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Capital Gains Tax Planning

TL;DR

  • Capital gains tax depends on what you sold: a main home, a rental, a second home, a business, or stock each follow different rules and rates.
  • A CPA models the actual number before you sign or file: the gain, the exclusions and recapture that apply, and the rate on each slice.
  • Pick your sale below and the matching page covers your exact situation. If you want the tax deferred instead, the deferral options have their own hub.

Capital gains tax planning starts with one question: what did you sell? The rules for a main home, a rental, a second home, a business, and inherited property differ enough that a single generic answer is usually a wrong one. Pick the page that matches your sale, or send us the details and a CPA routes it for you.

Which sale are you planning?

Main home or other real estate

the $250,000 / $500,000 exclusion, and what happens past it.

Rental or investment property

depreciation recapture at up to 25 percent, plus the gain.

Second home or vacation property

why the home-sale exclusion usually does not apply.

Business or company sale

asset versus stock, price allocation, and QSBS.

Inherited property

the stepped-up basis, and why the tax is often smaller than feared.

Any other property or asset

how the gain and the 0, 15, or 20 percent rate are figured.

Defer the tax instead

1031 exchanges, deferred sales trusts, installment sales, and GRATs compared.

Stock and options

IPO and equity comp planning.

Crypto

gains on sales and swaps, figured and reported by a CPA.

Expatriating? The US exit tax treats leaving as a deemed sale of appreciated assets: /u-s-exit-tax.

What capital gains tax planning covers

Modeling the gain

sale price, adjusted basis, and the improvements and costs most owners undercount.

Checking every exclusion and layer

the home-sale exclusion, depreciation recapture, and the 3.8 percent net investment income tax.

Timing and offsets

holding period, loss harvesting in the same year, and which rate band each slice of gain falls in for 2026.

Structure before signing

on a business or large property sale, the deal terms set the tax, and they lock early.

Most of the capital gains work we see starts the same way: a bill that arrived bigger than expected.

What capital gains tax planning costs

The fee is based on the sale. A single clean sale with good records prices low; multiple properties, a business deal, rebuilt basis, or more than one state add work, and the fee reflects that and nothing else.

To get a quote, send what you sold and what records you have; the fee comes back in writing before any work begins.

Capital Gains Tax Planning

Send the sale, the rough numbers, and how the asset was used, and a CPA either answers it directly or routes you to the specialist page that does. The aim is the smallest defensible number.