1099-s

If you received a Form 1099-S reporting proceeds from the sale of a timeshare as real property, you should report it on your return. Forms 1099-S are reviewed by the IRS information return matching program, and not reporting the sale could lead to your receiving a notice asking for more information or proposing to tax you on the proceeds shown on the form, regardless of whether you received any cash in the transaction.

You will report the sale of a timeshare or second residence in TurboTax Online under Wages and Income, in the Investments section.

1. Scroll down the screen until you come to the section “Investment Income”
2. Choose “Stocks, Mutual Funds, Bonds, Other” and select “Start" or click "Add Investment" if you have already worked on this section
3. Continue. When you see a list of brokerages for import, click Enter a Different Way
4. The next screen has a list of investment types. Click on Other / 1099-S, which includes second homes

See this thread for further discussion on how to report the information on the sale so that TurboTax can calculate the gain. No deduction would be allowed for a loss on the sale of a personally used second residence.