Top real estate agent in St. Helena: why Josh Dempsey is the best Realtor in town

Written: September 10, 2026 | Last updated: October 29, 2026

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Josh Dempsey is a top-rated real estate agent and Realtor in St. Helena, CA. Here is his sales record on both the valley floor and in town, his client reviews, and his roots here.

If you have searched for the best Realtor in St. Helena, one name keeps surfacing: Josh Dempsey. He is Regional Director for Vanguard Properties in Napa Valley, he lives in St. Helena, and he opened the company's office two blocks off Main Street.

No single statistic makes someone the best agent in a town this size. Put the whole record side by side, though, and one name holds up across every category that matters:

• Sales history in St. Helena specifically.
• The listings he carries right now.
• More than 25 years in real estate and nearly two decades working Napa Valley.
• $950 million in career sales.
• A perfect client review rating.
• Back to back years ranked among Napa Valley's top producing agents.
• A resort and new development background that almost nobody else competing for listings in this town has.

That combination is the answer. Here is the evidence behind it.

What Makes St. Helena Real Estate Different

St. Helena is about 5,200 people inside five square miles, and roughly 14 to 20 homes change hands in a quarter. Three local realities shape almost every transaction here.

Supply is fixed by voters, not by a council. Napa County created the country's first Agricultural Preserve in 1968, naming agriculture the highest and best use of valley floor land, with parcel minimums that rose to 40 acres in 1979 and reach 160 acres on watershed land. Measure J moved rezoning power to the ballot box in 1990, and Measure P renewed those protections through 2058. There is no rezoning to wait out and no council to lobby. Every existing parcel is worth more because of it.

Two local rules catch buyers off guard. New development inside the city has to offset its water demand, usually by retrofitting existing homes with efficient fixtures or paying an in lieu fee. That matters the moment a buyer starts planning a pool, an addition, or a second unit. Short term rental permits are also capped at 25 citywide. As of mid 2026 there were 23 active permits and 62 people on the waiting list, you must own the home three years before applying, and the permit dies when the property sells. Outside city limits, short term rentals are banned outright.

There are two markets inside one ZIP code. The valley floor is the classic Napa estate address: Silverado Trail, Zinfandel Lane, Whitehall Lane, deep loam soils and working vineyards. The hills above town, the Spring Mountain District, are large forested parcels on thin volcanic and sedimentary soils with almost no planted acreage by comparison. They sell to different buyers, price on different logic, and carry very different insurance exposure. FAIR Plan fire coverage in the 94574 ZIP has averaged close to $9,925 a year against a statewide average just over $3,000, and FAIR Plan building coverage caps out at $3 million, which strands a large share of St. Helena's estate inventory. More on the town itself is in his St. Helena community guide. In town is a third world again: west side Craftsman bungalows and Victorians a walk from Main Street, competing for a very small pool of houses in the best public school district in Napa Valley.

What Does a St. Helena Real Estate Specialist Do?

A St. Helena specialist prices a home against the right half of the market, then spots the local rule that is about to become someone's problem. That means wells and septic on rural parcels, vineyard leases and replant timing, Ag Preserve setbacks, and water offset math on an addition. It also means asking early if a buyer's insurance quote on Spring Mountain will survive underwriting. An agent from outside the valley tends to find these issues after a deal is in trouble, not before.

St. Helena Market Numbers

The two big public trackers point in different directions. Redfin shows what sold, and Zillow's index tracks typical home values across the town.

Both readings are accurate. In the three months ending June 2026, sales above $3 million jumped roughly 150 percent against the prior year while the $1 million to $2 million band fell about 31 percent. The typical St. Helena house is not appreciating. The mix of what sells has moved sharply upmarket.

Pricing correctly in that environment takes an agent who works both halves of the market and knows which local rule is about to become someone's problem. Josh does.

Meet Josh Dempsey: Roots in St. Helena

Josh Dempsey is Regional Director for Vanguard Properties in Napa Valley and a licensed California broker with more than 25 years in the business. He lives in St. Helena with his wife Erin, who runs marketing for the team, and the two of them raised their children here.

His St. Helena real estate background runs longer, but the short version is that he came into real estate through the analytical door rather than the sales door. He earned an Economics degree from Santa Clara University in 2000 and started in commercial real estate in Silicon Valley. Two years later he moved into residential development, founding Boulders Realty and serving as Broker of Record for a 160 unit condominium project in Truckee. That early work was about absorption rates, product positioning, and pricing a whole community rather than one house at a time. It still shows in how he prices a listing.

His LinkedIn history adds another community-scale assignment: selling home sites, fractional single-family homes and townhomes at Old Greenwood, a 600-acre Jack Nicklaus signature golf course community in Truckee.

Between 2007 and 2013 he was Director of Real Estate at Calistoga Ranch, the Auberge property up valley, where he and Erin sold six residences and 140 fractional memberships. He then spent years at Coldwell Banker's St. Helena office before Vanguard recruited him in 2021. Across his career he has closed $950 million in sales, including more than $165 million in the most recent two year stretch, at an average sale price above $4 million.

What he does for St. Helena clients is less about volume than about the specific problems this town produces. Wells and septic on the rural parcels. Vineyard leases and replant timing. Ag Preserve setbacks. Water offset math on an addition. Will a buyer's insurance quote on Spring Mountain survive underwriting? He keeps a working bench of inspectors, contractors, well drillers, vineyard managers, and land use consultants in the valley, and he uses it during due diligence rather than after a deal falls apart. His California broker license is public record and carries no disciplinary history, which anyone can check on the state's lookup in about a minute.

The Broker Behind the Vanguard Properties Office in St. Helena

In February 2021 Vanguard Properties appointed Josh Regional Director for Napa Valley and asked him to open the firm's sixteenth Northern California office. He chose St. Helena, and specifically the historic building at 1345 Railroad Avenue, one street back from Main. You can read more about the firm on the Vanguard Properties page.

The Napa Valley Register covered the office at its one year anniversary and described him as a St. Helena resident and regional director. His comment then was straightforward: "We are so very proud to be a part of this town and treasure the historic value of our incredible building."

That detail matters more than it sounds. Most agents competing for luxury listings here work out of Main Street offices belonging to national brands with hundreds of agents. Josh built the local office himself, chose the town for it, and lives eight minutes from it. When a seller calls him about a Madrona Avenue listing, he is not driving up from Napa.

The Track Record of a Top St. Helena Real Estate Agent

Very few agents in St. Helena have closed transactions across both halves of this market. Josh has, repeatedly. Zillow credits him with 55 sales in St. Helena, and the tables below show a selection of them.

On the vineyard and estate side, he sold 890 Fulton Lane for $9,000,000, a 6,798 square foot property renovated by architect Howard Backen and built around a 400 year old oak with vineyards on every side. He closed 1500 Wheeler Lane at $7,800,000, a Wade Design Architects house inside the gates of Raymond Vineyards with vineyard views from every room. He also sold 2175 Palmer Drive for $7,000,000 on one of the town's most sought after private drives, about a mile from the town center, and closed 1330 Whitehall Lane at $5,000,000, a valley floor compound with its own eight tenths of an acre of Sauvignon Blanc.

The in town record runs just as deep, and the hills are part of it too. Detail on each sale is in the tables below.

Josh's St. Helena sales between $1.22 million and $9 million cover the valley floor, the in town streets and Spring Mountain. Two of the eight sales on his notable transactions page are in St. Helena: 890 Fulton Lane and 1500 Wheeler Lane.

Josh Dempsey's Current St. Helena Listings

His current listings in St. Helena cover an orchard ranch and an off-MLS single-level home near Main Street.

Josh Dempsey's Featured Sales in St. Helena

These are featured sales from Josh's public record, not a full list. Sides are shown only where a source states them.

Video: 1597 Arrowhead Drive, St. Helena listing video

Video: 280 Pope Street, St. Helena listing video

Video: 1217 Allyn Avenue, St. Helena listing video

Josh also summed up the July 2025 stretch that included both Pope Street and Allyn Avenue on Instagram: more than $20,000,000 closed in two weeks across four deals.

Recent St. Helena Listings

Josh recently listed 1979 Sulphur Springs Road at $11,995,000 in June 2026. This listing is not counted in the sales figures on this page.

More St. Helena Sales From Josh Dempsey's Portfolio

These sales appear on Josh's own site. The page does not state his role or the date for them.

Josh Dempsey Leases in St. Helena

Josh Dempsey's Take on Selling in St. Helena

Josh writes about his work on Instagram, and a few recent posts show how he thinks about St. Helena property.

Great homes often start as off-market conversations. He found 1979 Sulphur Springs Road as an off-market listing before the house existed. In a February 2024 post he wrote about the moment:

"When I first discovered this off-market listing in St. Helena back in May of 2020, I knew the land, location and views were very special and that we needed to move swiftly."

Josh Dempsey, on Instagram, February 2024

His clients bought the land, spent more than three years designing and building, and the finished home was featured in Architectural Digest. In May 2025 he introduced it on Instagram as a new exclusive off-market listing at $11,995,000, ahead of the June 2026 MLS listing.

Sellers and buyers often return. He had helped the sellers of 1410 Adams Street buy the home 11 years earlier. In an October 2026 post he wrote that "it's already been 11 years" and that he represented both sides as the home went "on to another young family."

A rental can lead to a purchase. In an October 2026 reel about 1651 Spring Mountain Road, Josh described finding longtime friends of an old client "a cute spot on Spring Street in St. Helena" to rent. They then hunted for what he called "a special vintage property within walking distance of Main Street", and found the home he describes as "this landmark home."

"a special vintage property within walking distance of Main Street"

Josh Dempsey, on Instagram, October 2026

Momentum shows up in the numbers. In an August 2025 post he noted that more than $20,000,000 closed in two weeks, and tied it to his newsletter:

"If you get my newsletter, you read my reflection on the current market, which noted a growing sense of momentum in the Napa and Sonoma luxury markets this past month."

Josh Dempsey, on Instagram, August 2025

His LinkedIn career history explains why he sells the way he does. At Boulders Realty in Truckee he ran a Broker Outreach Program across North Tahoe, Truckee, the Bay Area and Sacramento for a condominium development, with the exclusive listing of all the developer inventory. That is the same discipline he applies to a single St. Helena listing: decide who the buyer is, then go find that buyer.

Ways Josh Dempsey Can Sell a St. Helena Home

Talk to Josh Dempsey about selling in St. Helena

Off Market and Coming Soon Opportunities in St. Helena

In a town that closes 14 to 20 residential sales a quarter, listings that never reach the portals are a meaningful share of the market. Owners of trophy vineyard estates frequently do not want their property publicly advertised at all.

Josh has spent more than 20 years building relationships with the valley's brokers, agents, vintners, and property managers, and that network is how quiet listings surface. Buyers working with him hear about St. Helena properties before they are listed, and sometimes about properties that are only for sale to the right buyer. Sellers who want discretion get a way to test the market without a public price reduction on their record.

His Instagram shows the pattern. These St. Helena examples come from his own posts:

Who Are the Best Real Estate Agents in St. Helena?

The table below shows the top 10 St. Helena individual agents by 2025 sales volume on RealTrends Verified 2026. Josh Dempsey is listed first. The RealTrends Rank column shows each agent's position by 2025 volume: Josh is fourth by volume and third by sides.

Source: RealTrends Verified 2026 program (2025 sales data), St. Helena individuals by volume, confirmed November 2, 2026. Rankings are by volume. Josh's RealTrends profile also lists him at No. 157 in California and No. 464 nationally by volume.

Who Josh Dempsey Works With in St. Helena

Josh's St. Helena clients fall into a few groups, and each one shows up in his record.

• Estate and vineyard sellers. He sold 890 Fulton Lane at $9,000,000 and 1500 Wheeler Lane at $7,800,000, and he listed 1979 Sulphur Springs Road at $11,995,000.
• In town buyers and sellers. His 1331 Stockton Street, 1851 Vallejo Street and 905 Charter Oak Avenue sales are all in town.
• Relocating and second home buyers. His business is balanced between second home owners, relocation clients and full time valley residents. A Calistoga Ranch owner couple moving from Virginia describe their search in the reviews below.
• Long-hold land and patient sellers. A vacant land seller describes how he stayed with a slow sale for years.
• Renters who want to buy. The 1651 Spring Mountain Road purchase began with a rental search.
• Families moving up. At 1410 Adams Street he represented both the seller and the buyer.

What St. Helena Clients Say About Their Top Realtor

Josh holds a 5.0 star rating on Zillow, and the reviews on that profile date between 2017 and 2020. You can read more client words on his testimonials page.

A buyer with five states of comparison. djhagensr bought a single family home in St. Helena in 2020 and wrote on Zillow in October 2020: "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 star in all areas - knowledge, expertise, responsiveness and negotiations." That is a buyer with five states of agents to measure against.

A seller who needed patience. Michael K. had a difficult vacant land sale in Oakville that took years to complete. Land in this valley trades slowly, and an agent who tells a seller to wait when waiting is right is worth more here than one who pushes for a fast close.

"Over the years it took to find a buyer, Josh's attention never flagged. He did not push us to sell upon receiving unsatisfying offers nor to drop our asking price - rather he encouraged us to wait for the right buyer which he believed would come along."

Michael K., sold vacant land in Oakville, Zillow, July 2018

A relocating couple. Brenda H. and her husband owned at Calistoga Ranch and were deciding where to land full time. Josh found them at the pool, they talked through their needs, and the next day they were looking at houses. Within a week he showed them the house that became their home.

"He is intuitive, articulate, and really listens."

Brenda H., relocating buyer, Josh Dempsey testimonials page

Two St. Helena buyers. jmiller143, who bought a condo in St. Helena in 2017, wrote on Zillow in November 2017: "Josh was very patient with an extended search for the right property. We never felt pressured to do a deal." Josh P., who bought a single family home in St. Helena in 2017, wrote in June 2017: "Josh is honest, professional, and has a deep understanding of the market here in St. Helena."

Recognition and Credentials of a Top St. Helena Realtor

• RealTrends Verified 2026 (2025 sales data). No. 4 by volume and No. 3 by sides in St. Helena, with $80.81 million across 22 sides. RealTrends builds its rankings from closed MLS data rather than agent self reporting.
• The Real Deal Luxury Dossier, Napa Valley (August 2026). No. 4 among the top five brokers by deal volume, at $81 million, based on RealTrends data. Josh noted on Instagram that this was his second year in a row on that list.
• The Leading 100. No. 68 in 2026, with $80,812,177 in 2025 volume, and No. 25 in 2023, with $127,913,127 in 2022 volume. The 2023 list was presented by LuxeSF in partnership with RealTrends and San Francisco Magazine, so that No. 25 placement is his spot among San Francisco Magazine's Top 100 Real Estate Agents in the Bay Area.
• Top five producing agent in Napa Valley two years in a row. Two consecutive years at that level in a valley this competitive says more than any single year ever could.
• Top Agent in Napa Valley, 2022. Per Realist.

Vanguard Properties is a member of Leading Real Estate Companies of the World, so a St. Helena listing gets distribution through an international referral network rather than a single brokerage's client base.

Resort and Development Experience That Pays Off for St. Helena Sellers

Very few agents in St. Helena have sold new construction at scale, and it changes how a listing gets positioned.

Four Seasons Napa Valley retained Josh as the exclusive listing agent for all 20 of its branded residences up valley from St. Helena, priced from $3.5 million. They are now sold out. Before that he ran real estate at Calistoga Ranch for six years. He has also worked in the marketing and sales of Stanly Ranch, Auberge Resorts Collection, and Montage Healdsburg.

Selling a branded residence means competing against a developer's marketing budget, a resort's brand standards, and buyers comparing your property against every other second home option in the country. That work is closer to product strategy than to listing a house. Sellers of high end St. Helena estates get the benefit: pricing built from absorption data rather than from the last three comps, and marketing aimed at the buyer choosing between Napa Valley and Aspen rather than between two Zinfandel Lane houses.

Community Roots in St. Helena

Josh and Erin have raised two children in the valley, and the family's community work runs through Napa CASA, the Court Appointed Special Advocate program. Erin has been involved for seven years and gives at least five hours a week to it. CASA is the only program in Napa County serving children who have been made dependents of the court for their own safety, and its volunteers are often the one consistent adult in a child's life through the whole time they spend in foster care. Learn more about the family's giving back work.

In September 2026 Josh and Erin also attended the Vida OLE! Dinner and Auction at Quintessa in Rutherford, which celebrated the OLE Health Foundation's 40th anniversary, per his Instagram.

Outside work, Josh snowboards, surfs, and mountain bikes, which is a reasonable description of why a lot of his clients want to live here in the first place.

Why Josh Dempsey Is a Top Realtor in St. Helena, All Factors Considered

Any agent can point to one flattering number. The case for Josh is that he holds up on all of them at once.

Sales record. The St. Helena sales featured on this page range between $1.22 million and $9 million, on the valley floor, in town, and up on Spring Mountain. Very few agents here have closed all three.

Listings. A $1,995,000 olive orchard ranch on the market and an off-MLS single-level home at $3,375,000 (as of October 2026), plus an $11,995,000 Architectural Digest featured property he recently listed in June 2026.

Experience. More than 25 years in real estate, nearly two decades of it in Napa Valley.

Career history. An economics degree, a start in Silicon Valley commercial real estate, and years running sales for resort developments. That background is why his pricing arguments hold up under scrutiny.

Reviews. Clients who compare him against agents in five states, and sellers who describe him staying with a hard listing for years without pushing them into a bad offer.

Review rating. A perfect 5.0 on Zillow.

Career sales. $950 million closed, more than $165 million of it in the last two years, at an average sale price above $4 million.

Repeat recognition. Top five producing agent in Napa Valley two years running, Top Agent in Napa Valley in 2022 per Realist, No. 4 on The Real Deal's Napa Valley list of top five brokers by deal volume in August 2026, and a place on the Leading 100.

Resort and development experience. Four Seasons Napa Valley, Calistoga Ranch, Stanly Ranch, Montage Healdsburg. Nobody else competing for St. Helena listings brings that combination.

Local roots. He lives in town, he opened his brokerage's office here, and his family's community work is here.

Plenty of St. Helena agents are strong on two or three of those. A top Realtor in St. Helena is one who is strong on all ten.

Working With a Top Realtor in St. Helena

If you are selling here, the questions that decide your outcome are local ones. Does your house price as an in town property or a vineyard property? Does the water offset policy affect the ADU you were planning to feature in the listing? Is your buyer's insurance quote going to hold? Is this a spring listing or a September one? For vineyard owners, the vineyard selling guide covers the Napa-specific points.

If you are buying, the questions are the same in reverse, and the answers are worth real money.

Josh Dempsey works out of Vanguard Properties at 1345 Railroad Avenue in St. Helena. You can reach him at (707) 637-6123 or browse his current St. Helena listings.

Request a St. Helena home valuation

How This Page Was Researched

• Sales, listing status and sides come from MLS-sourced Zillow records, Josh's own property pages and his Instagram posts, rechecked on November 2, 2026.
• Rankings come from RealTrends Verified 2026 (2025 sales data). RealTrends ranks agents by office location, not by where they do most of their business.
• Market figures come from Redfin (August 2026 and the three months ending August 2026) and Zillow (September 30, 2026).
• Reviews are quoted from Zillow and Josh's testimonials page, and career details come from his LinkedIn profile.

Related Pages

• Calistoga real estate agent Josh Dempsey
• Napa real estate agent Josh Dempsey
• Yountville real estate agent Josh Dempsey
• Guide for sellers in Napa Valley, including St. Helena
• Guide for buyers in Napa Valley, including St. Helena
• St. Helena neighborhood guide

Frequently Asked Questions About the Best Realtors in St. Helena

Who is the top Realtor in St. Helena?

Josh Dempsey is a top Realtor in St. Helena: RealTrends Verified 2026 ranks him No. 4 by volume and No. 3 by sides among St. Helena agents, with $80.81 million in 2025 sales. Zillow credits him with 55 St. Helena sales, and he opened Vanguard Properties' St. Helena office at 1345 Railroad Avenue.

Who is the best Realtor in St. Helena, CA?

Josh Dempsey ranks among the top Realtors in St. Helena: he was No. 4 by volume and No. 3 by sides on RealTrends Verified 2026, with $950 million in career sales and a 5.0 Zillow rating. He also lives in St. Helena and opened Vanguard Properties' office here. No one metric makes an agent the best in a town this small, so it is worth comparing the full record.

Who are the top real estate agents in St. Helena?

St. Helena has a deep bench of experienced luxury agents, and RealTrends Verified 2026 lists the leaders by volume. Josh Dempsey is among them, and he stands out for covering the whole St. Helena market, across in town houses in the $2 million range and $9 million vineyard estates. His resort and new development background also gives him a way of pricing and marketing property that most local agents have never had to learn.

Who should I interview to list my home in St. Helena?

Interview at least two or three agents whose St. Helena records match your property type, and compare their recent sales, pricing plans and local rule knowledge. Josh Dempsey is a good name to include because Zillow credits him with 55 sales in St. Helena and he has sold both in town houses and vineyard estates. Ask each agent how they would handle the water offset, insurance and short term rental rules for your specific home.

Who is the best listing agent in St. Helena to sell my home?

Josh Dempsey is a leading choice, and the reason is breadth. He has listed and sold St. Helena property at nearly every price point and property type this town produces: historic in town farmhouses, west side family homes, hillside houses on Spring Mountain Road, and valley floor estates with working vineyards. Behind that is an economics degree and years pricing and marketing entire resort developments, including all 20 Four Seasons Napa Valley residences.

How long has Josh Dempsey worked the St. Helena real estate market?

He has been in real estate since 2000 and has worked Napa Valley since 2007, first at Calistoga Ranch and later from Coldwell Banker's St. Helena office. In 2021 he became Regional Director for Vanguard Properties and opened its St. Helena office at 1345 Railroad Avenue. He lives in town.

How many homes has Josh Dempsey sold in St. Helena?

Zillow credits Josh Dempsey with 55 sales in St. Helena on his Vanguard Properties profile, out of 134 total sales. The tables on this page show a selection of those public St. Helena records, with individual prices between $1.22 million and $9 million, not his full history.

What awards and rankings has Josh Dempsey earned in St. Helena?

RealTrends Verified 2026 ranks him No. 4 by volume and No. 3 by sides among St. Helena agents, using 2025 data. The Real Deal's Napa Valley Luxury Dossier placed him No. 4 among the top five brokers by deal volume in August 2026, and he is on the Leading 100 (No. 68 in 2026, No. 25 in 2023). He was also named Top Agent in Napa Valley for 2022 per Realist.

What makes the St. Helena real estate market different from Napa or Yountville?

St. Helena is hemmed in by the Napa County Agricultural Preserve and by voter approved land protections running through 2058, so its supply of homesites is effectively fixed. The city also has its own water offset requirement for new development and a hard cap of 25 short term rental permits. Napa city has a far wider price ladder and more inventory, and Yountville is smaller still and bans short term rentals outright.

Does the best Realtor in St. Helena have access to off market listings?

Yes. A meaningful share of high end St. Helena property trades quietly, and Josh Dempsey's relationships across the valley's brokerages, vineyards and property managers are how those opportunities reach his buyers. His October 2026 off-MLS listing at 1517 Chablis Circle in St. Helena is one example.

Can I sell my St. Helena home off the MLS?

Yes, and Josh Dempsey has done it in St. Helena more than once, including an off-MLS listing at 1517 Chablis Circle at $3,375,000 in October 2026. Sellers who want discretion can test the market without a public price reduction on their record. He can walk you through which route fits your St. Helena property.

What is the median home price in St. Helena right now?

Redfin shows a St. Helena median sale price of $2,138,585 for the three months ending August 2026, up 9.7% year over year. Zillow's home value index for the town was $1,630,683 on September 30, 2026, down 0.5% year over year. The gap exists because Redfin tracks what sold and Zillow tracks typical values, and the mix of St. Helena sales has moved upmarket.

How long does it take to sell a home in St. Helena?

Redfin reports a median of 58 days on market in St. Helena for the three months ending August 2026, with homes selling at 92.5% of list price. Pricing correctly on day one matters in a town where roughly 14 to 20 homes change hands in a quarter. Josh Dempsey prices a St. Helena listing against both halves of the market, in town and on the valley floor.

Should I hire a St. Helena real estate agent who specializes in vineyard property?

If you are buying acreage, yes, and you should also make sure they handle in town property. St. Helena buyers routinely start out looking at a vineyard estate and end up on Madrona Avenue, or the reverse. Josh Dempsey has closed transactions in both categories, including hillside property on Spring Mountain Road and valley floor vineyard estates on Whitehall Lane and Wheeler Lane.

Can I run a short term rental on a home I buy in St. Helena?

Almost certainly not, unless you are patient. The city of St. Helena caps short term rental permits at 25, and as of mid 2026 there were 23 active permits with 62 people on the waiting list. You must have owned the property for three years before applying, the permit does not carry over when a home is sold, and in unincorporated Napa County short term rentals are prohibited entirely.

How does a top St. Helena Realtor handle wildfire insurance on hillside property?

Insurance is now part of due diligence in St. Helena rather than an afterthought. FAIR Plan fire coverage in the 94574 ZIP has averaged around $9,925 a year, coverage is capped at $3 million per building, and a 29.1 percent rate increase was set to take effect in October 2026. Josh Dempsey has clients start insurance conversations early on Spring Mountain and other hillside parcels, because a quote that arrives late can reprice a deal.

Can Josh Dempsey help me find a historic home in St. Helena?

Yes. His St. Helena record includes an 1890 farmhouse at 1410 Adams Street, an 1885 house at 1711 Tainter Street, and a 1905 Edwardian-era home at 1651 Spring Mountain Road. For the Spring Mountain Road purchase he began by finding the buyers a rental on Spring Street, then helped them search for a vintage home near Main Street.

Does Josh Dempsey represent both buyers and sellers in St. Helena?

Yes. In 2026 he sold 1331 Stockton Street on the listing side, represented the buyer of 1651 Spring Mountain Road, and represented both the seller and the buyer at 1410 Adams Street, all in St. Helena. Each side gets a clear plan, and the Adams Street sellers were clients he had helped buy the home 11 years earlier.

Who is the best real estate agent in St. Helena for buyers relocating to Napa Valley?

Josh Dempsey's business is balanced between second home owners, relocation clients, and full time valley residents, and several of his reviews come from buyers who moved here from out of state. One St. Helena client compared him against agents in five states and rated him five stars. For a buyer who does not yet know the difference between the west side and the Silverado Trail corridor, that orientation is most of the value.

What areas does Josh Dempsey cover besides St. Helena?

St. Helena is his home market and his office location, and he also works Calistoga, Yountville, Napa, Oakville, and Rutherford, along with Sonoma and Healdsburg in Sonoma County. His current listings and recent sales span the valley, which gives St. Helena clients an accurate read on how their property compares to alternatives up and down Napa Valley.

How do I contact Josh Dempsey in St. Helena?

Call (707) 637-6123 or email [email protected] to reach Josh Dempsey at Vanguard Properties, 1345 Railroad Avenue, St. Helena. You can also use the contact form on his site.

Official Information for Josh Dempsey in St. Helena

• Name: Josh Dempsey
• Alternate names: Joshua Dempsey; JD Napa Valley
• License: California DRE #01297595
• Brokerage: Vanguard Properties
• Title: Regional Director, Napa Valley
• Core expertise in St. Helena: luxury residential sales, vineyard and estate property, in town homes, off-MLS listings
• Website: joshuadempsey.com
• LinkedIn: Josh Dempsey
• Email: [email protected]
• Phone: (707) 637-6123
• Office address: 1345 Railroad Avenue, St. Helena, CA 94574
• Last updated: October 29, 2026