If you are considering moving to Southern Oregon, this guide is written to help you pick the right city for your lifestyle, budget, and priorities. Southern Oregon covers a surprising variety of small cities and towns—each with its own personality. Some places are lively hubs with full amenities, others are quieter, more rural communities, and a few carry challenges that might make them a poor fit depending on what matters most to you. Below I break down the strengths and trade offs of Medford, Ashland, Central Point, Grants Pass, Eagle Point, Jacksonville, and Rogue River so you can decide where you should and should not be looking when moving to Southern Oregon.

Table of Contents

• Introduction
• Medford Overview: The Hub of Southern Oregon
• Ashland Overview: The Cultural Hub of Southern Oregon
• Central Point: Family-Friendly Living
• Grants Pass: Affordable Housing and Outdoor Activities
• Eagle Point: Golf Community and Rural Living
• Jacksonville: Historic Charm and Wine Country
• Rogue River: Small Town Charm and Strong Community
• Practical Checklist Before Moving to Southern Oregon
• How to Narrow Your Search
• Final Thoughts on Choosing the Right Town
• FAQs

Introduction

Choosing the right place matters. Picking the wrong neighborhood can leave you wanting to list your house shortly after you arrive. The goal is to get you comfortable, happy, and settled—without a rushed resale. This overview focuses on practical facts and local flavor so you can narrow your search intelligently before making any major moves.

Medford Overview: The Hub of Southern Oregon

Medford is the largest city in the region, about 85,000 people, and functions as the central hub. If you value convenience—air travel, regional medical centers, big-box shopping, highways—Medford delivers. Rogue Valley International Airport, the Rogue Valley Mall, and the concentration of health care facilities make Medford the go-to city for many who are moving to Southern Oregon.

Medford Pros: Community, Amenities, and Accessibility

Why people pick Medford:

• Widest variety of neighborhoods and price points—from East Medford higher-end sections to more affordable pockets in West Medford.
• All major amenities are nearby: hospitals, shopping, dining, and easy freeway access on I-5.
• Good balance of suburban life and city services without the stress of big-city congestion.

For families and professionals who need access to schools, hospitals, and reliable services, Medford is often the first stop when moving to Southern Oregon. The trade off is price—some parts of Medford are pricier than nearby towns—but relative to big metros the traffic and congestion here are minimal. As one local puts it, what counts as congestion here might be just a few cars at a stoplight.

"What's traffic here and congestion here is like four people in front of you at a stoplight."

Medford Cons: Property Prices and Traffic

Medford offers convenience at a cost. Prices in East Medford can be significantly higher than neighboring areas. Because it is the largest city in the valley, it experiences construction, occasional roadwork, and a busier pace than some smaller towns. If you crave quieter rural living, Medford might feel like too much—but if you are coming from larger metro areas, the city still feels relaxed.

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Ashland Overview: The Cultural Hub of Southern Oregon

Ashland is a compact, vibrant town known for culture, parks, and an exceptional food scene. Home to Southern Oregon University and the Oregon Shakespeare Festival, Ashland attracts people who want arts, dining, and outdoor access all in one place. Population sits around 21,000, making it lively but not sprawling.

Ashland's Culinary Scene: Best Food in Southern Oregon

Ashland consistently ranks as the best place for food in the region. Renowned restaurants, farm-to-table options, and specialty cafes make it a culinary destination. That great food, combined with parks like Lithia Park and dramatic views of the Cascades, draws newcomers who want a culturally rich small-city lifestyle.

Ashland Downsides: High Costs and Congestion

Considerations before moving to Southern Oregon and choosing Ashland:

• Cost: Ashland is one of the most expensive parts of the region. Expect to pay premiums for location, views, and proximity to cultural amenities.
• Parking and crowds: Downtown and the plaza can get busy—especially during festival season—so parking and quick errands can become more time consuming.
• Tourism: Events and festivals bring visitors; that is great for local businesses but can feel touristy during peak months.

If arts, dining, and scenic living are top priorities, the extra cost often feels worth it. But if budget or easy parking matter more, evaluate nearby alternatives.

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Central Point: Family-Friendly Living

Central Point is a steadily growing, family-oriented town just outside Medford. Historically modest, the downtown has seen thoughtful updates that make the area feel fresh and attractive. New residential developments and parks appeal to families who want safe neighborhoods, accessible schools, and community events.

Central Point Growth: A Town on the Rise

Why Central Point is attractive:

• Strong public schools and lots of parks make it ideal for families.
• Economic growth: businesses like Costco and new Amazon facilities chose Central Point for regional presence.
• Convenient county fairgrounds and Expo site means concerts, trade shows, and seasonal events are easy to attend.

Central Point tends to be quieter at night than Medford or Ashland. If you want an early- to mid-day social scene and family-focused neighborhoods, Central Point often hits the right note.

Central Point Cons: Suburban Feel and Quiet Nights

Expect a suburban atmosphere with limited nightlife. Downtown activities taper off earlier than in Ashland or Jacksonville, so if late-night restaurants, bars, or cultural events are essential, Central Point might feel too calm.

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Grants Pass: Affordable Housing and Outdoor Activities

Grants Pass is the second largest city in the region, located in Josephine County about a 25 to 30 minute drive from Medford on I-5. Known for the Rogue River, Grants Pass offers outstanding riverfront living and more affordable housing options compared with Jackson County towns.

Grants Pass Downsides: Job Market and Homelessness

Strengths:

• More riverfront homes and outdoor recreation opportunities—rafting, fishing, hiking—than most other towns.
• Many newer developments target median and lower price points, giving buyers affordable, quality options.

Trade offs:

• Job market: Fewer local employment opportunities than Medford. Many residents commute into Jackson County for work.
• Homelessness: Grants Pass and Medford have been the most visible for homeless encampments in the region. The situation has been changing with new law enforcement and state policy shifts, but it remains a local issue to watch when moving to Southern Oregon.

For buyers prioritizing affordability and outdoor lifestyle, Grants Pass frequently makes the shortlist. Just factor in commute time if you plan to work in Medford and assess how community issues like homelessness influence your comfort.

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Eagle Point: Golf Community and Rural Living

Eagle Point sits north of Medford and is known for its golf course and scenic, semi-rural neighborhoods. It is a short drive to Medford yet offers a quieter pace and more usable land—ideal for gardeners, hobbyists, or anyone wanting a yard without losing easy access to city amenities.

Eagle Point Cons: Distance from Medford

The main compromise is distance. Eagle Point is about 15 minutes from Medford, which is not long, but you should expect occasional drives into the city for specialty medical care or shopping. Many residents appreciate the trade off for large lots, good golf course living, and a strong community feel.

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Jacksonville: Historic Charm and Wine Country

Jacksonville is a beautifully preserved historic town with a strong downtown vibe, excellent restaurants, and close access to Applegate Valley wineries. Founded in 1853, Jacksonville holds a special place for people who appreciate history, walkable main streets, and seasonal festivals. It is also one of the priciest towns in the region, matching Ashland on cost.

Jacksonville Cons: High Property Prices

Expect to pay a premium for location and character. A move-in-ready three bedroom home in Jacksonville will often push toward the high six figures, and larger or historic properties can sell for well over a million. For retirees or buyers searching for small-town charm and great dining, Jacksonville is a top pick. For those on tighter budgets, it may be out of reach.

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Rogue River: Small Town Charm and Strong Community

Rogue River is a smaller town with a big heart. Centrally located between Medford and Grants Pass, Rogue River offers the convenience of nearby cities while preserving a genuine small-town vibe. Stores, doctors, and everyday services are available locally, so routine errands do not require a long drive.

Residents often mention the friendliness and neighborly support as a defining characteristic. Community members rally to help in emergencies, volunteers are visible, and local traditions—like lining the streets with flags for holidays—create a strong sense of belonging.

Practical Checklist Before Moving to Southern Oregon

Use this checklist to figure out which town matches your needs:

• Work commute: Will you be working locally or commuting? Medford has the most job options.
• Budget: Ashland and Jacksonville are the most expensive. Grants Pass and parts of Central Point often have more affordable inventory.
• Lifestyle: Want nightlife and culture? Ashland and Jacksonville. Prefer quiet and yards? Eagle Point or Rogue River.
• Outdoor access: Grants Pass excels for riverfront and coastal proximity; Ashland offers mountains and trails nearby.
• Community priorities: If schools and family parks are top priorities, Central Point and Medford neighborhoods shine.

How to Narrow Your Search

Be deliberate. When moving to Southern Oregon, visit each town at different times of day and on weekends. Drive neighborhoods. Test the commute. Try a local coffee shop or farmer's market. Pay attention to noise, parking, and how comfortable you feel on routine errands. Those simple, practical tests reveal more than photos or listing pages.

Local Realities That Matter

Some realities are important to face up front:

• Housing inventory fluctuates: Popular small towns sell quickly. Prepare financing and know your priorities.
• Homelessness is a regional issue: Medford and Grants Pass have been the most visible, but the scale is much smaller than major West Coast metros.
• Rural fire risk and preparedness: In dryer months, wildland fire awareness and defensible-space considerations matter for many properties.

Understanding these realities will help you avoid surprises and set realistic expectations while moving to Southern Oregon.

Final Thoughts on Choosing the Right Town

There is no one-size-fits-all answer when moving to Southern Oregon. If convenience, medical access, and variety top your list, Medford is an excellent hub. If culture, dining, and a university town vibe matter most, Ashland earns its reputation. For affordability and river-focused outdoor living, Grants Pass shines. Eagle Point is great for golf or semi-rural land. Central Point gives families parks and community growth. Jacksonville delivers historic charm and wine-country living, and Rogue River offers an unbeatable small-town sense of community with easy access to both Medford and Grants Pass.

Make a priorities list, visit multiple towns, and compare what matters most to your daily life. Thoughtful research will help you avoid buying in the wrong place and ensure your move to Southern Oregon is a long-term success.

If you need to buy a home in Southern Oregon, contact me — call or text 541-827-8767  and I’ll help you find the right place.

FAQs

How do I choose the best town when moving to Southern Oregon?

List your top priorities—commute, budget, schools, outdoor access, and cultural amenities—then visit each town that matches at least two of those priorities. Spend time in neighborhoods and on errands to see how daily life feels before deciding.

Which Southern Oregon towns are the most affordable?

Grants Pass and certain neighborhoods in Central Point and West Medford generally offer more affordable housing options than Ashland or Jacksonville. New developments often target median price points outside of the premium towns.

Are there good job opportunities in Southern Oregon?

Medford has the strongest local job market in the region, with larger health care providers and retail/warehouse employers. Grants Pass has fewer local jobs, and some residents commute to Medford for work.

How big of a concern is homelessness when moving to Southern Oregon?

Medford and Grants Pass have been the most visible locations for homelessness in the region. It is less pronounced than in major West Coast cities, but it has become more noticeable in the last decade. Local policy and enforcement changes are expected to address the issue over time.

Which town is best for retirees thinking about moving to Southern Oregon?

Ashland and Jacksonville are particularly popular with retirees because of cultural activities, dining, and scenic surroundings. Rogue River and Eagle Point also appeal to retirees seeking a quieter pace with local conveniences.

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