Smart Year-End Tax Strategies for Investors

It's not too late to trim your tax bill for 2014.

The end of the year is rapidly approaching, and that means you have just a few days to reduce your 2014 tax bill. Thanks to the prolonged bull market, many investors are sitting on big gains. Smart year-end planning can reduce the taxes you’ll pay on those gains, along with other types of income.

Start by reviewing your portfolio. If you’re in the 10% or 15% tax bracket, you may be able to sell some of your blockbuster stocks or mutual funds without paying taxes on your long-term gains. For 2014, a married couple with taxable income of up to $73,800 can take advantage of this favorable tax rate.

Investors in higher tax brackets should look for losses to offset their gains. Just be mindful of what’s known as the "wash sale" rule. If you sell stocks or funds at a loss, you must wait at least 30 days before repurchasing them. Otherwise, the IRS will bar you from claiming the loss on your tax return.

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High-income investors can also trim their tax bill by giving appreciated stocks or mutual funds to charity. You can deduct the fair market value of the securities on the day you make the gift, and you’ll never have to pay taxes on your profits. Just be sure to donate shares that you’ve owned for more than a year to qualify.

If your favorite charity can't accept donations of appreciated securities, consider opening what’s called a donor-advised fund instead. The fund administrator will sell the securities for you and add the proceeds to your account. You can deduct the value of the securities on your 2014 tax return and decide later where you want to donate the money.

Yet another option for high-income investors is to give appreciated securities to adult children or parents who are in a lower tax bracket. If they’re in the 10% or 15% bracket, they can sell the securities, tax-free.

Finally, if dips in the stock market have put you in a buying mood, make sure you don’t accidentally buy a big tax bill. In December, many mutual funds pay out dividends and capital gains that have built up during the year. The payouts go to investors who own the funds on what’s known as the ex-dividend date, and the funds’ prices fall by a corresponding amount on that date. If you own a fund in a nonretirement account on the ex-dividend date, you’ll have to pay taxes on those payouts, even if you immediately reinvest the money in extra shares. Check the fund’s Web site to find out when the dividend will be paid, and purchase shares after that date to avoid the unintended tax hit.

Wondering what other tax breaks you might be missing? Check out our list of the most overlooked tax deductions.

Sandra Block
Senior Editor, Kiplinger's Personal Finance

Block joined Kiplinger in June 2012 from USA Today, where she was a reporter and personal finance columnist for more than 15 years. Prior to that, she worked for the Akron Beacon-Journal and Dow Jones Newswires. In 1993, she was a Knight-Bagehot fellow in economics and business journalism at the Columbia University Graduate School of Journalism. She has a BA in communications from Bethany College in Bethany, W.Va.