, marketing and development, with career production of more than $870 million and over $165 million closed in the past two years alone.

His background runs deeper than typical residential sales. Before Napa Valley, he worked in Silicon Valley commercial real estate and founded a residential development firm in Truckee, then served as Director of Real Estate at Calistoga Ranch and exclusive listing agent for the Four Seasons Resort and Residences Napa Valley. That history shows up in how he handles the transactions that trip up generalist agents here: wells, septic systems, vineyard and winery estates, land use questions, insurance and new development.

San Francisco Magazine named him one of the Bay Area's Top 100 real estate agents, and Realist has ranked him among Napa Valley's top five producing agents two years running and the top agent in the county in 2022. He is a REAL Trends Verified agent, a past International President's Premier award winner, and a member of Leading Real Estate Companies of the World. Outside the office, he and his wife Erin, who leads the team's marketing, have raised their two children in the Valley they work in.