Josh
Dempsey

Napa County
Regional Director

Share/Save
Back to Management
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 2021 and 2022 he closed over $220MM in sales, bringing his career production to date to over $650MM.

After graduating Santa Clara University with a BS in Economics, Josh launched his career in commercial real estate brokerage in Palo Alto in 2000. After two years in the brokerage business, a developer 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 2007 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 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.

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 clients and their dream properties. Erin and Josh now have two school-aged children and are 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.