Leave a Message

Thank you for your message. We will be in touch with you shortly.

Finding Your Perfect Home in Wine Country

Josh Dempsey

CA DRE# 01297595

The Best Journey Takes You Home

Guiding You Through Every Step in St. Helena, Napa, and Sonoma.

main

Meet Josh

CA DRE# 01297595

NAPA VALLEY’S LEADING REAL ESTATE AGENT

With over 20 years of experience in real estate sales, marketing, development and customer service, Josh is consistently recognized as a top performer, closing over $650M in sales to date.

In February 2021, Josh was appointed Regional Director for Vanguard Properties in Napa Valley, Josh worked closely with Vanguard Properties 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. Leading with authenticity, humility and hard work have been integral to his success. 

Featured Properties

Recognized by Our Clients

Laurie C.

Laurie C.

Upon the completion of the final phase of construction at Calistoga Ranch in 2008, Olympus as developer opted to take a less conventional approach to the sale of the truly unique wine country residences. Josh and Erin Dempsey w...
Read More
Brenda H.

Brenda H.

We met Josh through Calistoga Ranch where we are owners, allowing us 6 weeks per year in the Napa Valley. He knew we were considering a move from Virginia and were trying to determine where we should land full-time. We discusse...
Read More
Jerry & Jackie E.

Jerry & Jackie E.

Josh is very professional and competent. He is keenly aware of the product he is selling, as well as the marketplace as a whole. His enthusiasm alone goes a long way in making any deal, and regardless of how things work out, he...
Read More
Dave M. & Ed O.

Dave M. & Ed O.

We loved working with Josh! He has an in-depth knowledge of the Napa Valley real estate market. He gets to know his clients and understands their needs. His top priority is making sure that his clients are satisfied. He is resp...
Read More
Alan & Brenda K.

Alan & Brenda K.

It is with great pleasure that we would like to share our positive experience working with Josh Dempsey as our real estate agent. He has a wealth of knowledge and contacts, which he brought to our purchases to make them seamles...
Read More
Fred H.

Fred H.

Not only was Josh one of the best Realtors we have ever used, but he has become a good friend as well! His perception of our needs and tastes was dead-on. Combined with his knowledge of the market and his network, we were looki...
Read More
Buyer

Buyer

Josh Dempsey is the best Realtor I have experienced in purchasing several homes in California, Pennsylvania, Illinois, Massachusetts, and North Carolina. I rate him five stars in all areas - knowledge, expertise, responsiveness...
Read More
Buyer

Buyer

Josh was great from start to finish! We would wholeheartedly recommend him to others seeking real estate in Napa Valley. (Josh assisted us in buying a timeshare at Calistoga Ranch.)
Read More
Michael K.

Michael K.

Ours was a difficult vacant land sale in west Napa County and it took a long time to complete. Over the years it took to find a buyer, Josh's attention never flagged. He did not push us to sell upon receiving unsatisfying offer...
Read More
Drew B.

Drew B.

Josh was a true professional throughout our house hunt in Napa. Not being from this area Josh was really good at letting us know the pros and cons of each area and home. Can’t say enough positive about Josh and our experience w...
Read More
  1. 1
  2. 2
  3. 3

What’s Your Property Worth?

CONTACT INFORMATION

Almost There! You’re 1 Step Away

THANK YOU

Inbox.

Selling A Home?

Explore Our Seller's Guide.

Buying A Home?

Explore Our Buyer's Guide.

Work With Us

We believe real estate is about more than just transactions—it’s about relationships. Whether you’re buying your dream home, selling a cherished property, or investing in Napa Valley, our team is here to provide expert guidance and personalized service. Let’s work together to achieve your real estate goals.

Follow Us on Instagram