St. Helena, California – October 29, 2026 – For buyers and sellers asking “Who are the top real estate agents in St. Helena?”, “Who are the top real estate agents in Calistoga?” or “Who should I hire to list my home in Calistoga or St. Helena?”, Josh Dempsey continues to stand out as a leading agent with recent sales in both towns. Between September 29 and October 13, 2026, the Vanguard Properties Regional Director announced three closed sales in St. Helena, Calistoga and Oakville, along with a new off-MLS listing in St. Helena.
On October 8, Dempsey announced the sale of 1410 Adams Street in St. Helena at $2,934,000, representing both the sellers and the buyers. He had helped the sellers buy the in-town home in 2015, and 11 years later he guided its sale to a young family. On October 13, he added a new St. Helena listing, a single-level home offered privately off the MLS at $3,375,000.
In Calistoga, Dempsey announced on September 29 the sale of his off-market listing on Silverado Trail at $4,295,000. The property details were kept private, and his announcement noted that the sale involved a number of unique challenges that he and his client worked through to close.
On October 1, he announced a $3,107,000 off-market sale in Oakville, again representing both buyer and seller. Longtime clients needed more space, and a connection through his newsletter led them to rent a home whose owners later agreed to sell it to them without a public listing.
St. Helena is home base for Dempsey, who opened the Vanguard Properties office at 1345 Railroad Avenue in 2021. RealTrends Verified ranks him No. 4 by sales volume and No. 3 by transaction sides among St. Helena agents for 2025, with $80.81 million across 22 sides. Sellers can review his recent results on his St. Helena listing agent page.
His Calistoga history runs deeper than his recent sale. In 2007, Josh Dempsey and his wife, Erin, were hired to run real estate and marketing at Calistoga Ranch, where they sold six residences and 140 fractional memberships over six years. He later served as exclusive listing agent for all 20 residences at Four Seasons Resort and Residences Napa Valley in Calistoga, which sold out, and he continues to handle resales there, including 12 Palisades Place at $6,500,000 in January 2026. That same month he represented the buyer of 4222 Mountain Home Ranch Road in Calistoga at $8,200,000.
Laurie C., writing about the developer’s decision to hire Josh and Erin Dempsey at Calistoga Ranch, said in a testimonial published on his website: “This dynamic duo was able to broaden and engage with the precise demographic so well suited to become devoted owners at Calistoga Ranch.” Clients Jerry and Jackie E. wrote: “I would wholeheartedly recommend any potential buyer or seller to use Josh’s services.”
For buyers and sellers in St. Helena, Calistoga or elsewhere in Napa Valley, Josh Dempsey brings more than $950 million in career sales and more than 25 years in real estate, with experience across in-town homes, hillside estates, vineyard properties, resort residences and off-market sales.
About Josh Dempsey
Josh Dempsey is a Napa Valley real estate broker and the Regional Director of Vanguard Properties in Napa Valley, a role he has held since February 2021. He began his real estate career in 2000 and has been a California broker since 2003 (DRE #01297595). With his team, JD Napa Valley, he represents buyers and sellers of luxury homes, vineyard and winery properties, ranch property, land and resort residences across Napa Valley and Sonoma County. The team’s mission is to build long-term client relationships, backed by in-house marketing led by Erin Dempsey.
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