Can I 1031 exchange stocks, crypto, gold or personal property like an RV, a boat or an aircraft?

The 2017 change limited section 1031 to real property, and securities were always excluded

Section 1031(a)(1) now reads 'real property held for productive use in a trade or business or for investment'. Public Law 115-97 substituted 'real property' for 'property', effective for exchanges completed after December 31, 2017. Before then, equipment, vehicles, aircraft and artwork could be exchanged for like-kind personal property; they no longer can.

Securities were never in. The pre-1984 statute excluded 'stocks, bonds, notes, choses in action, certificates of trust or beneficial interest, or other securities', and Reg. section 1.1031(a)-3(a)(5) today says stock, bonds, notes, other securities and partnership interests are not real property 'regardless of the classification of such property under State or local law'. That also rules out REIT shares and fund units; see syndications, funds and LLC interests.

Two holdings that look like securities are carved back in: stock in a cooperative housing corporation, and interests in a Delaware statutory trust that Rev. Rul. 2004-86 treats as interests in the trust's real estate.

Crypto, gold and vehicles are personal property, and the IRS rejected crypto swaps even under the old rules

Notice 2014-21 treats virtual currency as property for federal tax purposes. In Chief Counsel Memorandum 202124008, the IRS concluded that exchanges of bitcoin for ether, bitcoin for litecoin, or ether for litecoin completed before January 1, 2018 did not qualify as like-kind exchanges. After 2017 the question is moot: none of it is real property.

Gold, silver and coins are collectibles under section 408(m), which covers 'any metal or gem' and 'any stamp or coin'. Section 1(h) taxes long-term collectibles gain as 28-percent rate gain rather than at the 15% or 20% capital gain rates.

An RV, boat or aircraft used in a business carries depreciation, and on sale Publication 544 treats gain on section 1245 property as ordinary income up to the lesser of the depreciation allowed or the gain. A boat slip or dock, by contrast, can be real property; the regulation lists stationary wharves and docks and treats marina slips as water space over land.

Worked example: $500,000 of stock gain sold in 2027 versus 2026

Hypothetical, round figures, married filing jointly with income already above the $613,700 top of the 15% bracket; run your own numbers with your CPA. You sell long-held stock with $500,000 of gain. At 20% plus the 3.8% net investment income tax, the federal bill is about $119,000.

If the sale is in 2027 and you invest the $500,000 gain in a qualified opportunity fund within 180 days, the amended section 1400Z-2 defers it until the earlier of selling the fund interest or five years after the investment, with a 10% basis increase at five years (30% for a qualified rural fund). That moves the tax to about 2032 and trims the gain included by a tenth.

If the sale is in 2026, a fund investment under the original rules defers the gain only to December 31, 2026, so it buys almost no time. The fund's own long-hold benefit is separate; see the rolling five-year deferral.

Installment sales and charitable remainder trusts fit some assets but not others

An installment sale spreads gain over the years payments arrive, but section 453(k) denies that treatment for installment obligations arising from sales of 'stock or securities which are traded on an established securities market'. It can work for a privately held business interest, a plane or a collection sold to a buyer who pays over time. The comparison with an exchange is in 1031 versus installment sale.

A charitable remainder trust under section 664 is not subject to income tax itself, so it can sell contributed appreciated assets without immediate tax and pay you an annuity or unitrust amount, with the remainder going to charity. The payout is taxable to you as it comes out, and the gift is irrevocable; see charitable remainder trust versus 1031.

Buying a DST with stock proceeds is a purchase, not an exchange

Proceeds from selling stock, crypto or gold can buy real estate, including a Delaware statutory trust interest, but there is no deferral because nothing like-kind was given up. The purchase does start a new real estate basis that can be exchanged later. How that works is in buying a DST without a 1031, and the full list of excluded assets is in what does not qualify.