TCP Area IV: Property Transactions

Basis, realized vs recognized gain/loss, capital vs ordinary character, depreciation recapture, §1231 netting, and nonrecognition transactions

Basis of property §1012 / §1014 / §1015

Basis is the taxpayer's investment in property for tax purposes. It is the starting point for measuring gain or loss on a later disposition, and it drives depreciation deductions. How basis is determined depends on how the property was acquired: by purchase, by gift, or by inheritance.

Cost basis (§1012)

Property acquired by purchase takes a cost basis equal to the cash paid plus the FMV of any property given up plus liabilities assumed or taken subject to. Cost basis also includes acquisition costs that are capitalized, such as sales tax, freight, installation, legal fees, title insurance, and recording fees.

Basis adjustments

After acquisition, basis is adjusted up and down over the holding period to arrive at adjusted basis:

Adjusted basis = original basis + improvements − accumulated depreciation (and other downward adjustments).

Gifted property: the dual-basis rule (§1015)

The donee generally takes the donor's basis (carryover or "transferred" basis), but a special rule prevents shifting a built-in loss to the donee. The basis used depends on the FMV at the date of the gift and on the later selling price:

The dual-basis (loss) limitation applies only when FMV at the date of gift is below the donor's basis. If FMV equals or exceeds the donor's basis at the gift date, the carryover basis is used for both gain and loss.

Holding period for gifts

When the donee uses the donor's carryover basis (the gain basis), the donor's holding period tacks on (carries over). When the donee is forced to use FMV at the date of gift (the loss basis), the holding period begins on the date of the gift.

Gift tax paid on appreciation

If the donor paid gift tax, the donee adds to basis the portion of the gift tax attributable to the net appreciation in the property. The add-on is computed as:

Gift tax paid × (net appreciation ÷ taxable gift), where net appreciation = FMV at gift date − donor's adjusted basis.

Inherited property (§1014)

Property acquired from a decedent takes a basis equal to its FMV at the date of death, giving the heir a "step-up" (or step-down) to FMV. If the executor elects the alternate valuation date (AVD), basis is FMV six months after death (or the date of disposition if sold earlier). The AVD election is available only if it reduces both the gross estate and the estate tax.

Inherited property automatically receives long-term holding period treatment regardless of how long the heir actually holds it.

GIFT basis: "Lower for Loss" Donee uses the Lower of carryover basis or FMV only when computing a Loss. Sell high, use carryover (gain basis); sell low (below FMV), use FMV (loss basis); sell in between, no gain and no loss.
Worked dual-basis example. Donor's adjusted basis is $10,000; FMV at gift date is $7,000 (built-in loss, so the dual-basis rule applies). Gain basis = $10,000; loss basis = $7,000.
  • Donee sells for $12,000: gain = $12,000 − $10,000 = $2,000 gain.
  • Donee sells for $5,000: loss = $5,000 − $7,000 = $2,000 loss.
  • Donee sells for $8,500 (between $7,000 and $10,000): no gain and no loss.

Amount realized, gain/loss & holding period §1001 / §1222 / §1223

A disposition produces a realized gain or loss, but only the recognized portion is reported on the return. The character (capital vs ordinary, short-term vs long-term) then flows into the netting process.

Amount realized (§1001)

The amount realized on a sale or exchange equals everything the seller receives:

Realized vs recognized

Realized gain or loss = amount realized − adjusted basis. Recognized gain or loss is the amount actually included in taxable income. The two are equal unless a nonrecognition provision (such as §1031, §1033, §121, §267, or §1091) defers or disallows part of the result.

Holding period (§1222)

The holding period determines whether a capital gain or loss is short-term or long-term:

The holding period begins the day after acquisition and includes the date of disposition.

Tacking of holding periods (§1223)

In several situations the prior owner's (or prior property's) holding period carries over, or "tacks":

Netting overview

Once each disposition is classified by character and holding period, short-term items net against short-term and long-term against long-term, and the net results are then combined. The detailed steps appear in the next card.

Realized vs Recognized Realized is the math (amount realized − adjusted basis). Recognized is what hits the return. They match unless a nonrecognition rule steps in to defer or disallow.
Trap. Relief from a liability is part of the amount realized to the seller, even though no cash changes hands. A taxpayer who sells property and is relieved of a mortgage can recognize gain with little or no cash in pocket ("phantom gain").

Capital gains & losses; netting §1(h) / §1211 / §1212

Capital assets receive preferential rates on net long-term gains, but capital losses are limited. Knowing what is (and is not) a capital asset is the first step.

Capital asset definition and exclusions

A capital asset is any property held by the taxpayer except the statutory exclusions. The common exclusions (which produce ordinary income or §1231 treatment) are:

Preferential long-term rates (§1(h))

Net long-term capital gain of individuals is taxed at preferential rates that depend on the taxpayer's bracket:

The netting process

Capital gains and losses are netted within each holding-period group first, then combined:

  1. Net all short-term gains and losses into a net short-term position.
  2. Net all long-term gains and losses into a net long-term position.
  3. If one is a gain and the other a loss, net them against each other; the surviving character controls.
  4. A net long-term gain that survives is taxed at the preferential rates; a net short-term gain is taxed at ordinary rates.

Capital loss limitations (§1211 / §1212)

 IndividualsC corporations
Deduction against ordinary incomeUp to $3,000 per year ($1,500 MFS)None; losses offset capital gains only
CarryoverIndefinite carryforward (retains character)Back 3 years, forward 5 years (all short-term)

§1244 small business stock

A loss on qualifying §1244 stock is treated as an ordinary loss up to $50,000 per year ($100,000 MFJ); any excess loss is capital. Gains on §1244 stock remain capital.

§1202 qualified small business stock (QSBS)

Noncorporate taxpayers may exclude a percentage (50%, 75%, or 100% depending on acquisition date) of gain on QSBS held more than five years, subject to a per-issuer cap of the greater of $10 million or 10 times basis.

Netting steps: "Net Short, Net Long, then Combine" Short with short, Long with long, then offset the two. Surviving character (LT vs ST) sets the rate. Individuals: $3,000 against ordinary, carry the rest forever.
Trap. Corporations get no preferential capital gains rate and cannot deduct net capital losses against ordinary income. A corporate capital loss is only useful if the corporation has (or will have within the 3-back/5-forward window) capital gains to absorb it.

§1231 assets & the netting process §1231

§1231 governs property used in a trade or business and gives taxpayers the best of both worlds: net gains are capital, net losses are ordinary.

What is a §1231 asset?

§1231 assets are depreciable personal property and real property used in a trade or business and held more than one year (> 1 year). It also covers certain involuntary conversions of business and investment property. Inventory, property held for sale to customers, and property held one year or less are excluded.

The "best of both" result

Five-year lookback recapture

To prevent taxpayers from bunching losses in one year (ordinary benefit) and gains in another (capital benefit), a net §1231 gain is recharacterized as ordinary income to the extent of "nonrecaptured" net §1231 losses deducted in the five preceding tax years. Only the excess over those prior losses gets long-term capital gain treatment.

Interaction with casualty gains and losses

Casualty and theft gains and losses on business and investment property are first netted separately in a preliminary step:

§1231: "Win the gain, win the loss" Net gain → long-term capital (low rate). Net loss → ordinary (full deduction). The catch is the five-year lookback that turns gains back into ordinary income to the extent of recent §1231 losses.
Five-year lookback trap. A current-year net §1231 gain is ordinary income up to the total of net §1231 losses claimed in the prior five years that have not already been recaptured. Example: $40,000 net §1231 gain this year, with $15,000 of unrecaptured §1231 losses from the prior five years → $15,000 is ordinary income and only $25,000 is long-term capital gain.

Depreciation recapture §1245 / §1250

Recapture converts part of a §1231 gain back into ordinary income because depreciation previously reduced ordinary income. Recapture applies only to gains, never to losses, and never creates additional gain.

§1245 recapture (personal property)

For depreciable personal property (machinery, equipment, furniture), §1245 recaptures as ordinary income the lesser of:

Any remaining gain beyond the recapture amount is §1231 gain (potential long-term capital gain). Because most equipment sells for less than original cost, the entire gain is often ordinary recapture.

§1250 recapture (real property)

For depreciable real property, §1250 recaptures as ordinary income only the "additional" depreciation, meaning depreciation taken in excess of straight-line. Because MACRS requires straight-line for real property placed in service after 1986, §1250 recapture is usually $0.

However, the straight-line depreciation portion of the gain is unrecaptured §1250 gain, taxed at a maximum 25% rate for individuals (it is still §1231/capital in character, just rate-capped).

Corporate §291 adjustment

For C corporations selling §1250 property, §291 converts an additional amount to ordinary income: 20% of the excess of (the amount that would be ordinary if the property were §1245) over (the amount actually treated as ordinary under §1250). This effectively makes 20% of the would-be §1245 recapture ordinary for corporations.

Feature§1245 (personal property)§1250 (real property)
Applies toDepreciable personal property (equipment, machinery)Depreciable real property (buildings)
Amount recaptured as ordinaryLesser of gain or all depreciation takenOnly "additional" (accelerated over straight-line) depreciation
Typical result under MACRSMost or all gain is ordinaryUsually $0 (straight-line realty)
Rate cap on remainderExcess is §1231 gainStraight-line portion is unrecaptured §1250 gain, taxed at max 25%
Corporate add-onNone§291: 20% of would-be §1245 recapture is ordinary
§1245: "Lesser of gain or depreciation" Recapture the smaller of the gain or the total depreciation as ordinary; the rest is §1231. For realty (§1250), straight-line MACRS means little or no recapture, but the depreciation portion is rate-capped at 25% for individuals.
Trap. Recapture never applies to a loss and never exceeds the realized gain. If a depreciable asset is sold at a loss, there is no §1245 or §1250 recapture; the loss is simply a §1231 loss (ordinary if it survives netting).

Like-kind exchanges & involuntary conversions §1031 / §1033

These provisions defer gain (and loss, for §1031) when property is exchanged for similar property or replaced after an involuntary loss, so that the taxpayer's investment continues without a cash-out event.

§1031 like-kind exchanges

Post-TCJA, §1031 applies only to real property held for productive use in a trade or business or for investment. Personal property (equipment, vehicles, intangibles) no longer qualifies. Real property is broadly "like-kind" to other real property (improved for unimproved, land for a building).

Boot

Boot is non-like-kind property received (cash, other property, or net liability relief). When boot is received, recognized gain = the lesser of realized gain or boot received. Loss is never recognized on a §1031 exchange, even if boot is received.

Basis in replacement property

Two equivalent ways to compute the substituted basis of the replacement real property:

The holding period of the relinquished property tacks to the replacement property.

Related-party two-year rule

If like-kind property is exchanged between related parties, both parties must hold their replacement property for at least two years. If either disposes of it within two years, the originally deferred gain is triggered (recognized).

§1033 involuntary conversions

When property is involuntarily converted (casualty, theft, condemnation), gain may be deferred (elective) if the taxpayer reinvests the proceeds in qualifying replacement property within the replacement period:

Replacement property must meet a qualifying-use (functional-use or, for condemned realty, like-kind) test. Gain is recognized to the extent proceeds are not reinvested. Unlike §1031, §1033 deferral is elective and direct exchange is not required.

Boot: "Recognize the lesser" Recognized gain in a §1031 exchange = lesser of realized gain or boot received. No boot, no gain. Losses are never recognized in §1031, even with boot.
Trap. §1031 no longer applies to equipment, vehicles, or any personal/intangible property after the TCJA. An exchange of business machinery is a fully taxable sale and purchase, with depreciation recapture in the year of sale. Only real property qualifies for like-kind deferral.

Other nonrecognition & loss-disallowance rules §121 / §267 / §1091

Beyond exchanges, several rules either exclude gain on personal-use property or disallow losses in suspect situations.

§121 home-sale exclusion

An individual may exclude gain on the sale of a principal residence:

A loss on a personal residence is never deductible.

§267 related-party loss disallowance

Losses on sales between related parties (family members, and an individual and a more-than-50%-owned entity) are disallowed to the seller. Related parties for this rule include spouses, siblings, ancestors, and lineal descendants (but not in-laws).

When the related buyer later sells to an unrelated third party, the buyer may use the previously disallowed loss to offset any gain on that later sale (the "right of offset"). The offset cannot create or increase a loss for the buyer; any unused disallowed loss simply disappears.

§1091 wash-sale rule

A loss on the sale of stock or securities is disallowed if the taxpayer buys substantially identical securities within 30 days before or after the sale (a 61-day window). The disallowed loss is added to the basis of the replacement securities, preserving it for the future, and the holding period tacks. The wash-sale rule applies only to losses, not gains.

§1041 transfers between spouses

Transfers of property between spouses (or incident to divorce) are nonrecognition events: no gain or loss is recognized, and the transferee takes a carryover basis (treated as a gift for basis purposes, including the donor's holding period).

Disallowed losses: "RAW" Related party (§267), And Wash sale (§1091). Both defeat a loss deduction; §267 may give the related buyer a right of offset, and §1091 adds the loss to the replacement security's basis.
Wash-sale window trap. The 30-day period runs both directions, so the danger zone is a full 61 days (30 days before the sale, the sale date, and 30 days after). Buying back a "substantially identical" security anywhere in that window disallows the loss; it is not eliminated but rolled into the basis of the replacement shares.

Installment sales & planning §453

The installment method lets a seller report gain as cash is collected rather than all in the year of sale, smoothing income and deferring tax. It is the default method for an eligible sale with at least one payment received after the year of sale.

How the installment method works

Each principal collection carries out gain at the gross profit percentage:

Interest stated (or imputed) on the deferred payments is reported separately as ordinary interest income.

Ineligible items

The installment method may not be used for:

Interest on deferred tax (large obligations)

For large installment obligations, the seller may owe interest on the deferred tax liability. This applies to nondealer obligations when the face amount of all such obligations outstanding at year-end exceeds $5 million, and to certain dealer-related rules. It is a cost of deferral the planner must weigh.

Planning considerations

Installment gain: "GP% times cash" Gross profit percentage (gross profit ÷ contract price) applied to each principal collection gives the gain to report that year. Interest is reported separately. Recapture and inventory do not get to ride along.
Recapture trap. §1245 and §1250 depreciation recapture is fully recognized as ordinary income in the year of sale, regardless of how little cash is collected that year. The recapture also increases the basis used in the installment computation, so only the remaining gain is spread across the collection years.