TL;DR: Oregon’s scenic beauty, tax advantages, and diverse communities make it a standout choice for retirees. This guide to the best places to retire in Oregon explores top cities and towns based on cost of living, lifestyle, healthcare access, and overall quality of life—helping you find the right fit for your retirement goals.
Main points:
- Key tax benefits, including no tax on Social Security and no state sales tax
- City comparisons featuring Ashland, Bend, Portland, Eugene, and more
- Affordable options like Ontario and Roseburg for stretching retirement income
- Luxury and active lifestyle destinations such as Lake Oswego and Bend
- Important planning factors, including budget, healthcare, climate, and proximity to family
Oregon offers scenic landscapes, mild weather, and friendly communities. Is Oregon a good place to retire? You’ll find great outdoor adventures, cultural richness, and even peaceful, relaxing spots.
Is Oregon a Good Place to Retire?
If you're wondering where to retire in Oregon, this guide highlights the best places to retire in Oregon based on cost of living, lifestyle, healthcare access, and community feel. Here’s why:
- Oregon does not tax Social Security benefits
- Property taxes are lower than in many states
- Some retirement income qualifies for tax exemptions
- The state income tax applies to other income types
Ashland
Average Cost of a Home: $560,654
Population: 21,360
Cost of Living: 6.1% higher than the US average
Ashland, a charming city popular among retirees, is known for its vibrant arts scene. Ashland offers a warm atmosphere and manageable living costs. Many retirees enjoy its blend of culture and outdoor recreation. Consider these factors:
- Home to the Oregon Shakespeare Festival
- Surrounded by mountains and forests
- Popular for hiking and bird-watching
- Strong healthcare access
- Active senior community
Bend
Average Cost of a Home: $747,228
Population: 99,178
Cost of Living: 27.0% higher than the US average
Bend attracts retirees who enjoy nature and an active lifestyle. Consider:
- Close to the Cascade Mountains
- Fishing, skiing, and golf nearby
- Community workshops and senior programs
- Quality healthcare facilities
- Variety of housing options
Portland
Average Cost of a Home: $547,575
Population: 652,503
Cost of Living: 27.7% higher than the US average
Portland appeals to retirees seeking urban living and it’s the best city to retire in Oregon. It has diverse Its diverse amenities offset Portland's higher living costs, making it an attractive retirement option for those seeking a vibrant lifestyle.
- Think about this:
Museums, theaters, and restaurants - Large park system and botanical gardens (serene spaces for relaxation)
- Extensive healthcare network
- Senior clubs and social organizations (opportunities to meet people, pursue hobbies, and engage in community events)
Grants Pass
Average Cost of a Home: $407,014
Population: 39,189
Cost of Living: 2.5% higher than the US average
Grants Pass offers retirees small-town charm and outdoor adventures. Think about:
- Located along the Rogue River
- Fishing, rafting, and hiking
- Local hospital and clinics
- Lower housing costs than major cities
Lake Oswego
Average Cost of a Home: $920,998
Population: 40,731
Cost of Living: 33.7% higher than the US average
Lake Oswego, an upscale suburb, offers a luxurious Oregon retirement. It’s known for its high living standards, beautiful homes, and well-kept neighborhoods. It’s definitely one of the best Oregon cities to retire in if you want a premium experience. Many retirement communities with high-end amenities are also available, making it one of the best places to retire in Oregon. Lake Oswego's high cost of living is offset by its quality of life, amenities, and beautiful setting., so consider:
- Beautiful neighborhoods
- High-end retirement communities
- Art galleries and community events
- Strong healthcare access and support services for seniors.
Many retirement communities with high-end amenities are also available, making it one of the best places to retire in Oregon.
Eugene
Average Cost of a Home: $478,322
Population: 176,654
Cost of Living: 6.6% higher than the US average
Eugene is an attractive city for Oregon retirement, especially if you value a vibrant community life. You could benefit from:
- Parks and walking trails
- Willamette River access (beautiful trails and parks along its banks)
- Senior-focused clubs and activities (stay connected and involved)
- Multiple hospitals and clinics
Ontario
Average Cost of a Home: $290,526
Population: 11,645
Cost of Living: 19.9% lower than the US average
Ontario is one of many places that come to mind when you think of retirement destinations. It charm makes it one of the best towns to retire in Oregon. It a great place for those who want to stretch their income:
- Located on the Oregon–Idaho border
- Strong agricultural community
- Slower pace of life
- Lower living costs
Roseburg
Average Cost of a Home: $351,882
Population: 23,683
Cost of Living: 10.5% lower than the US average
Roseburg, situated in Umpqua Valley, is a great place to retire in Oregon. Natural beauty and surrounding community make it perfect for those seeking a peaceful retirement.
A major benefit of retiring in Roseburg is its low cost of living compared to other Oregon areas. Thanks to affordable housing and reasonable expenses for healthcare, transportation, and utilities, retirees can live comfortably without straining their finances.
Consider:
- Forested hills and vineyards
- Mild year-round climate
- Winery events and tastings
- Affordable housing
A major benefit of retiring in Roseburg is its low cost of living compared to other Oregon areas. Thanks to affordable housing and reasonable expenses for healthcare, transportation, and utilities, retirees can live comfortably without straining their finances.
King City
Average Cost of a Home: $473,548
Population: 23,683
Cost of Living: 28.1% higher than the US average
King City, Oregon, is highly regarded as a top retirement destination due to its affordability, zero percent sales tax rate, and proximity to Portland's extensive amenities. Consider:
- No sales tax
- Close to Portland amenities
- Golf course and hiking trails
- Strong community events
Harbor
Average Cost of a Home: $499,918
Population: 4,919
Cost of Living: 0.4% lower than the US average
Harbor, located along the beautiful southern Oregon coast, offers retirees a serene, picturesque setting with a mild climate. It’s one of the best places to retire in Oregon if you’re looking to maximize retirement savings while enjoying the coastal lifestyle.
- Southern Oregon coast location
- Ocean views and mild climate
- Close-knit community
- Lower living costs than urban areas
Planning Your Retirement in Oregon
Choosing where to retire in Oregon depends on:
- Budget
- Healthcare needs
- Lifestyle preferences
- Proximity to family
- Climate
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Stewart Willis is the founder and president of Asset Preservation Wealth & Tax, a financial planning firm in Phoenix, Arizona. Investment advisory services offered through Foundations Investment Advisors, LLC, an SEC registered investment adviser.
A Roth conversion may not be suitable for your situation. The primary goal in converting retirement assets into a Roth IRA is to reduce the future tax liability on the distributions you take in retirement, or on the distributions of your beneficiaries. The information provided is to help you determine whether or not a Roth IRA conversion may be appropriate for your particular circumstances. Please review your retirement savings, tax, and legacy planning strategies with your legal/tax advisor to be sure a Roth IRA conversion fits into your planning strategies.
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