5 things US boomers should never sell in retirement — even if you really want to get rid of them. How many do you own?

Thomas Kent

Thu, August 27, 2026 at 1:15 PM GMT+3 8 min read

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Retirement can turn anyone into a ruthless declutterer.

Without a regular paycheck coming in, an unwanted investment or troublesome property can begin to look less like an asset and more like a source of ready cash. Selling may simplify your finances, eliminate responsibilities or provide money for something else you would rather enjoy.

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But some assets provide income, diversification, tax advantages or contractual benefits that can be difficult or impossible to recover once they are gone.

1. A diversified stock portfolio during a downturn

A market decline can feel especially frightening during retirement. When you no longer have decades of paychecks ahead of you, selling stocks and moving into cash can seem like the safest available choice.

Unfortunately, it can also lock in losses and prevent your portfolio from participating fully in the eventual recovery.

Fidelity warns that selling stocks early in retirement while markets are falling can have a permanent negative effect on a portfolio (1). This is part of sequence-of-returns risk: Withdrawing from a shrinking portfolio leaves fewer invested assets available to help you recover and support future withdrawals.

That does not mean you should retain an undiversified collection of speculative stocks or more stock exposure than you can tolerate. However, changing your long-term plan solely because markets have fallen can transform a temporary decline into permanent damage.

If you prefer a hands-off, tech-forward approach to maintaining an appropriate investment mix, Vanguard's Digital Advisor puts the investing expertise of one of the world's largest asset managers at your fingertips.

It builds a personalized portfolio using Vanguard's well-known low-cost ETFs and mutual funds, then uses automatic rebalancing to keep your investments aligned with your goals. The platform also provides retirement guidance and allows you to add new financial goals as your life evolves.

With a minimum investment of just $100, professionally guided investing is relatively accessible. For every $10,000 held in an all-index portfolio, you will pay approximately $15 to $16 annually.

You can also test-drive the Vanguard experience without advisory fees for the first 90 days.

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2. A profitable rental property because you are tired of being a landlord

Retirement is supposed to free up your time, not fill it with midnight calls about leaking pipes. It is understandable that some retirees want to sell their rental properties and leave tenants, repairs and vacancies behind.

But a profitable rental can provide something particularly valuable after your employment paychecks stop: recurring income that is not entirely dependent on Social Security or withdrawals from your investment portfolio.

Half of retirees received income from interest, dividends or rentals in 2024, according to the Federal Reserve (2). Those private income sources can supplement benefits and reduce the amount that must be withdrawn from retirement accounts.

Before selling, compare the property's net income with what the proceeds could realistically generate elsewhere after taxes and transaction costs. Hiring a property manager may also be less expensive than permanently giving up a profitable asset.

If the property consistently loses money, requires major repairs or leaves too much of your wealth concentrated in one location, selling may still make sense.

And alternatively, you can tap into the real estate market by investing in shares of vacation homes or rental properties through Arrived.

Backed by world-class investors, including Jeff Bezos, Arrived allows you to invest in shares of vacation and rental properties, earning a passive income stream without the extra work that comes with being the landlord of your own rental property.

To get started, simply browse through its selection of vetted properties, each chosen for its potential appreciation and income generation. Once you select a property, you can start investing with as little as $100.

3. All the gold you own

When gold prices jump, cashing out can be tempting. Taking profits may make sense, especially if gold has become too large a share of your portfolio. But selling every ounce could eliminate a useful source of diversification.

Gold pays no dividends or interest and can lose value, but it may provide a refuge during volatile or inflationary periods (3). Before selling it all, consider whether a modest allocation still has a role.

And if, conversely, you're looking to get some gold exposure, one way to do that while receiving significant tax advantages is to open a gold IRA with the help of Priority Gold.

Gold IRAs allow investors to hold physical gold or gold-related assets within a retirement account. This combines the tax advantages of an IRA with the potential protective benefits of investing in gold, making it an option for those looking to potentially hedge some of their retirement funds against economic uncertainty.

To learn more, you can receive a free information guide containing details about how to get up to $10,000 in free silver on qualifying purchases.

4. Highly appreciated assets intended for your heirs

An investment that has soared in value can carry a sizable tax bill. If stock purchased for $50,000 is now worth $250,000, selling could create a $200,000 taxable gain before adjustments or exclusions.

Inherited assets are treated a bit differently. According to the IRS (4), their basis is generally reset to fair market value at the owner's death, although exceptions apply.

And keeping an appreciated asset doesn't mean the rest of your portfolio has to look just like it. With Willow Wealth, eligible investors can diversify beyond publicly traded stocks and bonds through private-market opportunities spanning real estate, private equity, private credit, art and litigation finance.

Minimum investments start as low as $5,000. You can select individual deals or opt for diversified funds, including funds managed by institutional firms such as Goldman Sachs, Carlyle and StepStone.

More than 500,000 members have invested over $6 billion (5) through Willow and the platforms it has acquired.

Private investments can require long holding periods, carry higher fees and result in losses. See how Willow can put your money to work across a wider range of assets.

5. An annuity before checking its guarantees

You might be tempted to surrender an annuity when you need a lump sum, or get frustrated with its restrictions. However, older contracts may contain guaranteed income, death benefits or other provisions that are costly to replace.

FINRA says variable annuities can carry surrender periods of eight years or longer (6). And cashing one out during that period can trigger surrender charges, while exchanging a contract may cause its owner to forfeit valuable living or death benefits.

Annuities vary enormously. Some are expensive, complicated or no longer suited to their owner's needs, so keeping one forever is not necessarily the answer. Before surrendering or exchanging a contract, make sure to check its fees, guaranteed rate, surrender value, income benefits and potential tax consequences.

You can then compare those features with the annuities available today.

If you decide an annuity still belongs in your retirement plan, Annuity.org (7) can help you compare available options and lock in a competitive rate.

The process takes three steps: explain your retirement goals, review suitable annuity options and select the contract that fits your needs. Right now, you could get fixed annuity rates as high as 6.9%.

Depending on the contract, an annuity can create a stream of guaranteed income that continues for the rest of your life. Rates and benefits vary, while guarantees depend on the issuing insurer's financial strength.

You can get started with a free retirement income consultation to compare your options.