In my video, I laid out why very rich people are moving to Southern Oregon and why this region is quietly becoming one of the West Coast’s most desirable luxury hideaways. As someone who’s lived here for over 30 years and worked with hundreds of buyers and sellers, I want to give you the full picture in writing: the neighborhoods, the lifestyle, the financial advantages, and the practical steps to find these hidden-off-market treasures. If you’ve been wondering why very rich people are moving to Southern Oregon, read on — I’ll walk you through everything you need to know.

Table of Contents

• Why Very Rich People Are Moving to Southern Oregon
• Ashland Hills and Belle Fiore Estate & Winery
• East Medford Foothills — Modern Luxury on the Ridge
• Jacksonville Vineyards and the Applegate Valley
• Riverfront Properties — the Crown Jewels
• Why the Wealthy Are Choosing Southern Oregon
• What the Southern Oregon Lifestyle Really Looks Like
• How to Access Hidden Luxury Listings in Southern Oregon
• FAQs on Why Very Rich People Are Moving to Southern Oregon
• Conclusion and Next Steps

Why Very Rich People Are Moving to Southern Oregon

There’s a quiet migration happening in 2025: high net worth buyers are seeking out quieter, more value-oriented places with great weather, excellent amenities, and absolute privacy. That desire has put a spotlight on Southern Oregon. If you’re asking “why very rich people are moving to Southern Oregon,” the answer blends lifestyle, economics, and access: beautiful topography (vineyards, rivers, ridgelines), a long recreational season, surprisingly sophisticated cultural offerings, and financial benefits that make luxury holdings stretch much further than they would in places like Napa or coastal California.

This region fits a specific profile: buyers who value peace, privacy, and long-term value over public displays of wealth. That’s a key reason why many of these homes never appear on Zillow — owners and brokers maintain selective, off-market transactions to protect privacy. As a local real estate advisor, I’ve helped many high net worth individuals discreetly find properties that match these tastes.

Ashland Hills and Belle Fiore Estate & Winery

Let’s start with one of my personal favorites: the Ashland Hills. I filmed part of the video at Belle Fiore Estate & Winery just east of Ashland because it’s a perfect example of the combination of scenery, craftsmanship, and local culture that attracts wealthy buyers. Belle Fiore has won awards for its pinot noir, merlot, and cabernet sauvignon, and the estate itself is precisely the type of property that appeals to someone searching for a luxury escape with vineyard potential.

Ashland has a remarkable draw: the town itself is consistently ranked as one of America’s top small arts towns. That proximity to high-quality dining, theater (the Oregon Shakespeare Festival), galleries, and a walkable downtown district makes luxury estates in the hills particularly attractive. A view of Lithia Park and downtown from a private estate, combined with several acres of land and classic mountain vistas, equals a lifestyle that’s hard to beat.

• Why buyers gravitate here: proximity to culture + privacy
• Typical property features: custom estates, vineyards, guest houses, private tasting rooms
• Market characteristic: many of these are privately held or sold off-market

East Medford Foothills — Modern Luxury on the Ridge

The East Medford Foothills offer a different flavor of prestige: contemporary, high-end construction perched on ridgelines with sprawling views of the Rogue Valley. Streets like Aerial Heights, Autumn Hills, and Saddle Ridge have some of the most spectacular builds in the area. These are the neighborhoods where you’ll find newer, custom-built homes with finishes, garages for car collections, and landscaping designed for entertaining.

These properties tend to appeal to buyers who want practical access to Medford — schools, healthcare, and a regional airport — while still enjoying the privacy and elevation that makes a home feel like a retreat. Some homes in this submarket enter the multi-million-dollar range, and a few approach what might be thought of as eight-figure scale for the region.

• Practical benefits: short drive to healthcare, schools, and services
• Common features: open floor plans, luxury kitchens, home theaters, estate-scale garages
• Buyer profile: tech exiles, established business owners, professionals seeking second-home luxury

Jacksonville Vineyards and the Applegate Valley

If the foothills and Ashland Hills are about views and town proximity, the Applegate Valley is about quiet luxury, agricultural potential, and absolute privacy. Jacksonville and the Applegate Valley are dotted with boutique wineries, gated estates, and properties with acreage. The Applegate River winds through the valley floor, producing gorgeous riverfront parcels and providing a recreational backbone to the area.

Properties here invite you to create meaningful hobbies or businesses: boutique wine production, equestrian facilities, or specialty agriculture. You’ll find homeowners who produce private-label wine or who hire producers to manage a small boutique winery on their land. For many buyers who ponder “why very rich people are moving to Southern Oregon,” the opportunity to own a workable estate with revenue potential is a major draw.

• Features: gated entries, vineyards, agricultural buildings, river access
• Privacy level: typically higher than Ashland hills and Medford foothills
• Ideal for: those wanting a hobby vineyard, large acreage, or a secluded compound

Riverfront Properties — the Crown Jewels

Riverfront estates might be the single most romantic reason why very rich people are moving to Southern Oregon. Waterfront properties along the Rogue River, Applegate River, and other waterways are a totally different lifestyle: you can fly fish, kayak, and host friends who float by on rafters. These homes offer a relaxed, slower pace, and they’re often treated as generational holdings.

Pricing here varies: you’ll find million-dollar retreats alongside rare parcels that approach the high single-digit millions for truly exceptional estates. The immersive soundscape of flowing water, mature trees, and the ability to step from your lawn into a kayak are hard to replicate anywhere else in this price range on the West Coast.

• Typical price range: $1M — $10M+ depending on acreage and improvements
• Lifestyle: fly fishing, kayaking, private river access
• Why they matter: unmatched combination of privacy, recreation, and natural beauty

Why the Wealthy Are Choosing Southern Oregon

There are several specific reasons many affluent buyers are choosing Southern Oregon right now. These aren’t just feel-good arguments — they’re practical financial and lifestyle decisions that add up.

1. Privacy and a low-key culture

One of the most cited reasons is simply: peace and no paparazzi. Many high-profile figures have found refuge here because communities are respectful of privacy, and the culture favors understated wealth. Celebrities like Patrick Duffy and Jim Belushi have owned riverfront estates here; historically, figures like John Wayne and Bing Crosby have also retreated to the area. This discretion is a commodity in itself.

2. Financial value compared to California

A home priced at $2–3 million in Southern Oregon can represent the same lifestyle and utility as a $20+ million home in California’s most expensive markets. You get more land, more space, and more privacy for the money — and that stretches your investment while reducing carrying costs.

3. No state sales tax and favorable property tax structure

Oregon has no state sales tax, which matters for everyday cost-of-living as well as large purchases. Property taxes in Oregon are generally lower than in California, and importantly, Oregon does not reassess property value at sale in the same way some other states do. Property taxes are based on assessed value, and there are protections that can keep taxes comparatively affordable over time.

4. Insurance costs and lower operating expenses

Homeowners insurance is traditionally lower across much of Oregon compared to other coastal states. Lower insurance and lower taxes compound over time and make owning large estates more sustainable.

5. Accessibility — Rogue Valley International Airport

Southern Oregon’s Rogue Valley International Airport makes this region surprisingly accessible. Direct service to places like San Francisco, Los Angeles, Seattle, Portland, Denver, Salt Lake City, Phoenix, and Las Vegas means you can own a secluded estate without sacrificing travel convenience. That combination of privacy plus good flight options is a huge draw for buyers maintaining business and family ties elsewhere.

What the Southern Oregon Lifestyle Really Looks Like

Let’s be frank: Southern Oregon is not about ostentatious displays. It’s about experience. The lifestyle here is “serenity over status.” Quiet trails, fly fishing early in the morning, private vineyard dinners, and art-filled weekends in Ashland—these are the moments luxury buyers are paying for.

If you want private chefs, top-tier contractors, luxury remodels, or exclusive vineyard services, you can have them. Local vendors have grown to support high-end clients in a discreet fashion: private chefs who rotate menus for gatherings, vineyard managers who run small-batch production under a private label, and contractors who specialize in elegant yet understated estate work.

How to Access Hidden Luxury Listings in Southern Oregon

Here’s a critical reality: many of Southern Oregon’s most desirable properties never hit the public market. Owners selling to protect privacy often prefer off-market transactions. That means the difference between finding a dream estate and never knowing it existed is having the right local relationships.

To effectively pursue these listings, you’ll want an agent who:

• Lives and breathes the local luxury market
• Has trusted relationships with other local brokers and owners
• Understands discreet, confidential transactions
• Can advise on running a vineyard, protecting an estate, or converting property into a revenue-generating boutique winery

That’s the kind of experience I bring to the table. I’ve worked with numerous high net worth individuals and families who needed privacy, discretion, and local knowledge to secure the right property without public marketing.

FAQs on Why Very Rich People Are Moving to Southern Oregon

What kind of properties can I expect if I’m searching for luxury in Southern Oregon?

Expect variety: estate vineyards with tasting rooms, riverfront parcels with private banks, ridge-top custom homes with panoramic views, equestrian ranches, and gated compounds in the Applegate Valley. Prices vary by location and improvements, ranging from modest million-dollar retreats to multi-million-dollar generational estates.

Why aren’t many luxury properties listed on Zillow or other public sites?

Privacy is the primary reason. Many owners wish to avoid public attention, and off-market sales allow selective exposure to qualified buyers only. Additionally, some sellers prefer direct negotiations and relationship-based deals to maintain confidentiality.

Is Southern Oregon practical for frequent travelers?

Absolutely. Rogue Valley International Airport has direct flights to major cities across the West and Mountain regions. The travel infrastructure supports both remote lifestyles and frequent commuting to business centers or family hubs.

What are the tax benefits of relocating to Oregon?

Oregon has no state sales tax, and property taxes are typically lower than in California. Property tax assessment rules in Oregon also create greater predictability for long-term owners. That said, always consult a tax professional for individual advice, as personal circumstances vary.

Can I run a small winery or private-label wine operation on my property?

Yes. Many buyers purchase properties with vineyard potential or existing vines. You can run an estate winery yourself, hire a winemaker, or contract production to local boutique producers. It’s a unique opportunity to offset hobby costs and potentially create revenue while enjoying the lifestyle.

What amenities and services support the luxury market here?

Southern Oregon offers top-tier contractors, private chefs, vineyard management services, luxury interior designers, and specialty landscapers. The Ashland cultural scene provides dining and entertainment, and Medford’s healthcare and services support an affluent lifestyle without the travel burdens of remote rural areas.

Conclusion and Next Steps

If you’re trying to understand why very rich people are moving to Southern Oregon, the answer comes down to a mix of privacy, value, climate, culture, and convenience. Buyers are choosing the region because they can have a larger, more private, and more versatile estate for significantly less capital than coastal luxury markets. Add a low-key culture, excellent year-round recreation, an accessible regional airport, and the ability to privately produce wine or enjoy riverfront life, and you have a compelling proposition.

For anyone seriously considering this lifestyle, the critical step is partnering with an advisor who knows where the off-market opportunities lie. If you want help finding quiet luxury — estates, vineyards, or riverfront homes that may never appear on public sites — reach out to us at 541-827-8767 , your local specialist who can open those doors.

My goal has always been to help discerning buyers find the right property, whether it’s a second home that becomes primary, a generational estate, or a boutique agricultural property. If the idea of discovering why very rich people are moving to Southern Oregon resonates with you, I’d welcome the opportunity to guide your search!