Hawaii taxes capital gains as ordinary income (7.25%), on top of federal capital gains tax and the 3.8% NIIT. Spreading the gain across years is how you keep more of it.
Hawaii taxes capital gains as ordinary income but caps the rate at 7.25%. Stacked on the federal rate (up to 20%) and the 3.8% Net Investment Income Tax, a one-year sale of a business, building, or appreciated asset takes a serious bite.
Send me the sale price and rough basis. Within one business day I'll email you the actual number and the Seller's Guide to §453. If it doesn't fit your deal, I'll tell you that plainly.
No retainer · no obligation. Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
The federal tax, the 3.8% surtax, and your Hawaii tax are all driven by recognizing the gain in a single year. A §453 structured installment sale lets you receive the proceeds (and pay the tax) over future years, keeping more of the gain in lower brackets, reducing the surtax, and lowering the Hawaii tax in the deferred years. Payments come from an assignment company funded by a fixed annuity from a highly rated life insurer, and because it's a federal statute it works fully in Hawaii. Unlike a 1031, no replacement property is required.
Estimate your number on the calculator (select Hawaii), then plan the structure before you sign.
Hawaii taxes capital gains as ordinary income, at a maximum 7.25%. This is on top of the federal rate (up to 20%) and the 3.8% NIIT.
Yes. A §453 structured installment sale spreads the proceeds and gain over multiple years, lowering the federal and Hawaii tax in the deferred years. It's a federal strategy that works in Hawaii.
A 1031 works for like-kind real estate if you reinvest on schedule. A structured installment sale fits if you want to exit real estate, are selling a business or stock, or can't find a replacement property.
Yes. Recapture on equipment and other §1245 property is taxed in the year of sale even in an installment sale. Unrecaptured §1250 gain on a building (taxed at up to 25%) and the capital gain are spread with the payments.
Use the free capital gains tax calculator, select Hawaii, and it estimates federal + state + NIIT + recapture, then shows the savings from deferring.
Before you sign anything, run your numbers with someone who structures the deal to be tax-smart and audit-ready from day one.
Call 213-414-2808 Run the Numbers →
A plain-English guide for sellers on how a structured installment sale defers the tax when you sell a business, practice, or property. It covers the math, the alternatives, and how to tell if your deal fits.
Leave your details and the PDF downloads right away. Within one business day Hans will email a preliminary read on which structure fits your deal. No retainer. On a funded structure, the insurer pays a one-time commission of about 4% of the amount structured to the brokerage firm that places it (Hans’s share is about 2.4%; no trail). It is built into the annuity pricing, not a separate fee.
📞 Hans Goldstein · 213-414-2808 · CA Insurance License #4273294 · Independent §453 specialist · Goldstein & Co. LLC
Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
