RETIRING IN SOUTHERN OREGON: Where Is the Best Place to Live in Retirement?

RETIRING IN SOUTHERN OREGON: Where Is the Best Place to Live in Retirement?

Did you know that roughly 50,000 people move to Oregon each year? It’s pretty easy to see why, as the state boasts beautiful landscapes, recreational activities, and a great climate and culture for retirees. Not to mention more than 150 wineries, including RoxyAnn WineryDel Rio Vineyards, and Hummingbird Estate.  

If you're thinking about retiring in Southern Oregon, you're in luck – there are lots of great places to choose from! But which one is the best for you? That depends on your needs and wants. 

Do you want a small-town feel, or something more urban? Are you looking for mountains or a coastline? Read on to find out the pros and cons of some of the most popular retirement towns in Southern Oregon.

What to Consider Before Retiring

There's a lot to think about before you retire. This is especially true if you’re thinking about relocating to somewhere like Southern Oregon for retirement. 

While we believe moving to Oregon is never a bad idea, here are a few things to keep in mind when thinking about retirement living in Oregon.

First, consider your financial situation. 

Do you have enough saved up to cover your costs? Will you have any income other than your savings? What kind of lifestyle do you want to maintain in retirement? 

Answering these questions will give you a better idea of how much money you'll need to have saved before you can retire comfortably.

Next, think about your health. 

Are you in good enough health to enjoy a long retirement? Do you have any chronic health conditions that will require ongoing care? What kind of health insurance will you need in retirement? 

Make sure you have a clear picture of your health situation before making any retirement plans.

Finally, consider your personal relationships. 

What role do your family and friends play in your life? Would you like to spend more time with them in retirement? What kinds of activities do you enjoy doing with them? 

Make sure you'll be able to maintain the relationships that are important to you before retiring, especially if you’re planning on moving to Oregon for retirement. While that distance might not seem like a lot now, it can affect your mental health over time.

These are just a few things to think about before retiring. By taking the time to consider all aspects of your life, you can be sure that you're making the best decision.

Reasons to Retire in Southern Oregon

Southern Oregon is a region that has a lot to offer retirees. The climate is mild, there are plenty of outdoor activities to enjoy, and the cost of living is relatively affordable. 

In addition, Southern Oregon is home to a number of retirement communities that provide residents with a supportive and friendly environment. And, no, we’re not just talking about Southern Oregon retirement homes. 

Plenty of towns and neighborhoods in this region of the state cater well to aging communities in terms of activities and quality of life.

Here are just a few of the many reasons why retirees might choose to settle down in Southern Oregon.

Mild Weather

The mild climate is a major draw for many retirees. Southern Oregon enjoys warm summers and cool, dry winters. This means that retirees can enjoy all sorts of outdoor activities throughout the year, from hiking and camping in the summer to skiing and snowshoeing in the winter.

Recreation & Cultural Activities

In addition to its great weather, Southern Oregon also offers ample opportunities for recreation. The region is home to countless hiking trails, biking paths, and waterfalls. 

Retirees can also enjoy all sorts of cultural activities in the cities of Ashland and Medford. From live theaters to art galleries, there’s something for everyone in Southern Oregon.

However, just because you might retire in Southern Oregon, doesn’t mean you’re confined to that part of the state. You can explore all of Oregon, which has plenty to offer retirees.

From hiking and biking to golfing and fishing, there's something for everyone to enjoy. And with so many beautiful scenic locations, you'll never get bored of the scenery.

But it's not all about outdoor activities. There are plenty of indoor activities to keep you busy as well. Visit one of Oregon's many museums or art galleries, catch a show at a local theater, or take a cooking class.


Finally, Southern Oregon is an affordable place to live. Housing costs are relatively low. And, you’ll be delighted to know that Oregon ​​doesn’t tax Social Security benefits.

This makes it an ideal place for retirees who are on a budget, or who want to ensure they can stretch their pension.

What People Like About Southern Oregon

Southern Oregon is a beautiful place that has a lot to offer. Some people like the fact that there are so many different locations to explore, from the coastal town of Brookings to the mountains of Crater Lake National Park. 

Others appreciate the region's diverse climate, which includes beautiful, relaxing temperate rainforests. And, of course, Southern Oregon is also home to some of the best wine country in the state, with dozens of wineries dotting the landscape. 

Whether you're looking for a scenic place to hike or a relaxing place to enjoy a glass of wine, Southern Oregon is sure to have something for you.


The Best Locations in Southern Oregon for Retirement

So we’ve convinced you that retiring in Southern Oregon is right for you? Great! Now, it’s just time to think about where you’ll retire.

While there are numerous great locations in Southern Oregon for retirement, here are four of our top picks.

Retiring in Eagle Point, Oregon

Located six miles northeast of Medford, Oregon, and just forty miles north of the California border, Eagle Point is considered one of the best of small-town America.  

Home to several historic sites like the Butte Flour Mill, premier golf courses (like Eagle Point and Stone Ridge golf clubs), breathtaking waterfalls, and one of three Oregon’s National Cemeteries, this charming town offers a little something for everyone. It’s also just a flat-out beautiful place to live as Eagle Point sits on the edge of the Rogue Valley on your way to several lakes, including Lake of the Woods, Fish Lake, Crater Lake, and Diamond Lake.

There are also several parks and recreation areas, making Eagle Point a great place to enjoy the outdoors. Everything is conveniently located nearby, and most of the town is walkable and pedestrian-friendly, especially the historic downtown district. Perhaps the most appealing quality is the community and how neighborly people are. 

Explore Eagle Point, Oregon homes to envision yourself living here in retirement.

Retiring in Rogue River, Oregon

Rogue River is a charming little town of friendly people and businesses located off Interstate 5, just eight miles from Grants Pass and 30 miles northwest of Medford. Rogue River, Oregon is a place like no other. From its pristine forests to its rushing river, Rogue River is a true natural wonder. And it's not just the scenery that makes Rogue River special – it's also the people. 

The residents of Rogue River are some of the most friendly and welcoming people you'll ever meet. They're always happy to share their love of the area with visitors, and they're always ready to lend a helping hand. 

This river town offers plenty of outdoor adventures and is a perfect spot for someone looking for a small-town living. Rogue River’s warm dry summers with cool evenings and moderate winters provide an opportunity to enjoy country living at its best.

Whether you're looking for an adventure-filled vacation or a relaxing getaway close to your new home, Rogue River is the perfect place for those looking to retire in Southern Oregon.

Explore Rogue River, Oregon homes to envision yourself living here in retirement.

Retiring in Jacksonville, Oregon

Jacksonville is a small town in Southern Oregon that is rich in history. The town was originally founded as a gold mining camp in the 1850s, and it was later an important stop on the stagecoach route between California and Portland. 

Home to the Britt Music and Art Festival and the Jacksonville Art Walk, Jacksonville is now a popular tourist destination with a vibrant cultural scene. The high quality of life, moderate climate, and walkability make Jacksonville an idyllic place to live that reminds residents of what is so special about small-town America.

With a combination of wineries, restaurants, independently-owned shops, it's easy to see what attracts people to Jacksonville. Love to venture out and spend the day sipping some pinot noir? Jacksonville is home to a number of great wineries, including the top-rated DANCIN Vineyards and Oregon's first winery, Valley View Winery.

For active retirees, Jacksonville is located in the midst of beautiful scenery, and there are plenty of outdoor activities to enjoy in the area, such as hiking, biking, and fishing. 

Explore Jacksonville, Oregon homes to envision yourself living here in retirement.

Retiring in Central Point, Oregon

The peaceful and community-oriented Central Point is the first town in the valley. Its name hails from its position in the heart of Rogue Valley. Located just a few miles north of Medford, Central Point is a growing, vibrant and welcoming community of unique shops, local restaurants, and small businesses.  

Central Point is a beautiful place to live, with access to wonderful recreational opportunities like skiing, boating, fishing, hiking, camping, and biking. In addition to outdoor adventure, Central Point is located within minutes of many cultural attractions and a vibrant performing arts scene. 

It is home to the award-winning, internationally known cheese factory, the Rogue Creamery; and the original Grange Co-op. Central Point is also close to the world-renowned Crater Lake, the deepest lake in the U.S. and Oregon’s only national park. 

If you’re looking to explore during your retirement, Central Point is a great place to land. It’s, well, a central point for exploring all that Southern Oregon has to offer.

Explore Center Point, Oregon homes to envision yourself living here in retirement.

How to Find the Right Home in Southern Oregon

With its mild climate, stunning scenery, and an array of amenities, it's no wonder that retirees are flocking to this area of Oregon. 

But with so many choices, how do you know which community is right for you? Here are a few things to consider when searching for the perfect home in Southern Oregon for retirement.

First, think about your budget. Southern Oregon is home to a wide range of communities, from luxurious golf resort communities to more affordable 55+ communities. Knowing how much you can afford to spend will help you narrow down your options.

Next, consider your lifestyle. If you're an active adult who enjoys golfing, hiking, and other outdoor activities, you'll want to find a neighborhood that offers plenty of amenities and activities. On the other hand, if you're looking for a more low-key lifestyle, you might prefer a smaller community with less going on.

Finally, take your time. Retirement is a major life decision, so it's important to choose the community that's right for you. 

Visit different housing communities and cities in the area, talk to current residents and get a feel for each one before making your final decision. With a little time and effort, you're sure to find the perfect Southern Oregon home for your golden years.

Find the Perfect Home for Retiring in Oregon

There’s plenty to consider when retiring, especially if you’re retiring in Southern Oregon from out of state and need to purchase a home here.

To help make the transition as smooth and easy as possible, it helps to work with a trusted real estate agency. Leiser Real Estate Group is here for you.

We are a full-service community-oriented real estate group dedicated to serving the needs of discerning buyers and sellers throughout beautiful Southern Oregon.

Get in touch today to start your home search. 



Patrick and Polina have lived in Southern Oregon for more than a decade. They know – and love – this area and often refer to it as “America’s Best Kept Secret.” Whether you are looking to purchase your dream home, sell your existing property or build your real estate portfolio, this dynamic duo has the insight, creativity, and a clear understanding of the market to ensure your success. While Patrick and Polina work collaboratively throughout the process, you will see that each of them brings something unique and valuable to the team, giving you the competitive advantage in every scenario.