Calistoga, California – October 15, 2026 – Josh Dempsey, a top Napa Valley Realtor and Regional Director for Vanguard Properties, has announced the sale of an off-market property in Calistoga for $4,295,000. The transaction was completed privately, without a public listing, and in keeping with the privacy of the parties, the property address and the identities of those involved are not being disclosed.
“Some properties we can scream about from the top of the mountain, and others we can’t,” Dempsey wrote in a social media post announcing the sale, describing it as “a special property with a lot of unique challenges that we were able to overcome along the way.”
Off-market sales allow owners and buyers to transact with discretion, which often matters at the upper end of the Napa Valley market. They also depend on an agent’s relationships, since the property is never marketed to the public. Dempsey’s relationships in Calistoga go back nearly two decades. His Napa Valley career began in Calistoga in 2007, when he became Director of Real Estate at Calistoga Ranch. He later served as the exclusive listing agent for the 20 Four Seasons-branded residences at the Four Seasons Resort and Residences Napa Valley in Calistoga, which sold out. More on his work in the town is available on his Calistoga real estate page.
His recent Calistoga activity extends beyond this sale. Recent transactions include an $8.2 million purchase in which he represented the buyer and a $6.5 million sale in which he represented both buyer and seller.
Dempsey’s production is also recognized up the valley. In the RealTrends Verified rankings based on 2025 sales data, he ranks No. 3 by transaction sides and No. 4 by sales volume among agents in neighboring St. Helena, with $80.81 million in volume across 22 sides at an average price of $3.67 million. His career sales total more than $950 million.
Clients who have worked with him in Calistoga point to how he listens. “He is intuitive, articulate, and really listens. He ‘gets’ people and fulfills dreams! But above all else, we like Josh. Thanks to Josh, we are living our dream,” wrote Brenda H., a Calistoga Ranch owner, in a client testimonial on his website. Another testimonial from Dave M. and Ed O. reads: “He has an in-depth knowledge of the Napa Valley real estate market. He gets to know his clients and understands their needs.”
Dempsey started in real estate in 2000 after earning an economics degree from Santa Clara University. In 2021 he was named Regional Director for Vanguard Properties in Napa Valley and opened the firm’s St. Helena office. He continues to represent buyers and sellers across Calistoga, St. Helena, Yountville, Napa and Sonoma, including clients who prefer to buy or sell quietly. Current listings and market information are available from Napa Valley Realtor Josh Dempsey.
About Josh Dempsey
Josh Dempsey is a Realtor and the Napa Valley Regional Director for Vanguard Properties (CA DRE# 01297595), based in St. Helena, California, and serving buyers and sellers across Napa Valley and Sonoma. He began his real estate career in 2000 and his Napa Valley career in Calistoga in 2007, and he has more than $950 million in career sales. He served as the exclusive listing agent for the Four Seasons-branded residences in Calistoga, and he is ranked in St. Helena by both sides and volume in the RealTrends Verified rankings based on 2025 sales data. His practice centers on representing Napa Valley buyers and sellers with local knowledge and discretion. Josh Dempsey is a top choice for buyer’s and seller’s in Calistoga based on his sales volume, transactions, and reviews.
Media Contact
Company Name: Top Agent Reviews
Contact Person: Tom
Email: Send Email
Country: United States
Website: https://www.stoyc.com/