Selling an investment property creates two separate tax events that trip up a lot of property owners. The first is capital gains tax on your profit. The second is depreciation recapture on the tax deductions you took while owning the property.

Capital gains tax applies to the difference between your selling price and your adjusted cost basis. If you held the property for more than a year, you’ll pay long-term capital gains rates of 0%, 15%, or 20% depending on your income. Properties held less than a year get taxed at your ordinary income rate, which can be significantly higher.

Depreciation recapture is where people get surprised. When you own a rental property, you deduct depreciation each year to offset your rental income. The IRS requires you to depreciate residential rental property over 27.5 years whether you claim the deduction or not. When you sell, you owe tax on that accumulated depreciation at a flat 25% rate. If you owned the property for ten years and depreciated $80,000, that’s $20,000 in depreciation recapture tax alone.

High earners also face the Net Investment Income Tax. If your modified adjusted gross income exceeds $200,000 as a single filer or $250,000 married filing jointly, you’ll pay an additional 3.8% on your investment gains. Real estate investors with multiple properties or other investment income often hit this threshold in the year they sell.

Massachusetts adds its own layer. The state taxes long-term capital gains at 5% and short-term gains at 12%. Combined with federal taxes, your total effective rate on a property sale can easily reach 30% or higher.

A 1031 exchange lets you defer these taxes by reinvesting the proceeds into another investment property. The rules are strict. You have 45 days to identify replacement properties and 180 days to close. You need a qualified intermediary to hold the funds. Miss the deadlines or touch the money yourself and the deferral fails.

Your cost basis matters for calculating everything. Start with your purchase price, add closing costs from when you bought, add capital improvements you made over the years, then subtract accumulated depreciation. The difference between your net selling price and this adjusted basis is your taxable gain.

Track your improvements carefully. A new roof, HVAC replacement, or kitchen renovation increases your basis and reduces your taxable gain. Repairs that you expensed in the year they happened don’t count. The distinction between improvements and repairs makes a real difference at sale time.

Work with a CPA before you sell, not after. Timing the sale across tax years, installment sales, and opportunity zone investments are all strategies that require planning. A Merrimack Valley bookkeeper can help you organize records and calculate your adjusted basis, but the tax planning itself needs someone who specializes in real estate taxation.