A structured installment sale is a tax-planning strategy that lets the seller of a highly appreciated asset — a business, commercial property, or other qualifying asset — spread their capital gains over several years instead of paying the entire tax bill in the year of sale. It works under IRC §453: rather than taking a lump sum, the buyer's payment obligation is assigned to a third-party company funded by an annuity from a regulated life insurer, which then pays the seller on a fixed schedule. Because the seller only receives — and is taxed on — each payment as it arrives, the gain is recognized gradually. That keeps more of it in lower tax brackets, softens exposure to the 3.8% net investment income tax, and provides a predictable, insurer-backed income stream. For the buyer, almost nothing changes: they still pay full price in cash at close. The deferral happens entirely on the seller's side, so there's no seller note to carry and no payments to manage. The edge is strategic — if a buyer knows the seller is worried about a big capital gains hit, they can make a smarter offer. Since the tax savings can matter more to the seller than a higher price, the buyer can win the deal or bridge a valuation gap without spending an extra dollar at closing. In short * Keeps more of the gain in lower tax brackets, avoiding the spike into the top rate that a lump sum can trigger. * Reduces exposure to the 3.8% net investment income tax by lowering taxable income in any single year. * Flexible scheduling — the seller can choose when payments start (immediate or deferred) and over how many years. * A negotiating edge — knowing the seller wants to ease a big capital gains hit, the buyer can craft a smarter offer, bridge a valuation gap, or win the deal without spending an extra dollar. This strategy largely benefits sellers, but what benefits sellers can be used by smart buyers! I'm happy to answer any questions in the comments