Table of Contents
- Introduction
- Topics - This chapter discusses:
- Useful Items - You may want to see:
- What Is a Sale or Trade?
- Basis of Investment Property
- How To Figure Gain or Loss
- Nontaxable Trades
- Transfers Between Spouses
- Related Party Transactions
- Capital Gains and Losses
- Terms you may need to know (see Glossary):
- Capital or Ordinary Gain or Loss
- Holding Period
- Nonbusiness Bad Debts
- Short Sales
- Wash Sales
- Options
- Straddles
- Sales of Stock to ESOPs or Certain Cooperatives
- Rollover of Gain From Publicly Traded Securities
- Gains on Qualified Small Business Stock
- Rollover of Gain From Sale of Empowerment Zone Assets
- Reporting Capital Gains and Losses
- Special Rules for Traders in Securities
This chapter explains the tax treatment of sales and trades of investment property.
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Sale of your main home, discussed in Publication 523, Selling Your Home,
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Installment sales, covered in Publication 537, Installment Sales,
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Various types of transactions involving business property, discussed in Publication 544, Sales and Other Dispositions of Assets,
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Transfers of property at death, covered in Publication 559, Survivors, Executors, and Administrators, and
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Disposition of an interest in a passive activity, discussed in Publication 925, Passive Activity and At-Risk Rules.
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What a sale or trade is,
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Basis,
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Adjusted basis,
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Figuring gain or loss,
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Nontaxable trades,
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Capital gains and losses, and
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How to report your gain or loss.
Publication
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551 Basis of Assets
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564 Mutual Fund Distributions
Form (and Instructions)
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Schedule D (Form 1040)
Capital Gains and Losses -
6781
Gains and Losses From Section 1256 Contracts and Straddles -
8582
Passive Activity Loss Limitations -
8824
Like-Kind Exchanges
See chapter 5 for information about getting these publications and forms.
| Equity option |
| Futures contract |
| Marked to market |
| Nonequity option |
| Options dealer |
| Regulated futures contract |
| Section 1256 contract |
| Short sale |
This section explains what is a sale or trade. It also explains certain transactions and events that are treated as sales or trades.
A sale is generally a transfer of property for money or a mortgage, note, or other promise to pay money.
A trade is a transfer of property for other property or services, and may be taxed in the same way as a sale.
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The redemption is not essentially equivalent to a dividend — see Dividends and Other Corporate Distributions in chapter 1,
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There is a substantially disproportionate redemption of stock,
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There is a complete redemption of all the stock of the corporation owned by the shareholder, or
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The redemption is a distribution in partial liquidation of a corporation.
Stocks, stock rights, and bonds (other than those held for sale by a securities dealer) that became worthless during the tax year are treated as though they were sold on the last day of the tax year. This affects whether your capital loss is long-term or short-term. See Holding Period, later.
If you are a cash basis taxpayer and make payments on a negotiable promissory note that you issued for stock that became worthless, you can deduct these payments as losses in the years you actually make the payments. Do not deduct them in the year the stock became worthless.
You are treated as having made a constructive sale when you enter into certain transactions involving an appreciated financial position (defined later) in stock, a partnership interest, or certain debt instruments. You must recognize gain as if the position were disposed of at its fair market value on the date of the constructive sale. This gives you a new holding period for the position that begins on the date of the constructive sale. Then, when you close the transaction, you reduce your gain (or increase your loss) by the gain recognized on the constructive sale.
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Enter into a short sale of the same or substantially identical property,
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Enter into an offsetting notional principal contract relating to the same or substantially identical property,
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Enter into a futures or forward contract to deliver the same or substantially identical property (including a forward contract that provides for cash settlement), or
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Acquire the same or substantially identical property (if the appreciated financial position is a short sale, an offsetting notional principal contract, or a futures or forward contract).
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You closed the transaction on or before the 30th day after the end of your tax year.
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You held the appreciated financial position throughout the 60-day period beginning on the date you closed the transaction.
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Your risk of loss was not reduced at any time during that 60-day period by holding certain other positions.
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Any position from which all of the appreciation is accounted for under marked to market rules, including section 1256 contracts (described later under Section 1256 Contracts Marked to Market).
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Any position in a debt instrument if:
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The position unconditionally entitles the holder to receive a specified principal amount,
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The interest payments (or other similar amounts) with respect to the position are payable at a fixed rate or a variable rate described in Regulations section 1.860G-1(a)(3), and
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The position is not convertible, either directly or indirectly, into stock of the issuer (or any related person).
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Any hedge with respect to a position described in (2).
If you hold a section 1256 contract at the end of the tax year, you generally must treat it as sold at its fair market value on the last business day of the tax year.
A section 1256 contract is any:
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Regulated futures contract,
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Foreign currency contract,
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Nonequity option,
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Dealer equity option, or
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Dealer securities futures contract.
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Provides that amounts that must be deposited to, or can be withdrawn from, your margin account depend on daily market conditions (a system of marking to market), and
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Is traded on, or subject to the rules of, a qualified board of exchange. A qualified board of exchange is a domestic board of trade designated as a contract market by the Commodity Futures Trading Commission, any board of trade or exchange approved by the Secretary of the Treasury, or a national securities exchange registered with the Securities and Exchange Commission.
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Requires delivery of a foreign currency that has positions traded through regulated futures contracts (or settlement of which depends on the value of that type of foreign currency),
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Is traded in the interbank market, and
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Is entered into at arm's length at a price determined by reference to the price in the interbank market.
Warrants based on a stock index that are economically, substantially identical in all material respects to options based on a stock index are treated as options based on a stock index.
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Is an equity option,
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Is bought or granted by that dealer in the normal course of the dealer's business activity of dealing in options, and
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Is listed on the qualified board of exchange where that dealer is registered.
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To buy or sell stock, or
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That is valued directly or indirectly by reference to any stock or narrow-based security index.
Equity options include options on a group of stocks only if the group is a narrow-based stock index.
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Is entered into by the dealer (or, in the case of an option, is purchased or granted by the dealer) in the normal course of the dealer's activity of dealing in this type of contract (or option), and
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Is traded on a qualified board or exchange (as defined under Regulated futures contract, earlier.)
A section 1256 contract that you hold at the end of the tax year will generally be treated as sold at its fair market value on the last business day of the tax year, and you must recognize any gain or loss that results. That gain or loss is taken into account in figuring your gain or loss when you later dispose of the contract, as shown in the example under 60/40 rule, below.
Example.
On June 23, 2006, you bought a regulated futures contract for $50,000. On December 31, 2006 (the last business day of your tax year), the fair market value of the contract was $57,000. You recognized a $7,000 gain on your 2006 tax return, treated as 60% long-term and 40% short-term capital gain.
On February 2, 2007, you sold the contract for $56,000. Because you recognized a $7,000 gain on your 2006 return, you recognize a $1,000 loss ($57,000 - $56,000) on your 2007 tax return, treated as 60% long-term and 40% short-term capital loss.
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The net capital loss for your tax year determined by taking into account only the gains and losses from section 1256 contracts, or
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The capital loss carryover to the next tax year determined without this election.
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The capital gain net income for the carryback year determined by taking into account only gains and losses from section 1256 contracts, or
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The capital gain net income for that year.
Figure your net section 1256 contracts gain for any carryback year without regard to the net section 1256 contracts loss for the loss year or any later tax year.
If you disposed of regulated futures or foreign currency contracts in 2007 (or had unrealized profit or loss on these contracts that were open at the end of 2006 or 2007), you should receive Form 1099-B, or an equivalent statement, from your broker.
The marked to market rules, described earlier, do not apply to hedging transactions. A transaction is a hedging transaction if both of the following conditions are met.
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You entered into the transaction in the normal course of your trade or business primarily to manage the risk of:
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Price changes or currency fluctuations on ordinary property you hold (or will hold), or
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Interest rate or price changes, or currency fluctuations, on your current or future borrowings or ordinary obligations.
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You clearly identified the transaction as being a hedging transaction before the close of the day on which you entered
into it.
This hedging transaction exception does not apply to transactions entered into by or for any syndicate. A syndicate is a partnership, S corporation, or other entity (other than a regular corporation) that allocates more than 35% of its losses to limited partners or limited entrepreneurs. A limited entrepreneur is a person who has an interest in an enterprise (but not as a limited partner) and who does not actively participate in its management. However, an interest is not considered held by a limited partner or entrepreneur if the interest holder actively participates (or did so for at least 5 full years) in the management of the entity, or is the spouse, child (including a legally adopted child), grandchild, or parent of an individual who actively participates in the management of the entity.
Gains and losses derived in the ordinary course of a commodity or option dealer's trading in section 1256 contracts and property related to these contracts are included in net earnings from self-employment. In addition, the rules relating to contributions to self-employment retirement plans apply. For information on retirement plan contributions, see Publication 560, Retirement Plans for Small Business, and Publication 590, Individual Retirement Arrangements (IRAs).
Basis is a way of measuring your investment in property for tax purposes. You must know the basis of your property to determine whether you have a gain or loss on its sale or other disposition.
Investment property you buy normally has an original basis equal to its cost. If you get property in some way other than buying it, such as by gift or inheritance, its fair market value may be important in figuring the basis.
The basis of property you buy is usually its cost. The cost is the amount you pay in cash, debt obligations, or other property or services.
There are times when you must use a basis other than cost. In these cases, you may need to know the property's fair market value or the adjusted basis of the previous owner.
If you receive investment property for services, you must include the property's fair market value in income. The amount you include in income then becomes your basis in the property. If the services were performed for a price that was agreed to beforehand, this price will be accepted as the fair market value of the property if there is no evidence to the contrary.
If you received investment property in trade for other property, the basis of the new property is its fair market value at the time of the trade unless you received the property in a nontaxable trade.
Example.
You trade A Company stock for B Company stock having a fair market value of $1,200. If the adjusted basis of the A Company stock is less than $1,200, you have a taxable gain on the trade. If the adjusted basis of the A Company stock is more than $1,200, you have a deductible loss on the trade. The basis of your B Company stock is $1,200. If you later sell the B Company stock for $1,300, you will have a gain of $100.
If you have a nontaxable trade, you do not recognize gain or loss until you dispose of the property you received in the trade. See Nontaxable Trades, later.
The basis of property you received in a nontaxable or partly nontaxable trade is generally the same as the adjusted basis of the property you gave up. Increase this amount by any cash you paid, additional costs you had, and any gain recognized. Reduce this amount by any cash or unlike property you received, any loss recognized, and any liability of yours that was assumed or treated as assumed.
If property is transferred to you from your spouse (or former spouse, if the transfer is incident to your divorce), your basis is the same as your spouse's or former spouse's adjusted basis just before the transfer. See Transfers Between Spouses, later.

To figure your basis in property that you received as a gift, you must know its adjusted basis to the donor just before it was given to you, its fair market value at the time it was given to you, the amount of any gift tax paid on it, and the date it was given to you.
Example.
You receive a gift of investment property having an adjusted basis of $10,000 at the time of the gift. The fair market value at the time of the gift is $9,000. You later sell the property for $9,500. You have neither gain nor loss. Your basis for figuring gain is $10,000, and $9,500 minus $10,000 results in a $500 loss. Your basis for figuring loss is $9,000, and $9,500 minus $9,000 results in a $500 gain.
Example 1.
You were given XYZ Company stock in 1976. At the time of the gift, the stock had a fair market value of $21,000. The donor's adjusted basis was $20,000. The donor paid a gift tax of $500 on the gift. Your basis for gain or loss is $20,500, the donor's adjusted basis plus the amount of gift tax paid.
Example.
In 2007, you received a gift of property from your mother. At the time of the gift, the property had a fair market value of $101,000 and an adjusted basis to her of $40,000. The amount of the gift for gift tax purposes was $89,000 ($101,000 minus the $12,000 annual exclusion), and your mother paid a gift tax of $21,000. You figure your basis in the following way:
| Fair market value | $101,000 |
| Minus: Adjusted basis | 40,000 |
| Net increase in value of gift | $61,000 |
| Gift tax paid | $21,000 |
| Multiplied by .685 ($61,000 ÷ $89,000) | .685 |
| Gift tax due to net increase in value | $14,385 |
|
Plus: Adjusted basis of property to
your mother |
40,000 |
| Your basis in the property | $54,385 |
If you inherited property, your basis in that property generally is its fair market value (its appraised value on the federal estate tax return) on:
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The date of the decedent's death, or
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The later alternate valuation date if the estate qualifies for, and elects to use, alternate valuation.
If no federal estate tax return was filed, use the appraised value on the date of death for state inheritance or transmission taxes.
Before you can figure any gain or loss on a sale, exchange, or other disposition of property or figure allowable depreciation, depletion, or amortization, you usually must make certain adjustments (increases and decreases) to the basis of the property. The result of these adjustments to the basis is the adjusted basis.
Adjustments to the basis of stocks and bonds are explained in the following discussion. For information about other adjustments to basis, see Publication 551.
The basis of stocks or bonds you own generally is the purchase price plus the costs of purchase, such as commissions and recording or transfer fees. If you acquired stock or bonds other than by purchase, your basis is usually determined by fair market value or the previous owner's adjusted basis as discussed earlier under Basis Other Than Cost.
The basis of stock must be adjusted for certain events that occur after purchase. For example, if you receive more stock from nontaxable stock dividends or stock splits, you must reduce the basis of your original stock. You must also reduce your basis when you receive nondividend distributions (discussed in chapter 1). These distributions, up to the amount of your basis, are a nontaxable return of capital.

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Tell your broker or other agent the particular stock to be sold or transferred at the time of the sale or transfer, and
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Receive a written confirmation of this from your broker or other agent within a reasonable time.
Stock identified this way is the stock sold or transferred even if stock certificates from a different lot are delivered to the broker or other agent.
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Tell your broker or other agent the particular stock to be sold or transferred when you deliver the certificate to your broker or other agent, and
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Receive a written confirmation of this from your broker or other agent within a reasonable time.
Example.
You bought 100 shares of stock of XYZ Corporation in 1994 for $10 a share. In January 1995 you bought another 200 shares for $11 a share. In July 1995 you gave your son 50 shares. In December 1997 you bought 100 shares for $9 a share. In April 2007 you sold 130 shares. You cannot identify the shares you disposed of, so you must use the stock you acquired first to figure the basis. The shares of stock you gave your son had a basis of $500 (50 × $10). You figure the basis of the 130 shares of stock you sold in 2007 as follows:
| 50 shares (50 × $10) balance of stock bought in 1994 | $ 500 |
| 80 shares (80 × $11) stock bought in January 1995 | 880 |
| Total basis of stock sold in 2007 | $1,380 |







