Insight

How You Can Reduce Capital Gains Taxes with a Two-Year Sale Strategy

How You Can Reduce Capital Gains Taxes with a Two-Year Sale Strategy

John M. Goralka

John M. Goralka

May 16, 2022 07:49 PM

You can also save money on net investment income taxes.

by: John M. Goralka

September 28, 2017

If you plan to sell a substantially appreciated asset, property or business, you can save money with what's called a two-year installment sale. Basically, it's a double-sale strategy to create a taxation timing gap between when the asset sale proceeds are received and when they're taxed.

Here's how it works: You can sell the asset to your children or to a separate trust (sometimes referred to as a "deferred sale trust") on a long-term installment sale. That way, your children or other beneficiaries can receive the full value and enjoyment of the property before the gain is recognized and subject to taxation. At that point, the property can be sold to a third-party buyer for cash.

For example, let's say you own Blackacre, a parcel of land that you originally purchased for $200,000. Today it has a fair market value of $1 million. You want it to benefit your children, so you sell it to a non-grantor trust in exchange for a 10-year installment note. This non grantor trust, which is a taxable entity, receives a stepped-up basis of $1 million for the property. You receive two payments of $100,000 from the non-grantor trust and recognize a gain of $80,000 on each payment. But after the second payment is made, the trust sells the property to a third party—an unrelated taxpayer—for cash. Assuming that the value of Blackacre has increased by $100,000 between the two sale dates, the value is now $1.1 million. The non grantor trust recognizes a gain of $100,000 on the sale. Yet the family receives the entire $1.1 million of value while paying tax on only $300,000 of the $900,000 gain. Yes, the trust will continue to pay off the note over the next eight years. You recognize any gains and pay the taxes over that eight-year period. But this provides a significant timing difference. Plus, you may also be able to reduce your taxable income and pay taxes from a lower tax bracket in future years.

This strategy is beneficial because the gain is taxed at a reduced rate as a long-term capital gain instead of a short-term capital gain, which would be taxed as ordinary income. And your beneficiaries still receive all the cash proceeds in the year of the second sale. Also, this strategy provides an opportunity for a far greater overall return. If you invest the funds you might have otherwise paid in taxes in the year of the original sale, you might earn 6% or more each year on that amount.

Without this strategy, capital gains taxes on sold assets can be substantial. For example, the maximum marginal capital gains rate for a California resident is 37.1%, including both federal and state taxes, while the maximum income tax rate is around 57.1%,. So minimizing those taxes can pay off substantially.

Two-year installment sales can also be used to avoid the 3.8% net investment income tax (NIIT) because it provides a lower overall tax liability and allows owners to pay that liability over a long period of time. Do take note, however, that this alternative is not available for the sale of marketable securities, such as publicly traded stock or equities.

Unfortunately, Congress partially shut down this strategy when IRC Section 453(e) was enacted. But you can still take advantage of it if you're patient. After you sell the asset to your children or a trust, you have to wait at least two years and one day to resell it to a third party for cash and enjoy the benefits described above.

Capital gains taxes can be a huge drain on proceeds from asset sales. But if you can be patient enough to wait two years and one day, two-year installment sales can be a great strategy for reducing your tax bill.

https://www.kiplinger.com/article/taxes/t054-c032-s000-reduce-capital-gains-taxes-two-year-sale-strategy.html

Related Articles

Paying the Price in P.R.


by Best Lawyers

Isis Carballo-Irigoyen discusses discuss intergovernmental relations, opportunity zones, and why a move to Puerto Rico to ease your tax burden likely won’t be as simple as you might think.

An Interview With McConnell Valdés

Baraona Fischer & Cia on the Changes Coming to Tax Law in Chile


by Best Lawyers

Juan Manuel Baraona of the 2019 "Law Firm of the Year" award-winner for Tax Law in Chile discusses forthcoming regulations, career highlights, and his secrets to success in an interview with Best Lawyers CEO Phillip Greer.

Baraona Fischer & Cia LFOTY

Lecher Pays


by Ann E. Evanko and Katherine L. Wood

Can social change be sped up via legislation? A key provision of the recent tax-law overhaul, clearly written with #MeToo in mind, suggests it can.

Social Change Amid #MeToo

Opening Pandora's Box in Portuguese Tax Law


by Best Lawyers

Diogo Ortigão Ramos discusses Cuatrecasas' 2019 "Law Firm of the Year" award for tax law in Portugal.

Cuatrecasas Law Firm of the Year Interview

Monica Biringer and Firoz Ahmed on Canada's Changing Tax Practice


by Best Lawyers

The attorneys from Canada's 2019 "Law Firm of the Year" winning Osler, Hoskin & Harcourt look at their achievements over the past year.

Osler, Hoskin & Harcourt Interview

What Spain’s Proposed ‘Google Tax’ Means for its New Economy


by Mariano Roca López

How the Spanish Stability Program is tapping new sources of tax revenue.

Will Spain Pass the 'Google Tax?'

A Master in Defending the Accused


by Best Lawyers

The relentless pursuit of justice when everything is on the line.

Patrick A. Mullin

Tax Saving Opportunities under Puerto Rico Incentives


by Alexis R. González-Pagani

Puerto Rico offers a variety of attractive incentives packages that cover multiple industry sectors.

Tax Saving Opportunities

Q&A with Konstantin Mikhel at Vlasova Mikhel & Partners


by Best Lawyers

A Q&A with Konstantin Mikhel of Vlasova Mikhel & Partners about his experiences and the legal field in Belarus.

Konstantin Mikhel

Recent Case Law on Cross-Border Reorganizations


by Marie-Hélène Raffin

The Euro Park decision is bound to facilitate the application of the French favorable tax regime to cross border mergers and spin-offs.

Cross-Border Reorganizations

Trending Articles

Presenting The Best Lawyers in Australia™ 2025


by Best Lawyers

Best Lawyers is proud to present The Best Lawyers in Australia for 2025, marking the 17th consecutive year of Best Lawyers awards in Australia.

Australia flag over outline of country

The 2024 Best Lawyers in Spain™


by Best Lawyers

Best Lawyers is honored to announce the 16th edition of The Best Lawyers in Spain™ and the third edition of Best Lawyers: Ones to Watch in Spain™ for 2024.

Tall buildings and rushing traffic against clouds and sun in sky

Best Lawyers Expands Chilean 2024 Awards


by Best Lawyers

Best Lawyers is pleased to announce the 14th edition of The Best Lawyers in Chile™ and the inaugural edition of Best Lawyers: Ones to Watch in Chile™, honoring the top lawyers and firms conferred on by their Chilean peers.

Landscape of city in Chile

Best Lawyers Expands 2024 Brazilian Awards


by Best Lawyers

Best Lawyers is honored to announce the 14th edition of The Best Lawyers in Brazil™ and the first edition of Best Lawyers: Ones to Watch in Brazil™.

Image of Brazil city and water from sky

Announcing The Best Lawyers in South Africa™ 2024


by Best Lawyers

Best Lawyers is excited to announce the landmark 15th edition of The Best Lawyers in South Africa™ for 2024, including the exclusive "Law Firm of the Year" awards.

Sky view of South Africa town and waterways

The Best Lawyers in Mexico Celebrates a Milestone Year


by Best Lawyers

Best Lawyers is excited to announce the 15th edition of The Best Lawyers in Mexico™ and the second edition of Best Lawyers: Ones to Watch in Mexico™ for 2024.

Sky view of Mexico city scape

How Palworld Is Testing the Limits of Nintendo’s Legal Power


by Gregory Sirico

Many are calling the new game Palworld “Pokémon GO with guns,” noting the games striking similarities. Experts speculate how Nintendo could take legal action.

Animated figures with guns stand on top of creatures

The Best Lawyers in Portugal™ 2024


by Best Lawyers

The 2024 awards for Portugal include the 14th edition of The Best Lawyers in Portugal™ and 2nd edition of Best Lawyers: Ones to Watch in Portugal™.

City and beach with green water and blue sky

How To Find A Pro Bono Lawyer


by Best Lawyers

Best Lawyers dives into the vital role pro bono lawyers play in ensuring access to justice for all and the transformative impact they have on communities.

Hands joined around a table with phone, paper, pen and glasses

The Best Lawyers in Peru™ 2024


by Best Lawyers

Best Lawyers is excited to announce the landmark 10th edition of The Best Lawyers in Peru, the prestigious award recognizing the country's lop legal talent.

Landscape of Peru city with cliffside and ocean

Presenting the 2024 Best Lawyers Family Law Legal Guide


by Best Lawyers

The 2024 Best Lawyers Family Law Legal Guide is now live and includes recognitions for all Best Lawyers family law awards. Read below and explore the legal guide.

Man entering home and hugging two children in doorway

Announcing The Best Lawyers in New Zealand™ 2025 Awards


by Best Lawyers

Best Lawyers is announcing the 16th edition of The Best Lawyers in New Zealand for 2025, including individual Best Lawyers and "Lawyer of the Year" awards.

New Zealand flag over image of country outline

The Best Lawyers in Colombia™ 2024


by Best Lawyers

Best Lawyers is honored to announce the 14th edition of The Best Lawyers in Colombia™ for 2024, which honors Colombia's most esteemed lawyers and law firms.

Cityscape of Colombia with blue cloudy sky above

Announcing The Best Lawyers in Japan™ 2025


by Best Lawyers

For a milestone 15th edition, Best Lawyers is proud to announce The Best Lawyers in Japan.

Japan flag over outline of country

Announcing the 2024 Best Lawyers in Puerto Rico™


by Best Lawyers

Best Lawyers is proud to announce the 11th edition of The Best Lawyers in Puerto Rico™, honoring the top lawyers and firms across the country for 2024.

View of Puerto Rico city from the ocean

The Best Lawyers in Singapore™ 2025 Edition


by Best Lawyers

For 2025, Best Lawyers presents the most esteemed awards for lawyers and law firms in Singapore.

Singapore flag over outline of country