Rental property tax tools

Keep the rental, or sell and invest the check — which one actually wins?

Two paths from today, run side by side: sell now and invest the after-tax check at your alternative return, or keep the rental — collecting rent, paying down the mortgage, and banking the depreciation shelter — then sell in whichever year you choose. The sell side of every year is computed by the exact code that runs the live calculator.

100% free Nothing leaves your browser Sale side: sale engine v1.3.0, verbatim

Keep vs. Sell

Start from a scenario below, or plug in your own numbers — every field is shared with the sale calculator.

Start from a scenario

Property & sale shared with the sale calculator

The keep side the four engines

The comparison

What you'd earn on money outside the rental — index funds, T-bills, your call. Both paths invest their spare cash at this rate.

Keep, then sell in that year Sell now, invest the check Crossover
Year by year

How this is calculated

Each year the keep path collects rent (minus vacancy), pays operating costs, maintenance, and the mortgage, and pays tax at your marginal rate on the taxable slice (rent − costs − mortgage interest − depreciation, with losses carried forward). Whatever's left — positive or negative — flows into a side fund earning the alternative return. The keep line at year Y is that year's after-tax sale check (computed by the live calculator's engine) plus the side fund. The sell line is today's after-tax check compounding at the alternative return.

Simplifications, on purpose: investment taxation is a single annual drag on returns (both paths) rather than full basis tracking; marginal rate is a single input, not bracket-computed (the loss release at sale can straddle brackets); loss release assumes a fully taxable sale to an unrelated party; the $25k active-participation allowance (below ~$150k MAGI) is not modeled, which slightly understates the keep side for moderate incomes. State rates are editable effective-rate estimates; local add-ons and resident-state credits are not included.
This is a planning estimate, not tax advice. Recapture, NIIT, suspended-loss rules, and state credits have edge cases and change over time — verify the numbers with a CPA before acting on a sale.

The two numbers this comparison puts side by side

Keeping a rental earns four ways at once — cash flow, principal paydown, appreciation, and the depreciation tax shelter — and almost nobody adds all four up. Selling frees a single number: the after-tax check, once selling costs, depreciation recapture, capital gains, the 3.8% NIIT, and state tax all come out. This tool runs both forward year by year so you can see which one actually wins for your numbers, not a rule of thumb.

The keep line each year is that year's after-tax sale check — computed by the exact sale engine that runs the live calculator — plus a side fund built from every year's net-of-tax cash flow, reinvested at your alternative return. The sell line is simply today's check compounding at that same rate. Where the lines cross (if they do) is the year the rental "pays for itself" against your alternative.

Full framework, plain English

This tool is the calculator; Should I sell my rental property? is the reasoning behind it — the four engines of keeping, why the after-tax check (not your equity) is the honest opportunity cost of selling, and the tiebreakers (Section 121, 1031, step-up at death) that can override the math entirely.

Read the framework →

Keep-vs-sell questions, answered

How does the keep-vs-sell comparison work?

It compares two paths from today: selling now and investing the after-tax check at your alternative return, versus keeping the rental — collecting rent, paying operating costs and the mortgage, and banking the depreciation tax shelter — then selling in whichever year you choose. The keep path's value in a given year is that year's after-tax sale check (computed by the same engine as the live calculator) plus the side fund built from every year's net cash flow.

What is the "crossover year"?

The year one path overtakes the other, if it does. Some scenarios never cross — one path leads the whole horizon — and some genuinely flip, usually because a cheap locked-in mortgage or a suspended-loss release changes which path compounds faster.

What does the tax drag input do?

It's an optional annual haircut applied to the alternative return on both paths, for modeling a taxable brokerage account instead of a tax-advantaged one. Leave it at 0 if you're already entering an after-tax alternative return.

What isn't this tool modeling?

The marginal tax rate on rental income is a single input rather than bracket-computed, suspended passive losses are assumed fully deductible at a taxable sale to an unrelated party, the $25,000 active-participation loss allowance isn't modeled, and side-fund growth uses a flat tax-drag input rather than full basis tracking. See "How this is calculated" above the FAQ for the complete list.

Is this tax advice?

No. It's a planning estimate to help you compare two paths before talking to a professional. Confirm any number that matters with a licensed CPA before acting on a sale.