Calistoga, California – November 15, 2026 – For homeowners searching “Who are the top real estate agents in Calistoga?” or “Who should I hire to sell my home in Calistoga?”, Josh Dempsey of Vanguard Properties is a top option. Dempsey, a top-producing Napa Valley Realtor with a specialty in Calistoga luxury real estate, currently has three active listings for sale in Calistoga, with a fourth Calistoga listing pending.
Key Takeaways
Josh Dempsey has three active listings in Calistoga, priced from $1,000,000 to $6,900,000, and a fourth Calistoga listing that is pending.
The Real Deal named him No. 4 among the top five brokers in Napa County in August 2026, with $81 million in deal volume, based on RealTrends data.
He was the exclusive listing agent for all 20 private residences at Four Seasons Napa Valley in Calistoga and earlier served as Director of Real Estate at Calistoga Ranch.
His published sales portfolio shows 21 sales in Calistoga, 20 of them at $1 million or more.
Three Active Calistoga Listings
The three active listings cover two homes and one parcel of land. 21 Lawley Lane is a four-bedroom, five-bath home of 3,370 square feet offered at $6,900,000. 1015 Bale Lane is a three-bedroom, two-bath home of 1,907 square feet offered at $2,400,000. 4500 Silverado Trail is a 4.8-acre parcel offered at $1,000,000. All three are listed through Vanguard Properties, where Dempsey is the Regional Director for Napa Valley.
A Long History in Calistoga
Dempsey’s work in Calistoga goes back to Calistoga Ranch, where he served as Director of Real Estate and where six residences and 140 fractional memberships were sold. He was later retained by Four Seasons Napa Valley as the exclusive listing agent for all 20 of its private residences. The residences, located at the resort in Calistoga, have since sold out.
His published sales portfolio shows 21 sales in Calistoga, 20 of them at $1 million or more. They include 4222 Mountain Home Ranch Road at $8,200,000 and 3533 State Highway 128 at $7,017,677, two purchases in which he represented the buyer. His practice covers luxury estates, vineyards, wineries, ranch and country property, land and in-town homes, including transactions that involve wells, septic systems and land use.
A client review on Zillow, from buyers he assisted at Calistoga Ranch, reads: “Josh was great from start to finish! We would wholeheartedly recommend him to others seeking real estate in Napa Valley.”
Achievements
In a Napa Valley feature published August 2, 2026, The Real Deal listed Dempsey fourth among the top five brokers in Napa County, with $81 million in deal volume, citing RealTrends data. Dempsey shared the recognition on Instagram, where he noted it was his second year in a row among the top five.
RealTrends Verified credits him with $80.81 million in sales volume across 22 transaction sides, based on 2025 sales data. RealTrends lists him under St. Helena, where his office is located, and ranks him No. 4 in that city and No. 157 in California by volume.
He is No. 68 on the 2026 Leading 100 list of Bay Area agents, presented by LuxeSF in partnership with RealTrends and San Francisco Magazine. Dempsey has closed $950 million in career sales, including more than $165 million over the past two years.
Dempsey represents sellers and buyers in Calistoga, St. Helena, Yountville and Napa. His office is at 1345 Railroad Avenue in St. Helena.
About Josh Dempsey
Josh Dempsey is a Realtor and the Regional Director for Vanguard Properties in Napa Valley, based in St. Helena, California. Licensed in California since 2000, he established and opened the firm’s St. Helena office in February 2021. He represents buyers and sellers of luxury estates, vineyards, wineries, land and in-town homes in Calistoga, St. Helena, Yountville and Napa. His stated approach is to tailor the level of service to each client and to stay responsive and hands-on through closing.
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