Josh Dempsey

In February 2021, Josh became the Regional Director, Napa Valley for Vanguard Properties in Saint Helena. Josh worked closely with Vanguard ownership to open the company’s 15th office in Northern California, and first office in Napa Valley – providing the region with a boutique, luxury real estate service. Equipped with his extensive experience in real estate sales and marketing, Josh has been able to further grow Vanguard Properties’ reach in Northern California to another highly desirable landscape, the Napa Valley. In 2021 Josh closed $120MM in sales, bringing his career production to date to over $550MM.


Raised in Connecticut, Josh ventured west to the Silicon Valley after high school to attend Santa Clara University. Armed with a BS in Economics, and a keen interest in real estate, Josh launched his career in commercial real estate brokerage in Palo Alto in 2000. After two years in the brokerage business, a client hired him to help develop, build and sell 160 condominiums at The Boulders in Truckee, California. At The Boulders, Josh further 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, and in 2008 they were hired as Director of Real Estate and Marketing Director, respectively. Six years later, with 140 fractional memberships and six residences sold, the real estate offering at Calistoga Ranch was complete, and Josh began applying his experience accrued over 13 years as Broker Associate at Coldwell Banker.

After 7 years at Coldwell Banker and over 20 years of experience in real estate sales, marketing, development and customer service, Josh was consistently recognized as a top performer. In addition to representing clients on in-town and country estate properties, Josh was retained by Four Seasons Napa Valley as the exclusive listing agent to sell all 20 Four Seasons branded residences. Sales were brisk and the project was sold at record pricing with $90MM in sales.

One of Josh’s passions is meeting new people. Inquisitive by nature, his demeanor is both analytical and approachable which, along with a strong work ethic, enables Josh to strike the perfect match between the clients and their dream properties. Josh has a deep love for Napa Valley, not just as a tourist destination, but as a warm, inclusive place to raise a family. Erin and Josh now have two young children, and are permanently settled in St. Helena where they are raising their family. When Josh isn’t working or being a Dad, you might find him on a surfboard, a snowboard, or a bike.

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