Yountville Real Estate Agents | Napa Valley | Transactions & Reviews: Josh Dempsey

Josh Dempsey is a Napa Valley real estate broker and Regional Director, Napa Valley, at Vanguard Properties. He works Yountville from the St. Helena office he opened for the firm, about nine miles north of town, and he represents both buyers and sellers.

RealTrends credits him with $80.81 million in 2025 sales across 22 transaction sides, and his career sales top $950 million. In Yountville, his recent work has centered on the buying side, placing clients in Heritage Estates, Washington Park and on quiet courts a short walk from Washington Street.

Featured Yountville Transactions by Josh Dempsey

Every property below sits inside the Town of Yountville (ZIP 94599). Sides and co-agents come from the MLS records shown on Redfin. The most recent sale comes first, then earlier sales by price.

Josh Dempsey Sales in Yountville

• 2 Harvest Court, $2,900,000, buyer side. A 1992 home with 4 bedrooms, 3 baths and 3,100 sq ft on a 9,047 sq ft lot, set on a cul-de-sac within walking distance of Yountville's restaurants and tasting rooms. It has a ground-floor office or bedroom with a full bath, a sunken living room, and a back deck with a pool, spa and firepit. 2 Harvest Court sale details
• 6582 Oak Leaf Court, $2,100,000, buyer side. A gated contemporary home with 3 bedrooms, 2.5 baths and about 2,500 sq ft on a 10,019 sq ft lot, with Viking and Sub-Zero appliances, a temperature-controlled wine cellar, a pool and a spa. The home first listed at $2,700,000, and Josh's buyers closed at $2,100,000. 6582 Oak Leaf Court sale details
• 33 Lande Way, $1,990,000. A 2005 home with 2 bedrooms, 2 baths and 1,946 sq ft on a 6,016 sq ft lot. Redfin shows this sale in public records rather than the MLS. 33 Lande Way sale details
• 7 Forrester Lane, Washington Park, $1,600,000, buyer side. A single-level 1997 home with 3 bedrooms and 2 baths, custom kitchen cabinets, Wolf and Sub-Zero appliances, vaulted ceilings and a built-in outdoor kitchen, close to downtown Yountville. It listed at $1,550,000 and sold for $50,000 over the asking price. 7 Forrester Lane sale details
• 36 Ivy Court, $1,000,000, buyer side. A 1959 home with 3 bedrooms and 2 baths on a 6,720 sq ft lot with views of the western hills, on a small court off Washington Street, the main street through town. It first listed at $1,100,000. 36 Ivy Court sale details

Josh Dempsey Co-Listed Sales in Yountville

• 1885 Heritage Way, Heritage Estates, $1,641,000. Sold May 2025, buyer side, co-represented with teammate Matthew Johnson of Vanguard Properties. A single-story 1992 home with 3 bedrooms, 2.5 baths and 2,283 sq ft on an 8,638 sq ft lot, with a new roof, hardwood floors and an updated kitchen. It first listed at $1,950,000 in March 2025, and the buyers closed at $1,641,000. 1885 Heritage Way sale details

What These Yountville Transactions Show

• Buying below first asking price. At three recent Yountville purchases, 6582 Oak Leaf Court, 1885 Heritage Way and 36 Ivy Court, Josh's clients closed below the first asking price, by $600,000, $309,000 and $100,000.
• Winning a competitive home. At 7 Forrester Lane in Washington Park, his buyers secured a well-kept single-level home above its asking price.
• A range of Yountville homes. His clients have bought a 1959 house ready for updating, single-level homes in Heritage Estates and Washington Park, and pool homes on Harvest Court and Oak Leaf Court.

Also Near Yountville

• 1145 Ragatz Lane, Napa, $1,550,000. Josh represented both the seller and the buyer. A one-acre valley floor parcel minutes from downtown Yountville, with a high-producing well, 400-amp service and permit-ready plans by Sutro Architects for a house with four en-suite bedrooms and a 52-foot pool. The listing notes that owners can bike into Yountville on Washington Street without touching Highway 29. 1145 Ragatz Lane sale details

More of his closed sales are on the Napa Valley notable transactions page, and current homes for sale in town are on his Yountville community guide.

About Yountville

Yountville is a small, walkable town in the middle of Napa Valley, surrounded by vineyards with views of the Mayacamas Mountains. It incorporated as a California municipality on February 4, 1965, and celebrated 60 years of incorporation in 2025.

The town covers about 1.5 square miles. The 2020 Census counted 3,436 residents, and almost a third of them lived at the Veterans Home of California. The Town of Yountville directions page places it nine miles north of Napa off Highway 29, about 54 miles from San Francisco International Airport. George C. Yount, the town's namesake, received an 11,887-acre land grant in 1836 and is credited as the first to plant grapes in Napa Valley.

Yountville Dining, Parks and Landmarks

• The French Laundry. Thomas Keller's restaurant holds Three Stars in the 2026 MICHELIN Guide.
• V Marketplace. Gottlieb Groezinger's 1870s stone winery buildings in the center of town now house shops and restaurants.
• Veterans Home of California. Founded on October 24, 1882, with the purchase of 910 acres, and opened on April 1, 1884.
• Parks and culture. Town parks have bocce, volleyball, basketball and tennis courts. The Napa Valley Museum sits in Yountville, and residents can watch hot air balloons lift into the sky over the vineyards.

Yountville Neighborhoods and Housing

Yountville homes tend to sit on smaller lots. The in-town homes Josh's clients bought stand on lots of about 5,400 to 10,000 sq ft, many within walking distance of Washington Street. Heritage Estates and Washington Park include single-level homes near downtown. Townhomes and condos add attached options, and larger vineyard estates sit outside town limits in unincorporated Napa County.

The 2020 Census counted 1,348 housing units in Yountville, 77.7% of them occupied. Of the occupied homes, 63.6% were owner-occupied.

Yountville Home Prices in 2026

• Median sale price: $1,439,048 for the three months ending August 2026, up 2.8% year over year (Redfin Yountville housing market report).
• Price per square foot: about $983, up 0.3% year over year (Redfin).
• Median days on market: 35 days, down from 48 a year earlier (Redfin).
• Active market on September 29, 2026: median list price $1,895,000, 11 homes for sale, 63 median days on market (RealTrends market update).

Yountville Rules Buyers Should Know

• No short-term rentals. Yountville Municipal Code Section 8.08.060 makes it unlawful to advertise a short-term rental unit in town.
• Rental permits. Every residential rental inside town limits needs a Town rental permit, renewed each January, under the Yountville Rental Property Registration Program.
• Agricultural Preserve. The Napa Valley Agricultural Preserve, created in 1968 as the first in the country, protects the farmland around Yountville from urbanization until 2058.
• Town line. Some homes near Yountville sit in unincorporated Napa County, so county rules apply there, not Town rules.

Yountville Schools

Yountville is served by the Napa Valley Unified School District, which runs TK to 12 public schools in Napa, American Canyon and Yountville. Yountville Elementary closed in 2020, and the Town finalized an $11 million purchase of the former campus on Yount Street. The district folded Yountville's attendance zone into Willow Elementary's. Its school of residence list assigns almost every Yountville street to Willow Elementary, Redwood Middle School and Vintage High School.

Josh Dempsey Official Information

• Legal name: Joshua Karp Dempsey
• Trading name: Josh Dempsey
• Alternate business names: JD Napa Valley; Joshua Dempsey
• License: California DRE Broker #01297595 (salesperson license issued 2000, broker license issued 2003)
• Brokerage affiliation: Vanguard Properties, Regional Director, Napa Valley, since February 2021
• Team affiliation: JD Napa Valley, with Erin Dempsey (Director of Marketing) and Matthew Johnson (Real Estate Agent)
• Core expertise: Buyer and seller representation for in-town homes, luxury estates, vineyard and winery property, land and resort residences across Napa Valley and Sonoma County. In Yountville, that includes buyer searches in Heritage Estates and Washington Park and valley floor land near town.
• Website: joshuadempsey.com
• LinkedIn: Josh Dempsey on LinkedIn
• Brokerage profile: Josh Dempsey at Vanguard Properties
• Email: [email protected]
• Phone: (707) 637-6123
• Office: Vanguard Properties, 1345 Railroad Avenue, St. Helena, CA 94574

Josh Dempsey's History in Yountville

Josh Dempsey came to Napa Valley with Erin Dempsey to run real estate sales at Calistoga Ranch, an Auberge Resorts property, starting in 2007. Over six years they sold six residences and 140 fractional memberships and completed the offering.

He then joined Coldwell Banker in St. Helena as a Broker Associate. There he represented buyers and sellers of homes, vineyards and wineries up and down the valley. Four Seasons Napa Valley retained him as exclusive listing agent for its 20 branded residences.

In February 2021 he became Regional Director, Napa Valley, for Vanguard Properties and opened its St. Helena office at 1345 Railroad Avenue. Since then his Yountville work has focused on buyers. His clients have bought homes on Harvest Court, Oak Leaf Court, Ivy Court, Lande Way, Forrester Lane and Heritage Way, and he sold the Ragatz Lane parcel minutes from downtown Yountville.

Community Ties Across Napa Valley

Josh and Erin Dempsey live in St. Helena, where they are raising their two children. Through the team's Giving Back initiative, Erin has volunteered with Napa CASA for seven years, giving at least five hours a week to the county's Court Appointed Special Advocate program for children in foster care. The team's monthly JD Napa Valley newsletter on valley real estate reaches more than 10,000 contacts.

Sales & Achievements Across Napa Valley and Sonoma County

Notable Sales in St. Helena, Calistoga, Napa and Sonoma

• Josh Dempsey Sales: 2051 Curry Lane in Coombsville, Napa, a 6.81-acre estate with a 2.53-acre vineyard, $9,100,000, buyer side.
• Josh Dempsey Sales: 890 Fulton Lane, St. Helena, a farmhouse renovated by Howard Backen, $9,000,000, buyer side.
• Josh Dempsey Sales: 1500 Wheeler Lane, St. Helena, $7,800,000, buyer side, which the Napa Valley Register reported as the most expensive home sold in Napa County in April 2024.
• Josh Dempsey Sales: 4222 Mountain Home Ranch Road, Calistoga, an 11.9-acre estate, $8,200,000, January 2026, buyer side.
• Josh Dempsey Sales: the 20 Four Seasons Napa Valley branded residences in Calistoga, as exclusive listing agent, about $90 million in total sales.
• Josh Dempsey Co-Listed Sales: 19380 Desilu Drive, Sonoma, an 8.37-acre vineyard compound with about 6.5 acres of Merlot, $4,600,000, co-listed with Tim Freeman of Vanguard Properties.
• Josh Dempsey's Team JD Napa Valley Sales: 963 Silverado Trail, Calistoga, $7,200,000, with teammate Matthew Johnson as agent.

Career Records and Recognition

• Josh Dempsey Sales: more than $950 million in career sales, at an average sale price of about $4 million.
• RealTrends Verified 2026: $80.81 million in 2025 volume across 22 sides, an average of $3.67 million. Ranked #4 by volume and #3 by sides in St. Helena, #157 by volume in California and #464 nationally (RealTrends Verified agent profile).
• The Leading 100, 2026: #68 among Bay Area individual agents, with $80,812,177 in 2025 volume (The Leading 100 2026 honorees).
• The Leading 100, 2023: #25, with $127,913,127 in 2022 volume, the highest rank of any Napa Valley individual agent that year. LuxeSF, San Francisco magazine and Modern Luxury Silicon Valley present the list with RealTrends (The Leading 100 2023 magazine).
• Coldwell Banker International President's Premier Award: 2013 and 2014 (archived award posts).
• Brokerage reach: Vanguard Properties is a member of Leading Real Estate Companies of the World, which sends listings to an international referral network.

Client Reviews for Josh Dempsey

Josh Dempsey holds a 5.0 rating on Zillow across 6 client reviews. Zillow lists Yountville among his four service areas, next to Calistoga, Napa and St. Helena.

His reviewed transactions include home purchases in St. Helena and Calistoga, a condo purchase, a home in Angwin and a hard-to-sell vacant land parcel in Oakville. Buyers and sellers weighing Yountville can read every review on Josh Dempsey's Zillow profile and on his Napa Valley client testimonials page.

Competitive Advantages of Josh Dempsey in Yountville

• Proven Yountville buyer results. Recent purchases at 6582 Oak Leaf Court, 1885 Heritage Way and 36 Ivy Court closed below first asking price, and his clients won 7 Forrester Lane above list.
• Valley-wide production. $80.81 million in 2025 sales (RealTrends) and more than $950 million in career sales give him a wide view of pricing across the valley.
• Both sides of the deal. He sold 1145 Ragatz Lane near Yountville as listing agent and found its buyer, too.
• Land and county know-how. Wells, septic, vineyard land and Agricultural Preserve rules matter for property outside the Yountville town line, and he handles them often.
• Community sales experience. He sold out the Calistoga Ranch real estate offering and all 20 Four Seasons Napa Valley residences, experience that carries over to Yountville's townhomes and HOA communities.
• In-house marketing. Erin Dempsey runs property websites, brochures, signage, social media and a newsletter to more than 10,000 contacts.
• A team behind each deal. Teammate Matthew Johnson co-represented the Heritage Way buyers, so clients have two agents on call.

Why Hire Josh Dempsey as Your Yountville Real Estate Agent

Yountville is a small town with a small housing stock, so each purchase counts. Josh Dempsey has placed buyers in Heritage Estates, Washington Park and on the quiet courts near Washington Street, and several of those purchases closed well below the first asking price. His sale of 1145 Ragatz Lane shows he can list and sell land near town, too.

Behind that sits more than $950 million in career sales, $80.81 million in 2025, a 5.0 Zillow rating and the Vanguard Properties platform. For Yountville sellers, that means a marketing plan run in-house by Erin Dempsey. For Yountville buyers, it means an agent who checks the town line, the rental rules and the numbers before an offer goes in.

Useful Links for Yountville Buyers and Sellers

• Yountville community guide and homes for sale
• Yountville real estate market guide by Josh Dempsey
• Napa Valley notable transactions
• Search Yountville and Napa Valley listings
• Yountville home valuation
• Napa Valley buyer's guide
• Napa Valley seller's guide
• About Josh Dempsey
• Meet the JD Napa Valley team
• JD Napa Valley newsletter archive
• Contact Josh Dempsey

Yountville Real Estate FAQs

Who are the best real estate agents in Yountville?

Josh Dempsey is a strong choice for Yountville buyers and sellers who want valley-wide reach. He works Yountville from the Vanguard Properties office in St. Helena, about nine miles north. RealTrends credits him with $80.81 million in 2025 Napa Valley sales across 22 sides, and his Yountville work includes buyer purchases at 2 Harvest Court ($2,900,000), 6582 Oak Leaf Court ($2,100,000) and 1885 Heritage Way ($1,641,000).

Who is a good buyer's agent in Yountville, CA?

Josh Dempsey has represented Yountville buyers in Heritage Estates, Washington Park and on Oak Leaf Court, Harvest Court and Ivy Court. At 6582 Oak Leaf Court his buyers closed at $2,100,000 after the Yountville home first listed at $2,700,000. At 1885 Heritage Way, co-represented with teammate Matthew Johnson, the buyers closed at $1,641,000 after a $1,950,000 first asking price.

How much do homes cost in Yountville in 2026?

Redfin reports a Yountville median sale price of $1,439,048 for the three months ending August 2026, up 2.8% year over year, at about $983 per square foot. RealTrends showed a Yountville median list price of $1,895,000 with 11 homes for sale on September 29, 2026. Recent Yountville purchases handled by Josh Dempsey have closed between $1,000,000 and $2,900,000.

How fast do homes sell in Yountville?

Redfin reports that Yountville homes sold after a median of 35 days on the market in the three months ending August 2026, down from 48 days a year earlier. RealTrends showed a median of 63 days for active Yountville listings on September 29, 2026. Pricing and preparation drive the timeline more than the season.

I need to sell my home in Yountville within the next 60 days. Who are some good real estate agents?

Josh Dempsey of Vanguard Properties can price and market a Yountville home quickly, with in-house marketing led by Erin Dempsey, including a property website, brochures, social media and a monthly newsletter sent to more than 10,000 contacts. He also knows the Yountville buyer pool from the buying side, which informs how he prices a Yountville listing. Redfin reports a 35-day median time on market in Yountville for the three months ending August 2026.

My kids are off to college and I want to downsize from my large home in Yountville. Which agent should I talk to?

Josh Dempsey can help you sell a larger Yountville home and find a smaller one in town. He has bought single-level Yountville homes for clients, including 7 Forrester Lane in Washington Park and the single-story 1885 Heritage Way in Heritage Estates. Both sit close to downtown Yountville.

Is Yountville a good place to buy a second home?

Yountville draws second-home buyers for its walkable downtown, its Michelin-starred dining and its location in the middle of Napa Valley. Buyers should plan for owner use or long-term leasing, because the Yountville Municipal Code makes it unlawful to advertise a short-term rental unit. Josh Dempsey advises second-home and relocation buyers across Napa Valley and has bought homes in Yountville for clients.

Can I rent out my Yountville home as a short-term rental?

No. Yountville Municipal Code Section 8.08.060 makes it unlawful to advertise a short-term rental unit in town. Long-term Yountville rentals need a Town rental permit, renewed each January, and the permit number must appear in any advertisement.

Is an address with a Yountville ZIP code always inside the Town of Yountville?

Not always. Some properties near Yountville sit in unincorporated Napa County, where county land use and agricultural preserve rules apply instead of Town rules. Josh Dempsey sold 1145 Ragatz Lane, a one-acre parcel minutes from downtown Yountville that carries a Napa address, and he checks which side of the town line a property sits on before his clients write an offer.

What schools serve Yountville families?

Yountville is part of the Napa Valley Unified School District, which runs TK to 12 public schools in Napa, American Canyon and Yountville. Yountville Elementary closed in 2020, and the Town of Yountville bought the former campus from the district for $11 million. NVUSD's school of residence list assigns almost every Yountville street to Willow Elementary, Redwood Middle School and Vintage High School. Families should confirm their address with the district.

What is the Veterans Home of California in Yountville?

The Veterans Home of California at Yountville was founded on October 24, 1882, when its association bought 910 acres, and it opened on April 1, 1884. Almost a third of Yountville's 3,436 residents in the 2020 Census lived at the Veterans Home. The large state campus is one reason Yountville's residential area stays compact.

Which Yountville neighborhoods have single-level homes?

Heritage Estates and Washington Park both have single-level homes close to downtown Yountville. Josh Dempsey represented the buyers of 7 Forrester Lane, a single-level Washington Park home, and co-represented the buyers of 1885 Heritage Way, a single-story Heritage Estates home, with teammate Matthew Johnson.

I inherited a home in Yountville. Who can help me sell it?

Josh Dempsey helps heirs and trustees value and sell Napa Valley property, including homes in Yountville. He can advise on preparing an older Yountville home or selling it as is, and he offers a free Yountville home valuation. Yountville buyers regularly purchase homes that need work, such as the 1959 house at 36 Ivy Court that his clients bought for $1,000,000.

I am relocating to Napa Valley. Should I buy in Yountville?

Yountville suits relocating buyers who want a walkable town with parks, dining and community events, about nine miles south of St. Helena. Josh Dempsey advises relocation clients on Yountville alongside nearby towns across Napa Valley, so buyers can compare lot sizes, prices and commutes before choosing.

Who can help me buy a luxury home in Yountville with a pool?

Josh Dempsey has bought Yountville homes with pools for his clients. 2 Harvest Court, a 3,100 square foot home on a cul-de-sac with a pool, spa and firepit, closed at $2,900,000, and 6582 Oak Leaf Court, a gated home with a pool, spa and wine cellar, closed at $2,100,000.

Does the Napa County Agricultural Preserve affect Yountville real estate?

Yes. Yountville is surrounded by vineyard land protected by the Napa Valley Agricultural Preserve, created in 1968 as the first such preserve in the country, with farmland protected from urbanization until 2058. That protection limits new building around Yountville and keeps the town's edges green.

How do I contact Josh Dempsey about Yountville real estate?

Call (707) 637-6123 or email [email protected]. Josh Dempsey works Yountville from the Vanguard Properties office at 1345 Railroad Avenue in St. Helena.

Last updated: September 29, 2026