“Not only was Josh one of the best Realtors we have ever used, but he has become a good friend as well.”
Fred H. - St Helena, CA
meet our team
Watch your Napa Valley dreams become a reality.
Josh Dempsey
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. 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.
Erin Dempsey
Erin was raised in Colorado and attended the University of Kansas, earning a BS in Journalism. Upon graduation, she set her sights on the west coast and moved to San Francisco where she worked in media buying for J. Walter Thompson. Having grown up in the mountains, Erin was drawn to the Lake Tahoe area where she worked as a leasing agent for the Village at Northstar. She went on to become the Marketing Manager for the Hyatt at Northstar, and during that time met her future husband, Josh Dempsey.
In 2007, Josh and Erin moved to the Napa Valley where Erin joined the team at Calistoga Ranch, one of the Valley’s most exclusive resorts, as Director of Marketing. After 6 years at Calistoga Ranch, where Erin managed the PR, print and online advertising, website, client outreach programs, photo and video shoots and direct mail efforts, Erin was hired as the Director of Marketing for the Four Seasons Napa Valley Resort and Residences, where she spent the next 2 years marketing the Residences during their initial launch period.
Erin now spends her time as Marketing Director for JD Napa Valley, focused on making sure each new listing is ready for market with all of the elements needed to sell your property quickly and efficiently. With her extensive knowledge in luxury real estate marketing, Erin is able to add her personal touch to the sales process for your property, including gorgeous custom websites, marketing brochures and signage, social media presence, and inclusion in our monthly newsletter, which goes to over 10,000 recipients that have been carefully cultivated over the past 20 years. With such an extensive background in real estate marketing and over 10 years exclusively marketing high end, luxury real estate projects in the Napa Valley, Erin brings a wealth of knowledge and a unique perspective to JD Napa Valley and a keen eye to marketing initiatives effective in selling your property.
Erin enjoys spending her free time with her and Josh’s 2 children, Quinn, age 9 and Hayden, age 11. She enjoys spending time with friends, long walks outside, cooking, traveling, and taking care of Frankie, their family’s 2 year old French Bulldog and their 7 chickens. Erin also volunteers for Napa CASA, a Voice for Children, which has been a big part of her life for the past 7 years.
Matthew Johnson
Matthew was born and raised in Encinitas, CA, a small beach town located just North of San Diego. Jump forward to 2016, he and his wife set their sights on Napa Valley and made the move. He quickly became part of the community making connections in the wine industry throughout Northern California, working with a high-end brands. With 15+ years of experience working in customer-oriented roles, Matthew is very good at understanding his clients’ needs. His calm, friendly demeanor makes him a joy to work with when going through the home buying and selling process.
Passionate, dedicated, and hardworking, Matthew enjoys the challenges and fulfillment that a career in real estate offers. His number one priority is providing top level service to his clients with a personal touch.
Matthew enjoys spending his free time with his wife Devin and their two dogs, Paisley (Australian Shepherd) and Maverick (German Shepherd). He enjoys the outdoors, weekend trips to Tahoe, golfing and spending time where he grew up in San Diego.