Napa County
Regional Director

Back to Management
In Napa Valley, Josh Dempsey’s name is synonymous with luxury real estate sales. In February 2021, Josh was appointed Regional Director for Vanguard Properties in Napa Valley. Josh worked closely with Vanguard ownership to open the company’s 16th office in Northern California located in the heart of St Helena. Over the past decade, Josh has consistently ranked among the top producers in wine country and in 2022 he closed over $110,000,000 in sales, bringing his career production to date to over $650,000,000.

Josh began his career in real estate immediately after graduating from Santa Clara University with a BS in Economics in 2000. After two years in the commercial real estate brokerage in Silicon Valley, a local developer client hired him to help develop, build and sell 160 condominiums at The Boulders in Truckee, California. At The Boulders, Josh honed his knowledge of construction, marketing and sales, and ultimately founded Boulders Realty to act as Broker of Record for the project. During this period, Josh met his future life partner, Erin, and they married in 2007. With Josh’s background in real estate and Erin’s in marketing, they formed a strong team that appealed to the owners of Calistoga Ranch, a luxury resort and residences project by Auberge Resorts, and in 2007 they were hired as Director of Real Estate and Marketing Director, respectively. Six years later, with six residences and 140 fractional memberships sold, the real estate offering at Calistoga Ranch was complete, and Josh began applying his experience as Broker Associate at Coldwell Banker in St Helena. In addition to representing clients on residential, vineyard and winery properties, Josh was retained by Four Seasons Napa Valley as the exclusive listing agent to sell the Four Seasons branded residences. Sales were brisk and the project was sold at record pricing. Josh continues to work as a broker in Napa Valley and is recognized as a market leader, representing both buyers and sellers of some of the most spectacular properties on the market. Josh focuses on fostering long-term relationships with his clients and fellow brokers. Leading with authenticity, humility and hard work have been integral to his success.