Published on Jan 28, 2026 • Updated on Jun 18, 2026
This article was written by Salvatore M. Capizzi
Salvatore M. Capizzi, CEPA, CBDA, is Dunham's Chief of Sales & Marketing and a 2026 Wealthies CMO of the Year Finalist. His work focuses on retirement planning, emerging trends for financial advisors, and advanced tax, trust, and estate strategies.
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If your client or prospect is selling a highly appreciated business or real estate, it can provide them with a wonderful and satisfying experience. They are seeing the seeds they planted grow into the valuable enterprise that it is today.
Our experience tells us that considering a planning tool known as an Intermediated Installment Sale could provide a number of overlooked benefits, which could be helpful while selling highly appreciated assets.
An Intermediated Installment Sale is an alternative to an outright sale which uses IRS Code §453 as its foundation. Known as an Installment Sale, it provides a number of benefits when compared to an outright sale.
At its core, an Intermediated Installment Sale spreads the income from the sale over the life of the installment note. In some circumstances, spreading the capital gains over multiple years can provide financial benefits compared to reporting the entire gain in one year.
Step-by-step overview:
Let us explore a hypothetical case study and assume the following:
- Federal tax rate of 20%.
- State effective tax rate of 12.93%.
- Medicare tax rate of 3.8%.[1]
*Note that there may be other state or local sale or transfer taxes that apply at the time of sale; these are not itemized here for purposes of this hypothetical example.
Based on our hypothetical case study, if you sell the business outright for $5 million and your cost basis is $500,000, your taxable gain is $4.5 million. Therefore, at sale, estimated capital gains taxes due will be:
Thus, instead of an outright sale, you can sell the asset in a carefully constructed Intermediated Installment Sale. Since you defer taxes in the Intermediated Installment Sale, you would begin with the full $5 million invested as opposed to the after-tax amount of $3,347,333 in the outright sale.
The money in the trust from the completion of the Intermediated Installment Sale allows the trust to enjoy the "earning power" of the $1,652,567 that would have been immediately paid in taxes under the outright sale.
This can potentially provide more investable cash and more income.
Below is a hypothetical illustration comparing an Intermediated Installment Sale to an outright sale of the asset. In the calculations, we assume a sale price of $5,000,000 with a cost basis of $500,000, as per the above hypothetical case study.
This illustration assumes the same post sales income tax on the investment income and same advisory fees but provides the net return on the trust after trust administration fees. We are assuming a 10-year note with an option taken for an additional five years for a total of 15 years. We are assuming this note is interest only with a balloon at the end of the 15 years, at which point, the tax on the sale of the asset is due.
In this hypothetical case study, the Intermediated Installment Sales potentially provides a total of $1,228,091 of additional income and economic value during the 15-year period.
In addition, if we assume a 2% rate of inflation, the present value of the tax due today of $1,652,850 paid 15 years from now, would be $1,228,091 or 74.3 cents on the dollar, thereby putting inflation to work for your client!
In our view, the Intermediated Installment Sale provides significant advantages to an outright sale – advantages many times over looked when transitioning ownership of a business or real estate.
At the same time, it creates a large pool of assets for you to manage.
An Intermediated Installment Sale can help clients defer capital gains taxes for up to 20 years, preserve investable capital, and benefit from inflation — while giving financial advisors the opportunity to manage significantly larger asset pools.
Also, please feel free to forward this to other financial advisors you feel may benefit from this strategy.
What is an intermediated installment sale? An intermediated installment sale is a tax deferral strategy built on IRC §453 that allows the seller of a highly appreciated asset to defer capital gains taxes for up to 20 years. Instead of selling directly to a buyer, the asset is sold through an independent trust, which purchases it from the seller via a promissory note and then sells it to the end buyer under the original terms.
How long can you defer capital gains taxes on a business sale? Under an intermediated installment sale structured on IRC §453, capital gains taxes can be deferred for up to 20 years. A typical structure uses a 10-year note with an option to extend for an additional five years, with taxes on the full gain due at the end of the note term rather than at the time of sale.
What is the difference between an installment sale and an outright sale? In an outright sale, capital gains taxes are due immediately — at the federal rate of up to 20%, plus the 3.8% Medicare surtax for high earners, plus applicable state taxes — reducing investable capital from day one. In an installment sale, the full proceeds remain inside the trust structure, allowing returns to compound on capital that would otherwise have gone to the IRS. In a hypothetical $5 million California sale with a $500,000 cost basis, the deferred structure generates over $1.2 million in additional income and economic value over 15 years compared to an outright sale.
What are the risks of carrying a buyer note in a business sale? When a seller carries a note directly for a buyer, they absorb the buyer's credit risk — if the buyer defaults, the seller may not recover the full amount owed. An intermediated installment sale eliminates this risk by inserting an independent trust between the seller and the buyer, so the seller's promissory note is with the trust rather than the end buyer directly.
How does an installment sale help financial advisors? An intermediated installment sale keeps assets under management rather than triggering an immediate taxable distribution. Instead of managing the after-tax proceeds of a sale, the financial advisor has the opportunity to manage the full pre-tax proceeds inside the trust structure — which in a $5 million sale example represents over $1.6 million in additional investable assets compared to an outright sale.
[1] The Medicare tax may not be applicable depending on the sale structure. For this illustration, it is included.
[2] Net return on the Intermediated Instalment sales is 6% due to trust’s 50 bps annual administration fee.
This communication is general in nature and provided for educational and informational purposes only. It should not be considered or relied upon as legal, tax or investment advice or an investment recommendation, or as a substitute for legal or tax counsel. Any examples are hypothetical and are for illustrative purposes only.
Information contained in the materials included is believed to be from reliable sources, but no representations or guarantees are made as to the accuracy or completeness of information.
IRS Circular 230 Disclosure: To ensure compliance with requirements imposed by the IRS, we inform you that any U.S. federal tax advice contained in this communication (including any attachments) is not intended or written to be used, and cannot be used, for the purpose of (i) avoiding penalties under the Internal revenue Code or (ii) promoting, marketing or recommending to another party any transaction or matter addressed herein.
Dunham & Associates Investment Counsel, Inc. is a Registered Investment Adviser and Broker/Dealer. Member FINRA / SIPC. Advisory services and securities offered through Dunham & Associates Investment Counsel, Inc.
