If you are researching the best cities for retiring in Oregon, the right answer depends on three things: your budget, the lifestyle you want day to day, and how important it is to be close to healthcare, grocery stores, and other essentials. Oregon has real advantages for retirees, including no sales tax and no Oregon tax on Social Security benefits, but it also comes with tradeoffs like wet winters in much of western Oregon, and higher costs in some of the state’s more desirable communities.
Oregon’s appeal is easy to understand. Many of the best cities for retiring in Oregon have options for every lifestyle. You can choose from accessible urban neighborhoods, quiet suburban communities, historic river towns, wine-country access, mountain recreation, or coastal living. At the same time, Oregon is not equally convenient everywhere. Healthcare access is strongest in major hubs and metro corridors like Portland, Salem and Eugene, while more rural and coastal communities can offer beauty and peace at the cost of fewer nearby services.
That is why the best cities for retiring in Oregon aren't straightforward: this is a matter of opinion and desires. The number one reason retirees make a move is to be closer to family and friends, so if that is the genesis of your decision, the best cities for retiring in Oregon are probably the ones closest to your loved ones. The strongest retirement locations usually balance housing costs with daily livability: reliable medical care, reasonable access to groceries and errands, manageable transportation, and a lifestyle that keeps you engaged and enlightened as the years pass.
Local Guides for Retiring In Oregon:
Oregon is arguably one of the most beautiful and diverse states in our nation. With such variety in climate and ecology that you really can find something for everyone here. But, when evaluating the best cities for retiring in Oregon, it is important to look beyond home prices and ask a more practical question: what will it actually cost to live there year after year? Let's dive into the benefits of the ALL the best cities for retiring in Oregon:
- Oregon doesn't tax social security benefits. 8 states in our nation do tax these benefits, but Oregon isn't one of them.
- Oregon doesn't have a sales tax. Oregon is one of 5 states that doesn't have a sales tax.
- Oregon doesn't have an inheritance tax which can help protect anything you leave to your loved ones or to charity.
- Oregon doesn't have a gift tax but there is a federal gift tax on anything over $19,000 per recipient in 2026. So keep it under 19k and there won't be a tax.
- Oregon has the lowest average premium for Medicare part D in the country.
- 20% of Oregonians are age 65 or older. Retirees love Oregon for many reasons.
- Retirees age 62 or older can apply for Oregon's Senior Tax Deferral Program. It is a statewide program you can read more about here: Oregon Senior Tax Deferral Program
The Cons of Retiring in Oregon
- Oregon has an estate tax filing threshold that starts at $1 million in gross estate value, which with property values in Oregon being some of the highest in the nation, this metric is easier than most think to hit. This doesn't only matter for higher-net-worth households doing retirement and legacy planning if you have a higher value property. Your estate will be subject to an estate tax of 10% to 16% unless it is in a tax sheltered trust. Contact us for a referral to our preferred estate planning professionals.
- Oregon is frequently listed as one of the most expensive states for basic costs of living. Home prices, energy prices and grocery costs are all taken into consideration to compare with other states. Former Financial Advisor and Author of the book "Real Wealth: Make Money Work for You" Tyler Gardener even considers Oregon the #1 worst state to retire in based on costs.
These lists of pros and cons are statewide metrics. There are also county and city level metrics to consider as well. The city level metrics are included in the local guides above, but let's compare the 3 most heavily populated counties in Oregon:
- Multnomah County: The Oregon Department of Revenue’s FY 2024–25 data shows average effective AV tax rates of $23.56 per $1,000 in Multnomah County
- Washington County: The Oregon Department of Revenue’s FY 2024–25 data shows average effective AV tax rates of $17.96 per $1,000 in Washington County
- Clackamas County: The Oregon Department of Revenue’s FY 2024–25 data shows average effective AV tax rates of $17.68 per $1,000 in Clackamas County
These are just the property tax costs in these counties. It is important to also be aware of Multnomah County’s Preschool for All tax, Metro’s Supportive Housing Services tax and Portland residents also owe a $35 Arts Tax if they meet the income rules. These are exactly the kinds of local overlays that make a city look more affordable on paper than it feels in real retirement. "Metro" isn't just portland, it expands into each of the above counties. So make sure you understand the true costs involved in choosing the best cities for retiring in Oregon.
Living In The Best Cities For Retiring in Oregon Depend On Your Budget
If this all sounds like the best cities for retiring in Oregon are outside of your budget, maybe you're looking at your finances from the wrong angle. The best savers are usually the worst spenders and retirement is about using the funds you have saved but in a smart and balanced way that will support your lifestyle for the long haul. If you're 55 or older, it's time to consider how a reverse mortgage for purchase could make choosing a city to move to from the list of the best cities for retiring in Oregon sound more feasible. Buying a home without monthly mortgage payments and keeping more cash for yourself might be the tool you need to make your move. Learn more about using a reverse mortgage loan to purchase a new home on our website here: Purchasing a New Home With a Reverse Mortgage
