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About Hillary Ryan

Napa Valley’s Top Luxury Real Estate Agent

Hillary Ryan is one of Napa Valley’s highest-producing luxury real estate agents, with over $1 billion in closed sales volume across Napa Valley and Sonoma Wine Country. Ranked among the Top 100 Sales Associates at Sotheby’s International Realty and recognized as a Top Producer by RealTrends / LuxeSF Bay Area, Hillary leads the Hillary Ryan Group at Sotheby’s International Realty’s St. Helena office — one of the most active and trusted teams for high-value wine country transactions.

With nearly 30 years of real estate experience dating to 1997, Hillary brings an institutional-caliber foundation to every transaction. Her career spans banking (First Republic Bank), commercial real estate investment (Prado Group, AMB Property Corporation/Prologis, DivcoWest), and residential brokerage — giving her clients a strategic advantage in complex, high-stakes negotiations.

Credentials & Recognition

Top 100

Sales Associate — Sotheby’s International Realty (Annual Ranking)

Top Producer

RealTrends Verified — Bay Area LuxeSF designation

$1B+

Closed Sales Volume — Napa Valley & Wine Country

30 Years

Nearly Decades of Active Transactional Experience (since 1997)

B.S. Economics

UC Berkeley

Licensed

CA DRE# 01934302

2024 & 2025

Affiliated with Sotheby’s International Realty, the #1 Most Represented Luxury Brand in Real Trends Verified + the Thousand Rankings

Top 250

RealTrends, 2019–2025

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Market Expertise

Napa Valley Luxury Real Estate

Hillary Ryan Group specializes in Napa Valley’s most coveted communities — Napa (94558 & 94559), St. Helena, Rutherford, Yountville, Oakville, Calistoga, and Sonoma — representing the full spectrum of wine country property:

  • Vineyard Estates & Winery Properties

  • Luxury Residential ($3m–$20m+)

  • Legacy Ranches & Agricultural Land

  • Development & Investment Acquisitions

Off-Market & Private Transactions

Current Market Context (2025): Napa County’s median home price crossed $1,025,000 in Q2 2025, up 5.1% year-over-year, with luxury properties in St. Helena and Rutherford commanding significant premiums. Price per square foot reached over $2000/SF, and properties in the $5M+ segment remain highly competitive. Hillary Ryan Group operates at the top of this market, with active listings priced from $4.35M to $19.95M.

Why Clients Choose Hillary Ryan Group

Hillary applies market analytics, land use expertise, and risk assessment to every engagement — evaluating properties through both a financial and design lens. Her deep understanding of what drives value in Wine Country — provenance, architectural quality, terroir, lifestyle positioning — enables her clients to buy and sell with clarity and confidence.

Her professional network includes attorneys, architects, contractors, and global Sotheby’s colleagues, providing off-market access and cross-border buyer reach across Silicon Valley, San Francisco, and international feeder markets.

Contact Hillary Ryan Group

Sotheby’s International Realty — St. Helena
1229 Adams St, St. Helena, CA 94574

Hillary Ryan

Hillary Ryan

Top 100 Sales Associate at Sotheby’s International Realty
Leading 100 Top Producer in Bay Area LuxeSF, RealTrends

Hillary Ryan is one of Napa Valley's most established and consistently top-producing luxury real estate advisors. In 2026, she was recognized among the Top 100 Sales Associates worldwide at Sotheby's International Realty, reflecting nearly three decades of advising buyers and sellers of significant real estate. Since making Napa Valley her home in 2012, Hillary has closed more than $1 billion in Napa Valley and Sonoma transactions while drawing on a career that has encompassed more than $7 billion in commercial and residential real estate. She represents founders, technology executives, investors, family offices, entrepreneurs, and multigenerational families acquiring and selling some of Wine Country's most exceptional properties. Prior to residential brokerage, Hillary held positions with First Republic Bank, Prado Group, AMB Property Corporation (now Prologis), and DivcoWest. This institutional background shaped the analytical approach, financial sophistication, negotiation skills, and disciplined thinking she brings to every transaction.

Hillary is known for helping clients see beyond architecture and aesthetics. She evaluates each property through the lens of long-term value, privacy, infrastructure, land-use potential, agricultural capability, operational considerations, and future resale positioning. Her deep understanding of Napa County regulations, entitlement processes, and development opportunities enables clients to make informed decisions and avoid costly surprises. Her longstanding relationships with property owners, brokers, attorneys, architects, planners, engineers, vineyard professionals, and contractors provide access to exceptional opportunities, many of which never reach the public market. Clients value her discretion, responsiveness, direct communication, and ability to simplify complex decisions while protecting their interests.

For sellers, Hillary develops highly tailored marketing strategies that position each property to achieve its greatest potential. She combines sophisticated market analysis, compelling storytelling, and targeted exposure to qualified buyers throughout Napa Valley, San Francisco, Silicon Valley, Southern California, and international markets. She understands how to communicate not only a property's beauty, but also its provenance, privacy, architectural significance, agricultural attributes, development potential, and long-term investment value.

Whether representing a buyer searching for an extraordinary Napa Valley property or a seller entrusted with marketing a significant estate, Hillary Ryan is known for providing insightful advice, exceptional service, complete discretion, and an experience defined by professionalism, trust, and lasting relationships.

A longtime Northern California resident, Hillary has lived in San Francisco, Marin County, and Napa Valley. She attended The Hamlin School in San Francisco and Justin-Siena High School in Napa before earning a Bachelor of Science in Economics from the University of California, Berkeley. Hillary lives in Napa Valley with her husband and their indulged dachshund. Hillary has an intimate understanding of what makes life in Napa Valley distinctive and values her role in creating a dynamic community. Hillary currently serves on the Board of Olé Health Foundation. Hillary appreciates thoughtful architecture, indoor-outdoor living, wellness, exceptional food and wine, and a genuine connection to the land. Outside of work, she enjoys traveling to visit her college-aged sons, exploring local restaurants and music venues, practicing yoga, and hiking the trails of the valley she is proud to call home.

What Clients Say

"Hillary Ryan's integrity was evident throughout our search for a Napa Valley home. Her honesty, judgment, and market knowledge instilled confidence. Due to Hillary’s local network of property owners and brokers, we purchased an exceptional off-market property we never would have known existed. We now have an incredible home that we enjoy sharing with our friends and family." – AJR

"Hillary Ryan and her team are extraordinarily knowledgeable, professional, and thoughtful. They are hard-working and make themselves available when we needed them. Alexa and Hillary clearly explained the strengths, limitations, and potential for the homes we considered. Hillary's expertise gave us complete confidence throughout the process, and we are grateful for her guidance in helping us purchase our ideal Napa Valley home." – SCZ

Alexa Weber

Alexa Weber

Alexa Weber leads marketing strategy for the Hillary Ryan Group at Sotheby’s International Realty, specializing in positioning distinctive properties throughout Napa Valley and Wine Country. As Director of Strategic Marketing & Due Diligence, she oversees how the team’s listings are branded, marketed, and discovered by qualified buyers locally and globally. Weber has worked alongside Hillary Ryan since 2019, helping shape the team’s marketing strategy, brand presence, and client experience.

Her work sits at the intersection of data, design, and storytelling. Weber combines market analytics, advanced digital advertising, and creative direction to craft compelling narratives that elevate homes beyond traditional listings. From vineyard estates and legacy ranches to architecturally significant properties, she focuses on highlighting the provenance, design pedigree, and lifestyle experiences that resonate with today’s luxury buyer. She also collaborates with the global PR team at Sotheby’s International Realty to position notable properties for potential coverage in leading media outlets worldwide.

In addition to marketing strategy, Weber leads due diligence preparation for the team’s listings, coordinating inspections and working closely with contractors, inspectors, and other specialists to evaluate property condition and documentation prior to bringing homes to market. She manages disclosure preparation and has a strong working knowledge of California disclosure requirements, helping ensure properties are thoughtfully prepared and presented with clarity and transparency.

Prior to joining the Hillary Ryan Group, Weber served as Regional Marketing Advisor for Compass (formerly Pacific Union International) across Napa and Sonoma counties, where she advised more than 150 real estate professionals on marketing strategy and digital advertising. During Compass’s rapid growth as a venture-backed technology startup, she helped agents adopt newly introduced AI-powered marketing tools and platforms. In that role, she developed and managed targeted campaigns across Google Display Network, Google Keyword Search Ads, YouTube Ads, and Meta’s Facebook and Instagram ecosystems, building expertise in audience targeting, campaign analytics, and digital brand positioning.

Today, Weber applies that expertise to create integrated marketing strategies for luxury properties, combining photography, video, social media storytelling, targeted digital campaigns, and emerging technologies to connect exceptional homes with discerning buyers across key feeder markets including Silicon Valley and the San Francisco Bay Area.

Alexa studied photography at Sonoma State University and remains actively engaged in the Napa Valley community. She supports organizations including Young Professionals of Napa Valley and Jameson Humane, where she has adopted two adult cats and given them a beautiful second chance at life. Outside of real estate, Alexa enjoys Napa Valley’s healthy outdoor lifestyle: visiting the farmers market, attending local music and wellness events, enjoying the many available hiking trails, exploring the newest restaurants, and supporting the valley’s thriving small business community.

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Refined Representation for Discerning Clients

Hillary Ryan brings clarity, sophistication, and unmatched professionalism to Northern California’s most sought-after real estate opportunities.

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