Overpriced towns to avoid in Southern Oregon — if you're moving, retiring, or investing in Southern Oregon, this is the honest breakdown you need. I'm Brian Simmons with the Buying Southern Oregon Real Estate Team, and over the years my team and I have helped hundreds of families relocate, retire, and invest confidently across the region. In this guide I’ll walk you through why some of the most popular towns can be overrated or overpriced, what trade-offs you’ll face, and solid, nearby alternatives where your dollar will stretch further.

Throughout this post I’ll cover East Medford (Town #1), Ashland (Town #2), Jacksonville (Town #3), some practical alternatives (Town #4), and Rogue River (Town #5). I’ll give median price data, lifestyle notes, and clear pros and cons so you can make a smarter decision. If you want the video or a downloadable relocation guide, you’ll find ways to reach out at the end — but first, let’s dive in.

Note: If you’re searching online, remember the phrase  overpriced towns to avoid in Southern Oregon — it summarizes this post and will help you find the core comparison points as you plan your move.

Table of Contents

• Overpriced Town #1 - Medford (East Medford)
• Overpriced Town #2 - Ashland
• Overpriced Town #3 - Jacksonville
• Overpriced Town #4 - Alternatives (Runners Up & Value Picks)
• Overpriced Town #5 - Rogue River (More Detail)
• How to Use This Information (Practical Steps)
• Relocation Resources & Next Steps
• FAQs About the Overpriced Towns to Avoid in Southern Oregon
• Final Thoughts

Overpriced Town #1 - Medford (East Medford)

East Medford is one of the most sought-after parts of the region, and for very good reasons: proximity to the hospital, medical specialists, jobs, amenities, golf courses like Centennial, and a lot of newer, higher-end development. When people say they “live in East Medford,” there’s a certain status associated with that—it's the higher-end section of Medford.

But popularity comes with a price. The median sales price in East Medford is currently about $515,000, compared with the broader Southern Oregon median of roughly $450,000. That difference reflects demand more than anything else: centrally located, highly walkable neighborhoods, and abundant amenities.

Here’s what to expect if you target East Medford:

• Pros: Central location, excellent access to healthcare and jobs, walkability, parks, and higher-end homes.
• Cons: Higher median price, more density, less privacy, and a market with stronger competition.

If you love the Medford vibe but want more value for your money, consider nearby alternatives that give you similar benefits without the premium price tag.

VIEW HOMES IN MEDFORD SOUTHERN OREGON

Alternative: Twin Creeks, Central Point

One of my favorite recommendations to clients who initially target East Medford is the Twin Creeks neighborhood in Central Point. Twin Creeks ticks many of the same boxes: very central, minutes from Medford (roughly 10–15 minutes to the hospital, under 10 to the airport), walkable neighborhoods with parks and paths, and a wide variety of homes.

What you’ll find in Twin Creeks:

• Home choices from older 2000s era homes in the $400k range to brand-new builds near the $750k range.
• A median sales price around $480,000, noticeably less than East Medford’s $515k.
• Good value if you want centrality and walkability without paying the East Medford premium.

Yes, Twin Creeks shares some of the same suburban trade-offs — density and limited privacy compared to rural areas — but for many buyers the cost savings and equivalent lifestyle are well worth it. If your target is East Medford because of convenience, give Twin Creeks a hard look.

Overpriced towns to avoid in Southern Oregon can be a useful mindset when you’re comparing neighborhoods—don’t automatically assume the most popular or prestigious area is the smartest purchase.

VIEW HOMES IN TWIN CREEKS SOUTHERN OREGON

Overpriced Town #2 - Ashland

Ashland is the cultural heartbeat of Southern Oregon. Between the Oregon Shakespeare Festival, Southern Oregon University, beautiful Lithia Park, mountain biking, and nearby skiing, Ashland has an undeniable and lasting appeal. That cultural cachet and its unique vibe make it a top choice for many buyers—but it’s also one of the most expensive markets around.

The current median sale price in Ashland is about $580,000, which places it among the highest-priced towns in Southern Oregon.

Here’s what to keep in mind about Ashland:

• Pros: Rich cultural life, boutique shopping, restaurants, parks, walkable downtown, and close access to outdoor recreation.
• Cons: Higher price point, culturally distinct (college town vibe), and somewhat isolated from the rest of Southern Oregon in terms of lifestyle and politics.

Ashland’s identity as a college town and arts hub means it’s an outlier — in a good way — but that also makes it expensive and sometimes less accessible to buyers on a budget.

VIEW HOMES FOR SALE IN ASHLAND SOUTHERN OREGON

Alternative: Talent

If you love Ashland but can’t justify the price, check out Talent. It’s just outside Ashland (usually a short 5–10 minute drive), and offers many of the lifestyle benefits — restaurants, community feel, and proximity to the theater and parklands — at a lower median price of around  $450,000.

Highlights of Talent:

• Lower median price than Ashland while remaining very close to Ashland’s amenities.
• Up-and-coming feel after rebuilding efforts following the Almeda Fire (2020/2021), with thoughtful development and new community spaces.
• Less of a downtown vibe than Ashland, but a solid value play if you want accessibility to Ashland without the premium.

Choosing Talent over Ashland is a strategic decision that gives you access to Ashland’s lifestyle with significantly less money tied up in housing.

Overpriced towns to avoid in Southern Oregon often means asking: “Do I want the name and downtown vibe, or do I want the lifestyle?” Talent answers the latter without the Ashland price tag.

Overpriced Town #3 - Jacksonville

Jacksonville is famous for its historic charm. Founded in the mid-1800s, it has a preserved downtown with beautiful old buildings and a small-town feel that attracts retirees and buyers looking for a serene, picturesque community.

Median price in Jacksonville is currently around $650,000, making it one of the priciest towns in the region — often topping the list alongside Ashland.

VIEW HOMES FOR SALE IN JACKSONVILLE SOUTHERN OREGON

When clients target Jacksonville, they usually want:

• Historic charm and walkable downtown life.
• A quieter, more mature community with a strong retiree presence.
• Proximity to Medford for services while maintaining a distinct small-town identity.

Drawbacks include the high median price and a demographic tilt toward retirees, which can influence the town’s energy. If you’re raising young kids and want a more active, kid-friendly community with louder suburban life, Jacksonville may feel less suited.

Alternative: Grants Pass (G Street)

Grants Pass, especially the G Street area, offers many of the same historic downtown features as Jacksonville but at a significantly lower price point — median home prices in Grants Pass are typically under  $450,000.

What Grants Pass gives you:

• A vibrant, walkable downtown with excellent restaurants (Twisted Cork, Laughing Clam, Bohemian, Lulu’s, and more).
• Historic architecture and a small-city feel without the “retiree-only” reputation.
• A broader range of housing options, from historic in-town homes to riverfront properties and rural acreage.

Grants Pass is larger than Jacksonville, offering more variety for different buyer types and budgets. If you want historic charm and a livelier downtown while keeping costs down, Grants Pass is a compelling alternative.

Overpriced towns to avoid in Southern Oregon doesn't mean you skip charm—it means you shop smarter and compare nearby communities that deliver the same lifestyle at better value.

VIEW HOMES FOR SALE IN GRANTS PASS SOUTHERN OREGON

Overpriced Town #4 - Alternatives (Runners Up & Value Picks)

Outside the high-profile towns, there are several fantastic communities that often get overlooked but offer great value, convenience, and a strong quality of life.

Eagle Point

Median price: about  $489,000.

Why Eagle Point? It’s a small town with a golf-course-centered lifestyle, a friendly downtown, and lots of new development. Many buyers willing to live 20 minutes outside Medford find Eagle Point offers big lifestyle wins for the price.

• Appeals to families and retirees who want a small-town feel with newer construction options.
• Golf course, parks, and a pleasant downtown stretch that’s walkable and community oriented.

VIEW HOMES FOR SALE IN EAGLE POINT SOUTHERN OREGON

Shady Cove

Median price: around  $410,000.

Shady Cove offers a similar small-town vibe and excellent river access, but it can be more touristy and busier during summer months. It’s another worthwhile alternative depending on how much seasonal traffic you’re comfortable with.

Across these alternatives you’ll find more bang for your buck — new construction, larger lots, quieter streets, and a slower pace of life without sacrificing access to services in Medford or Grants Pass.

Overpriced towns to avoid in Southern Oregon by widening your search radius — the right town might be just a 15–30-minute drive away and give you a much better return on investment.

Overpriced Town #5 - Rogue River (More Detail)

Let’s dig a bit deeper into Rogue River since it’s both a practical option and my personal home base. At a median price of roughly $500,000, Rogue River sits at a comfortable midpoint: more affordable than Jacksonville and Ashland, but offering convenient access to the larger hubs.

Key lifestyle features:

• Everything you need locally: grocery, pharmacy, hardware, restaurants, gas, banking, and medical services.
• Close enough to Grants Pass (10 minutes) and Medford (20 minutes) when you need big-city amenities.
• River access, community events, and a classic small-town atmosphere that still attracts families and retirees alike.

Rogue River is a strong example of an option that gives you lifestyle quality without overpaying for “status.” In many cases I’ve seen clients choose Rogue River for daily life and still enjoy quick access to higher-end dining and entertainment when they want it.

If you’re serious about avoiding overpriced towns, consider what you use daily versus what you visit occasionally. Often the town you visit for dinner, or a show doesn’t have to be the town you call home.

How to Use This Information (Practical Steps)

Here’s a practical approach you can use right now to avoid overpaying and find the right fit:

1. Define your must-haves: commute time, school districts, yard size, single-story vs. multi-level, and proximity to healthcare.
2. Identify the “must-visit” towns — then pick 2–3 nearby alternatives that match the lifestyle but have lower median prices.
3. Compare total cost of ownership: property taxes, insurance (including wildfire considerations and flood zones), HOA fees, and commute costs.
4. Visit on different days and at different times: busy weekend evenings, weekday mornings, and slow midweek afternoons to sense the town’s rhythm.
5. Work with a local agent who knows not just neighborhoods, but the micro-choices — the streets to avoid, the subdivisions that hold value, and the upcoming developments that will affect prices.

Overpriced towns to avoid in Southern Oregon is as much about strategy as it is about geography. Doing the homework and widening your search will save money and improve life quality.

Relocation Resources & Next Steps

If you want more detailed town-by-town breakdowns, we published a free relocation guide that includes school data, commute times, hospital information, climate notes, and even wildfire zone information. Scan the relocation guide QR code from the video or get in touch and I’ll send it to you.

My team helps buyers with tailored searches that pinpoint the communities that best match your needs and budget. Whether you want a quiet river town, an artsy college town, or a suburban neighborhood close to healthcare and airports, we’ll show you both the popular areas and the smart alternatives.

FAQs About the Overpriced Towns to Avoid in Southern Oregon

Aren’t popular towns always the best investment?

Not always. Popular towns like Ashland and Jacksonville hold value because of demand, but that premium is often paid for culture, status, and convenience. If you prioritize daily living needs, access, and affordability, alternatives like Talent, Twin Creeks (Central Point), Grants Pass, Eagle Point, Rogue River, and Shady Cove can be smarter investments and offer better cash flow or equity potential.

How much can I typically save by choosing an alternative?

It varies, but in many cases the alternatives I recommend are $50,000–$200,000 less in median price than the overvalued towns. For example, Twin Creeks (Central Point) shows a median near  $480,000 vs. East Medford at $515,000; Talent at $450,000 vs. Ashland at $580,000; Grants Pass often under $450,000 vs. Jacksonville at $650,000. Those savings can be used for a larger lot, renovations, or lower mortgage payments.

What about wildfire and insurance risk?

Wildfire risk is an important factor in Southern Oregon. Some areas (especially wooded or hillside lots) carry higher insurance premiums or stricter building requirements. Always check fire risk maps, ask for recent insurance quotes, and consider defensible space and landscaping when buying. Many buyers that want peace of mind choose suburbs and river towns that are less heavily forested or have better municipal services.

Are schools significantly different between these towns?

Yes. School quality and options vary by district. Ashland and some Medford schools have well-regarded programs; smaller towns may have fewer specialty programs but smaller class sizes and closer community involvement. If schools are a primary driver, prioritize towns within strong school districts and review school performance data with your agent.

How do I choose between a town with “status” and an affordable alternative?

Start by listing daily non-negotiables and visit each town with those in mind. If you require quick access to specialized healthcare or elite cultural venues, the pricier town may make sense. If your need is family-friendly parks, good schools, and value, an alternative town will probably suit you better. Try living like a local for a weekend—shop, eat out, and talk to residents before deciding.

What’s the best way to start a targeted search?

Work with an agent who understands Southern Oregon’s micro-markets and can show you alternative neighborhoods that match your priorities. Use a list approach—rank towns by commute, price, amenities, and lifestyle—and have your agent pull options in each to do side-by-side comparisons.

Final Thoughts

Southern Oregon is a fantastic place to live, but the most popular towns are not always the best financial or lifestyle choice for everyone.  Overpriced towns to avoid in Southern Oregon by educating yourself on realistic price points, nearby alternatives, and the lifestyle trade-offs you’re comfortable making.

If you want personalized guidance, a deeper dive into school districts, wildfire risk, commute times, or to see homes in any of these areas, reach out. My team and I are local experts who will show you both the popular towns and the under-the-radar options that often deliver better long-term satisfaction and value.

Thanks for reading. If you’d like the relocation guide or to discuss your goals, call or text me at 541-954-7758 — I’m Brian Simmons with the Buying Southern Oregon Real Estate Team, and I’d love to help you find the right place for your next chapter!