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One Hub, Six Sale Types

Capital Gains Tax Planning

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. Pick the sale below and the matching page covers your exact situation. Or send us the details and a CPA routes it for you.

Modeled before you sign or file
CPA-routed to your exact sale type

The Short Answer

  • 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.

Most of the capital gains work we see starts the same way: a bill that arrived bigger than expected. That is almost always fixable by the numbers being read correctly the first time — the improvements you never tracked, the exclusion that was missed, the recapture that was double-counted, the rate band each slice actually falls in.

Which Sale Are You Planning?

Six sale types, six pages. Each answers your exact situation.

Main Home or Other Real Estate

The $250,000 / $500,000 exclusion, and what happens past it. See capital gains tax on real estate sale.

Rental or Investment Property

Depreciation recapture at up to 25%, plus the gain, plus the 3.8% NIIT surtax. See capital gains tax on investment property.

Second Home or Vacation Property

Why the home-sale exclusion usually does not apply. See capital gains tax on second home.

Business or Company Sale

Asset versus stock, price allocation, and QSBS §1202. See capital gains tax on business sale.

Inherited Property

The stepped-up basis, and why the tax is often smaller than feared. See capital gains tax on inherited property.

Something Else — Stock, Crypto, or Deferral

Stock and options via IPO tax strategy. Crypto sales via cryptocurrency tax services. Foreign seller? See FIRPTA withholding.

How Capital Gains Tax Planning Works

01

Model the gain — the number that decides everything

Sale price, adjusted basis, and the improvements and costs most owners undercount. Basis reconstruction alone often shrinks the taxable gain more than any other single move.

02

Check every exclusion and layer that applies

The home-sale exclusion ($250k/$500k), depreciation recapture (up to 25%), and the 3.8% net investment income tax for higher earners. A calculator misses these; a CPA doesn't.

03

Time it, offset it, structure it

Holding period, loss harvesting in the same year, which rate band each slice of gain falls in for 2026. For business sales, structure the deal before signing — see capital gains tax on business sale. To defer the tax entirely, deferral options have their own hub.

Why Sellers Trust Dimov Tax on Capital Gains

Most of the capital gains work we see starts the same way: a bill that arrived bigger than expected. Almost always the number comes down once the year is read properly — the exclusion applied, the basis rebuilt, the recapture calculated once instead of twice.

$1.5B+
in tax savings identified for clients
63%
of clients return year after year
70+
tax and financial services under one roof
15+ yrs
advising on capital gains across property, business, and investment sales

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.

The aim is the smallest defensible number. Not a range, not a guess — the number that survives review.

What Capital Gains Tax Planning Covers

Four moving parts that decide the bill on almost every sale. Get them all right, and the number is usually smaller than the first draft suggested:

Modeling
Sale price, adjusted basis, and the improvements and costs most owners undercount
Exclusions
Home-sale exclusion, depreciation recapture, 3.8% NIIT — each applies (or doesn't) based on how the asset was used
Timing
Holding period, loss harvesting, which 2026 rate band each slice of gain falls in
Structure
On a business or large property sale, the deal terms set the tax — and they lock early

Sources: IRS Topic 409 (capital gains rates); Publication 523 (home-sale exclusion); Publication 544 (sales and dispositions)

When to Bring in a CPA

A good fit if:

  • You're selling a main home and the gain will exceed $250k single / $500k married
  • You're selling a rental and want the recapture and 1031 modeled before you sign
  • You're selling a business and the letter of intent hasn't been signed yet
  • You've inherited property and need the stepped-up basis documented
  • You have both W-2 income and a large sale, and the NIIT surtax could apply
  • You're a foreign seller of US real estate (FIRPTA withholding)

New to the topic? Start with the sale type that matches your situation — the pages above. For a general primer, see comprehensive guide to capital gains tax or what is capital gains tax 2025. Deferral options have their own hub.

Get My Capital Gains Number

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.

"About a quarter of the clients' returns that I look at are not fully utilizing the deductions that they have available. I think that number is even more."
— George Dimov, CPA, Founder of Dimov Tax

Confidential CPA review, not a call center. Every sale type routed to the specialist page.

Reviewed by George Dimov, CPA

Founder of Dimov Tax

15+ years advising on capital gains across property, business, and investment sales.