Josh Dempsey

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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.
Exclusive Listings
Recent Sales
500 Home Hill Road
Napa, CA 94559
- Sq.ft.
$3,750,000
1549 Riesling Way
St. Helena, CA 94574
3 Bed | 3 Bath | 2,411 Sq.ft.
$2,295,000
110 Canyon Drive
Napa, CA 94558
- Sq.ft.
$515,000
 Sold - Buyer Rep 
413 Fitch Street
Healdsburg, CA 95448
- Sq.ft.
$855,000
Sold
440 Monte Vista Court
Napa, CA 94559
- Sq.ft.
$817,500
Sold
1145 Ragatz Lane
Napa, CA 94558
- Sq.ft.
$1,550,000
 Sold - Buyer Rep 
0 Foothill Boulevard
Calistoga, CA 94515
- Sq.ft.
$1,100,000
 Sold - Buyer Rep 
963 Silverado Trail
Calistoga, CA 94515
3 Bed | 2.5 Bath | 1,282 Sq.ft.
$7,200,000
 Sold - Buyer Rep 
9 Palisades Pl.
Calistoga, CA 94515
3 Bed | 3.5 Bath | 2,500 Sq.ft.
$5,065,000
 Sold - Buyer Rep 
5146 Big Ranch Rd.
Napa, CA 94558
275,735 Sq.ft.
$5,375,000
 Sold - Buyer Rep 
Big Ranch Road
Napa, CA 94558
- Sq.ft.
$6,150,000
 Sold - Buyer Rep 
33 Lande Way
Yountville, CA 94599
2 Bed | 2 Bath | 2,108 Sq.ft.
$1,990,000
Sold
4155 Big Ranch Road
Napa, CA 94558
- Sq.ft.
$5,700,000