Josh Dempsey
In February 2021, Josh became the Managing Broker of Vanguard Properties in Saint Helena. Josh is working closely with Vanguard leadership 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 will be able to further grow Vanguard Properties’ reach in Northern California to another highly desirable landscape.
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, closing over $400MM in sales to date. 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 the completion and closing of all 20 residences ($90MM in sales) scheduled to close in 2021.
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.
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, closing over $400MM in sales to date. 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 the completion and closing of all 20 residences ($90MM in sales) scheduled to close in 2021.
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.
Contact Josh
Lic. # 01297595
Languages Spoken
English
Recent Sales
Sold - Buyer Rep
2 Spyglass Court
Napa, CA 94558
Napa, CA 94558
3 Bed | 3 Bath | 3,265 Sq.ft.
$2,000,000
Sold - Buyer Rep
7 Forrester Lane
Yountville, CA 94599
Yountville, CA 94599
3 Bed | 2 Bath | 1,224 Sq.ft.
$1,600,000
Sold
44 Burning Tree Court
Napa, CA 94558
Napa, CA 94558
3 Bed | 4 Bath | 2,968 Sq.ft.
$2,775,000
Sold
18775 Deer Park Drive
Sonoma, CA 95476
Sonoma, CA 95476
4 Bed | 5 Bath | 5,275 Sq.ft.
$4,175,000
Sold
19380 Desilu Drive
Sonoma, CA 95476
Sonoma, CA 95476
3 Bed | 3 Bath | 2,825 Sq.ft.
$4,600,000
Sold - Buyer Rep
963 Silverado Trail
Calistoga, CA 94515
Calistoga, CA 94515
3 Bed | 2.5 Bath | 1,282 Sq.ft.
$7,200,000
Sold
280 Pope St
St. Helena, CA 94574
St. Helena, CA 94574
5 Bed | 5 Bath | 4,018 Sq.ft.
$4,677,000
Sold
1330 Whitehall Lane
St. Helena, CA 94574
St. Helena, CA 94574
4 Bed | 6 Bath | 4,309 Sq.ft.
$5,000,000
Sold - Buyer Rep
9 Palisades Pl.
Calistoga, CA 94515
Calistoga, CA 94515
3 Bed | 3.5 Bath | 2,500 Sq.ft.
$5,065,000
Sold
300 Alta Loma Drive
Angwin, CA 94508
Angwin, CA 94508
3 Bed | 4 Bath | 2,507 Sq.ft.
$1,590,000
Sold - Buyer Rep
5146 Big Ranch Rd.
Napa, CA 94558
Napa, CA 94558
275,735 Sq.ft.
$5,375,000
Sold - Buyer Rep
Big Ranch Road
Napa, CA 94558
Napa, CA 94558
- Sq.ft.
$6,150,000
Sold - Buyer Rep
934 Signorelli Circle
St. Helena, CA 94574
St. Helena, CA 94574
3 Bed | 3 Bath | 1,542 Sq.ft.
$1,650,000
Sold - Buyer Rep
33 Lande Way
Yountville, CA 94599
Yountville, CA 94599
2 Bed | 2 Bath | 2,108 Sq.ft.
$1,990,000
Sold
4155 Big Ranch Road
Napa, CA 94558
Napa, CA 94558
- Sq.ft.
$5,700,000
Sold
3761 Silverado Trail
Calistoga, CA 94515
Calistoga, CA 94515
4 Bed | 4 Bath | 3,823 Sq.ft.
$5,250,000
Sold
2880 Foothill Boulevard
Calistoga, CA 94515
Calistoga, CA 94515
4 Bed | 5 Bath | 3,641 Sq.ft.
$3,995,000
Sold - Buyer Rep
1407 Maxwell Avenue
Napa, CA 94559
Napa, CA 94559
2 Bed | 2 Bath | 1,400 Sq.ft.
$900,000