Big Sale TaxHans Goldstein: Tax & Exit Planning
Home / What to send
Free checklist

What to send for a sale tax analysis

The documents that matter, ranked from most important to nice to have, with the exact pages, how far back to go and where to get each one. Pick what you are selling and see only your list. Send what you have now. The more you send, the sharper the numbers.

Ranked by impactLook-back and the rule behind itWorks with no upload

What are you selling?

Showing every item. Pick what you are selling to see only your list. Download this list (PDF)

1

Send these first

Enough to start the analysis.

Federal income tax returns, complete

The whole return as filed: every schedule, statement, worksheet and the e-file confirmation, not just the first two pages.

Which pages and forms
Form 1040 with Schedules 1, 2, 3, B, C, D, E, F and A as they apply, plus Forms 8949, 4797, 4562, 8582, 6252, 8824, 8960, 8995, 6198, 6251, 7203, 1116 and the carryover worksheets and statement pages behind them.
How far back
Last 3 years minimum (the IRS normally has 3 years to assess, IRC 6501(a)). Send 5 to 7 if you can: losses and credits carry forward past 3 years (see the carryforward item).
Why it matters
It shows your bracket, your carryovers, and any earlier installment sale or exchange. Everything else is checked against it.
Do not have it? Get it here
Your CPA or tax software export. No copy? Pull return transcripts free from IRS Online Account (irs.gov/account): return transcripts for the current and three prior years; Form 4506-T for older transcripts. A transcript is a summary, so ask your CPA for the full PDF too.

State income tax returns, complete

Every state return you filed, with schedules, for each state where you live, own the property or have the business.

Which pages and forms
For example California Form 540 with Schedule CA and Schedule D (540), Form 3885A (depreciation), Form 3840 or 3805 (exchanges), Form 593 and 592-B (withholding on sales). Other states: the resident and any nonresident returns.
How far back
Same years as the federal returns, 3 minimum, 5 to 7 better. State carryovers and basis often differ from federal.
Why it matters
State tax is often the second biggest line after federal, and some states tax installment gain and exchange gain differently.
Do not have it? Get it here
Your CPA, or the state tax agency's online account (for example California FTB MyFTB) for transcripts and notices.

The sale paperwork: listing, offer or purchase agreement

The listing agreement or offering memorandum, any letter of intent, the purchase and sale agreement and every amendment, with the price allocation if there is one.

Which pages and forms
Price, deposit, closing date, contingencies, what the buyer assumes, seller-carry or note terms, repairs credits, and the allocation between land, building and equipment.
How far back
The current deal. Also any earlier offers that fell through if the terms are different.
Why it matters
The tax depends on what is actually sold, to whom, for how much and on what terms. Terms that change the tax (seller note, assumed debt, earn-out) must be seen before you sign.
Do not have it? Get it here
Your listing broker, the buyer's broker, or your title or escrow company. No contract yet? Send the listing or your asking terms.

The sale paperwork: letter of intent or purchase agreement

The letter of intent, the stock or asset purchase agreement and every draft and amendment, with the purchase price allocation schedule.

Which pages and forms
Price, cash at closing, seller note, earn-out, holdback or escrow, working capital adjustment, non-compete and consulting terms, and the allocation by class (IRS Form 8594 classes I to VII for an asset sale, IRC 1060).
How far back
The current deal and any earlier drafts with different terms.
Why it matters
Allocation and the form of the deal (stock or asset) decide how much of the price is capital gain, ordinary income or recapture.
Do not have it? Get it here
Your M&A broker or investment banker, your deal attorney, or the buyer's counsel. No LOI yet? Send the broker's valuation or your asking terms.

What you plan to sell and when

A list of the positions, coins or items you plan to sell, the approximate sale date, and a current statement showing each one.

Which pages and forms
Name, ticker or description, quantity, today's value, and whether any are pledged or held in a trust or entity.
How far back
Current statement, dated within the last 30 days.
Why it matters
Timing across two tax years, and which lots you sell, can move the bill more than anything else here.
Do not have it? Get it here
Your brokerage or custodian's online statements; exchange or wallet accounts for crypto; the dealer or auction house for collectibles.

Seller net sheet or estimated closing statement

The title company's estimate of what you walk away with: price, payoffs, commissions, transfer taxes, prorations, credits.

Which pages and forms
Gross price, loan payoffs, broker commission, escrow and title fees, transfer and documentary taxes, prorated taxes and rents, and your estimated net cash.
How far back
The latest estimate. Ask for a fresh one when the price or closing date changes.
Why it matters
It is your real cash, which is what the tax and every comparison is measured against.
Do not have it? Get it here
Your escrow officer or listing broker can produce one in a day.

Closing statement from when you bought it

The settlement statement from your purchase (Closing Disclosure, ALTA or HUD-1).

Which pages and forms
Purchase price, closing costs you can add to basis, the land and building split, any seller credits, and loan terms.
How far back
Back to the date you acquired it, however long ago. Basis is figured from that day.
Why it matters
Basis is the number that is subtracted from the price. A missing or low basis overstates the tax.
Do not have it? Get it here
Your title or escrow company from that purchase (they keep records for years); your lender's closing package; the county recorder for the deed; your CPA's files for the year you bought.

Depreciation schedule or fixed asset ledger

Every asset you depreciate, with its cost, date placed in service, method, life, prior depreciation and remaining basis.

Which pages and forms
The depreciation report your CPA keeps (often called the fixed asset schedule) plus Form 4562 for each year. Include Section 179 and bonus depreciation. Home owners: only if you rented it or used part for business.
How far back
From the date each asset was placed in service to today. Depreciation "allowed or allowable" reduces basis whether or not you claimed it (IRC 1016(a)(2)).
Why it matters
Depreciation is taxed back at up to 25% on buildings (unrecaptured Section 1250 gain, IRC 1(h)) and as ordinary income on equipment (IRC 1245), and it is due in the year of sale even on an installment sale (IRC 453(i)).
Do not have it? Get it here
your CPA or tax software, usually a tab in their workpapers. Ask for "the depreciation schedule through last year."

Every loan on it: statement, payoff quote and note

The latest statement for each loan, a payoff quote for the closing date, and the note terms.

Which pages and forms
Balance, rate, maturity, prepayment penalty or yield maintenance or defeasance, due-on-sale and assumption terms. Include HELOCs, lines of credit, seller notes owed and any loan secured by this asset, even if the money was used elsewhere.
How far back
Current. Add the original loan documents if the note has an unusual prepayment clause.
Why it matters
Debt over basis is treated as cash in some deals, a prepayment penalty comes off your net, and an old low-rate loan is often worth more than the tax saved by selling.
Do not have it? Get it here
Your lender's online portal (statement and payoff quote), or call the servicer. The county recorder lists the recorded deeds of trust.

How you own it: deed and entity documents

The vesting deed or entity documents showing who owns the asset and in what percentages.

Which pages and forms
Recorded deed (vesting language), operating agreement or partnership agreement and all amendments, trust agreement, articles, cap table or stock ledger.
How far back
Current, plus any transfer of title since you acquired it (gifts, contributions to an LLC or trust).
Why it matters
Who is the taxpayer, how many owners there are and whether the owner is an entity or a trust changes the brackets, the forms and the options.
Do not have it? Get it here
County recorder for deeds; your attorney or the entity's registered agent for the agreements.

Schedules K-1 and owner basis records

Each K-1 you received from a partnership, LLC or S corporation, with the basis and capital account detail.

Which pages and forms
Schedule K-1 (Forms 1065, 1120-S, 1041), Form 7203 (S corporation basis), Item L capital account, Section 704(c) and 743(b) detail, Section 754 election, debt allocation.
How far back
Last 3 years of K-1s. For basis, back to the year you first became an owner (basis builds year by year, IRC 705 and 1367).
Why it matters
The gain on an entity interest is figured from your basis in it, not from the entity's books.
Do not have it? Get it here
The entity's CPA or bookkeeper; request the K-1 package and the basis worksheet.

Cost basis for every lot, with purchase dates

Year-end brokerage statements and lot-level cost basis for each holding you may sell.

Which pages and forms
Form 1099-B or consolidated 1099 for the last 3 years, plus the lot detail: purchase date, cost, wash sale adjustments, stock splits, reinvested dividends.
How far back
Back to the purchase date of each lot. The holding period, long-term or short-term, and basis come from that date.
Why it matters
Long-term and short-term gains are taxed at very different rates. Without lot dates, the broker's default can overstate the gain.
Do not have it? Get it here
Your brokerage's online tax center (cost basis export), or call the transfer agent. Mutual fund and DRIP history is on the fund company's site.

Crypto exchange and wallet history

Complete transaction history from every exchange, wallet and platform, as CSV files.

Which pages and forms
Exchange CSV exports, wallet addresses used, Form 1099-DA where issued, transfers between your own wallets, staking, mining, airdrops and DeFi activity, and any crypto-tax software report.
How far back
From your very first purchase. Basis and holding periods run lot by lot (IRS Notice 2014-21: crypto is property; Rev. Proc. 2024-28: basis tracked wallet by wallet from 2025).
Why it matters
Without a complete history the cost basis cannot be proved, and an unproved basis can be treated as zero.
Do not have it? Get it here
Each exchange's tax center or account history export; a crypto-tax tool's "all-years" report; the blockchain explorer for wallet history.

Collectibles: how you got it, and what it is worth

Receipts, invoices, auction or dealer records and any appraisal for art, coins, metals, jewelry or other collectibles.

Which pages and forms
Bill of sale, provenance, certificate of authenticity, insurance appraisal, auction house consignment contract, how it was acquired (bought, gifted, inherited).
How far back
The acquisition paperwork, however old. Appraisals within the last 12 months.
Why it matters
Collectibles gains are taxed at up to 28% (IRC 1(h)(4)), and basis is hard to rebuild after the fact.
Do not have it? Get it here
The dealer or auction house that sold it to you; your insurer's schedule of valued items; a qualified appraiser.

Purchase price and improvements record for the home

Closing statement from the purchase and a list of major improvements with dates and costs.

Which pages and forms
Closing Disclosure or HUD-1, receipts for additions, roof, kitchens, landscaping, permits, and the cost of any sale from a prior home rolled into it.
How far back
From the date you bought it.
Why it matters
Gain on a home is price minus basis. The exclusion (IRC 121) covers up to $250,000 or $500,000 of it if you qualify; the rest is taxed.
Do not have it? Get it here
Escrow company, contractors, permit records at the city, your bank statements for large payments.

Proof you lived in it: 2 of the last 5 years

Anything showing the home was your main home and when.

Which pages and forms
Driver's license and voter registration addresses, utility bills, tax returns showing the address, and dates of any rental, business use or absence.
How far back
The last 5 years before the sale date. The test is 2 years of ownership and use in the 5 years ending on the sale (IRC 121(a)). Also the date of any other home you sold with the exclusion, because it can be used once every 2 years (IRC 121(b)(3)).
Why it matters
Whether the exclusion applies, partly or fully, is the single biggest swing on a home sale.
Do not have it? Get it here
Your own utility and bank records; your CPA's file; the county for homeowner exemption records.
2

Send next

Sharpens the numbers.

Earlier 1031 exchanges: every one, back to the original purchase

The Form 8824 and closing statements for each exchange in the chain that led to this property.

Which pages and forms
Form 8824 for each exchange, both closing statements (relinquished and replacement), the qualified intermediary's exchange accounting, and the original purchase closing statement of the first property.
How far back
Back to the first property in the chain, however many years. Basis and depreciation carry over from exchange to exchange (IRC 1031(d)), so the chain is the basis.
Why it matters
A property bought in 2024 may carry a 1996 basis. Missing one link makes the basis, and the tax, a guess.
Do not have it? Get it here
Your CPA's files, your title or escrow company for each deal, the qualified intermediary (they keep exchange files), and the county recorder for old deeds.

Capital improvements, with dates and costs

A ledger of everything you added or replaced that was capitalized rather than expensed.

Which pages and forms
Date, vendor, cost, description, and the depreciation treatment. Include tenant improvements, roofs, paving, wells, fencing, drainage and building additions.
How far back
From the date you acquired the property.
Why it matters
Each dollar of improvement is a dollar less of gain. Many owners leave thousands of dollars on the table here.
Do not have it? Get it here
Your CPA's depreciation schedule, the property manager's capital expense log, bank statements, permits.

Any installment sale or seller note you already have

Paperwork for any sale where you are being paid over time, and any note you hold.

Which pages and forms
Form 6252 for each year, the note, the deed of trust or security agreement, the amortization schedule, and the latest payoff.
How far back
Every year until the note is paid in full (Form 6252 is filed each year payments arrive).
Why it matters
Large notes trigger the Section 453A interest charge once outstanding installment obligations pass $5,000,000 (IRC 453A(b)), and a note pledged as security is treated as a payment (IRC 453A(d)).
Do not have it? Get it here
Your CPA's files and the note servicer. Your attorney holds the signed note.

Losses and credits carried forward

The worksheets that track what you can use against the gain.

Which pages and forms
Passive losses by activity (Form 8582 and the worksheets behind it), capital loss carryover worksheet (Schedule D), net operating loss schedule, charitable contribution carryover, at-risk (Form 6198), foreign tax and general business credits, alternative minimum tax credit (Form 8801), Section 163(j) disallowed interest.
How far back
Back to the first year each loss arose. Suspended passive losses carry forward with no time limit and are released on a taxable disposition (IRC 469(g)). Capital losses carry forward without limit (IRC 1212(b)). Charitable carryovers last 5 years (IRC 170(d)(1)). Credits 20 years (IRC 39).
Why it matters
A $400,000 suspended loss can wipe out a large part of the gain, but only if it is tracked. An installment sale can delay when it is released.
Do not have it? Get it here
your CPA or tax software: ask for "every carryforward schedule as of last year". Also look in the Form 1040 instructions' worksheets.

Form 4797 and Schedule D history

Earlier years' reports of business-property sales and capital gains.

Which pages and forms
Form 4797 Parts I to III, Form 8949 and Schedule D, and any Section 1231 loss in the earlier years.
How far back
Last 5 years: net Section 1231 gain is taxed as ordinary income to the extent of net Section 1231 losses from the prior 5 years (IRC 1231(c)).
Why it matters
A loss taken three years ago can turn this year's capital gain into ordinary income.
Do not have it? Get it here
your CPA or tax software, the Form 4797 pages of each return.

Your income picture for the next 10 years

A short list of what else you expect to earn, receive or sell, year by year.

Which pages and forms
Wages or business income, Social Security start date, pensions, required distributions from retirement accounts, other planned sales, Medicare enrollment date, filing status and expected changes (marriage, death, move).
How far back
Today forward, 10 years. Medicare premium surcharges (IRMAA) are set from your tax return from 2 years earlier, so a 2026 sale shows up in 2028 premiums.
Why it matters
Spreading a gain only helps if the other years have room. This item tells us how much room each year has.
Do not have it? Get it here
Your last 2 returns, the Social Security Administration statement (ssa.gov/myaccount), your retirement account's RMD projection, your CPA's tax projection.

Estimated tax payments and year-to-date income

What you have paid and earned so far this year.

Which pages and forms
Form 1040-ES payments and dates, state estimates, year-to-date pay stubs or profit and loss, and any CPA tax projection for this year.
How far back
This year to date, plus last year's total tax (for the safe-harbor rules, IRC 6654).
Why it matters
A large sale mid-year can trigger underpayment penalties unless the payments are planned.
Do not have it? Get it here
IRS Online Account shows payments; your bank statements; your CPA.

State of residence for each owner, and any planned move

Where each owner lives and files, and whether a move is planned before or after closing.

Which pages and forms
Address history, driver's license state, days spent in each state (a simple calendar log), a new home purchase or lease, and the planned move date.
How far back
Current, plus the last 2 years of days-in-state. States audit residency claims with calendar and card records.
Why it matters
Moving from a high-tax state before the gain is recognized can change the bill by tens of thousands of dollars, but only if the dates work.
Do not have it? Get it here
Your own calendar, credit card and phone records, the new state's registration receipts.

Your goals and limits

A few lines on what the money is for and what you will not do.

Which pages and forms
Cash needed at closing and why, debts to retire, income you want and when, whether you want to stay in real estate or in the business, heirs, charitable intentions, your comfort with an IRS question, and how much paperwork you will tolerate.
How far back
Today and the next 10 years.
Why it matters
The best path depends on the goal more than on the tax. Two owners with the same gain can need different answers.
Do not have it? Get it here
Just write it in the notes box below. Rough is fine.

Your advisors, and permission to talk to them

Names and contact details for your CPA, attorney, broker, lender and qualified intermediary, and a note that Hans may speak with them.

Which pages and forms
Name, firm, email, phone. Tick the permission box in the form, or tell us who not to contact.
How far back
Current.
Why it matters
Hans works with your CPA and attorney, not around them. One call can save weeks.
Do not have it? Get it here
Your engagement letters or email signatures.

Rent roll, leases and profit and loss statements

Current rent roll, leases (or the lease abstracts) and 3 years of income and expense.

Which pages and forms
Rent roll with lease dates and rents, security deposits, tenant improvement or free-rent obligations, trailing 12-month and 3 years of profit and loss statements, property tax bills and insurance.
How far back
Last 3 years of operating statements, current rent roll and leases.
Why it matters
Income is what supports a buyer's price, a seller note, or a replacement loan, and the lease terms limit what a buyer can pay.
Do not have it? Get it here
Your property manager, your accounting system, Schedule E for the totals.

Appraisal, broker opinion of value or comparable sales

Any independent estimate of value.

Which pages and forms
Appraisal report, broker opinion of value, comparable sales, tax assessor's value split between land and improvements.
How far back
Most recent, within 12 months if possible. Add the one used when you bought, financed or inherited.
Why it matters
The land and building split changes depreciation recapture. A low appraisal in a seller-carry deal can limit the loan.
Do not have it? Get it here
Your lender (they hold the appraisal), a local broker, the county assessor's public record.

If you inherited it or were given it

The paperwork that sets your basis.

Which pages and forms
Inherited: date-of-death value (appraisal or estate return Form 706 and the beneficiary statement Form 8971), the will or trust, and the probate order. Gifted: the donor's basis and gift date (Form 709), and the donor's depreciation if it was rental property.
How far back
Back to the date of death or the date of the gift. Inherited assets get a stepped-up basis to date-of-death value (IRC 1014); gifts carry the donor's basis (IRC 1015).
Why it matters
A date-of-death basis can erase decades of gain. If it is not documented, the IRS can treat the basis as the donor's or as zero.
Do not have it? Get it here
The executor or probate attorney, the estate's CPA, or a retrospective appraisal by a licensed appraiser. County recorder for the deed and probate filings.

Cost segregation study or bonus depreciation records

Any study that moved parts of the building into short-lived categories, and the bonus depreciation taken.

Which pages and forms
The study report, the asset classes, Form 4562 lines, and any later changes.
How far back
From the year of the study.
Why it matters
Short-life property (IRC 1245) is taxed back as ordinary income, up to 37% (2026), when sold.
Do not have it? Get it here
The firm that prepared it, or your CPA's depreciation workpapers.

Time logs, if you claim real estate professional or material participation

Calendar or log of hours you worked in the property or business.

Which pages and forms
Hours by activity, and your other work hours if you work elsewhere (750 hours and more than half your working time to qualify, IRC 469(c)(7); 500 hours is one test for the business).
How far back
Each year you claimed the status. Courts require contemporaneous records, not after-the-fact estimates.
Why it matters
Whether losses were passive, and whether the 3.8% net investment income tax applies (IRC 1411), depends on it.
Do not have it? Get it here
Your calendar, emails, mileage logs, property manager reports.

Business financials: 3 to 5 years

Income statements, balance sheets and the entity tax returns.

Which pages and forms
Profit and loss and balance sheet by year, tax returns of the entity (Form 1120, 1120-S, 1065 or Schedule C), general ledger totals, accounts receivable and payable aging, asset list, goodwill and inventory detail, debt schedule.
How far back
Last 3 years minimum, 5 is better. Buyers price off 3 to 5 years, and the entity's tax basis and E&P come from the full history.
Why it matters
Goodwill, equipment, inventory and receivables are taxed differently, so the mix sets the tax.
Do not have it? Get it here
Your bookkeeping system, the entity's CPA, your banker's annual package.

Stock or ownership basis and entity type history

Where your basis in the business comes from.

Which pages and forms
Capital contributions, loans from owners, stock purchase agreement, S corporation election (Form 2553), any C corporation conversion, and Form 7203 for S corporations.
How far back
From formation or the date you acquired your interest.
Why it matters
Built-in gains tax (IRC 1374), C corporation double tax and whether you can use Section 1202 all turn on this history.
Do not have it? Get it here
The corporate minute book, your attorney, the entity's CPA.

Qualified small business stock (Section 1202) records, if any

Proof that your shares qualify for the exclusion.

Which pages and forms
Stock certificate or cap table, issue date, evidence the issuer was a C corporation with gross assets under the limit when the stock was issued ($50,000,000; $75,000,000 for stock issued after July 4, 2025), original-issue purchase records.
How far back
From the date the shares were issued to you. For stock issued after July 4, 2025 the exclusion is 50%, 75% or 100% at 3, 4 or 5 years; earlier stock needs 5 years (IRC 1202).
Why it matters
A qualifying holder can exclude a large part of the gain, so it must be documented before the sale.
Do not have it? Get it here
The company's attorney or finance team; your original subscription agreement.

Employment, consulting and non-compete terms

What you will do for the buyer and what you agree not to do.

Which pages and forms
Draft employment or consulting agreement, non-compete and non-solicit terms, and how much of the price is allocated to them.
How far back
The current deal.
Why it matters
Money paid for a non-compete or consulting is ordinary income, not capital gain.
Do not have it? Get it here
The buyer's draft documents, your deal attorney.

Farm income history: Schedule F

Schedule F with the supporting detail, and any income averaging.

Which pages and forms
Schedule F for 3 to 5 years, Schedule J (income averaging uses the 3 prior years' taxable income), Form 4797 for sales of breeding animals and machinery, CRP or other USDA payments, crop insurance, patronage dividends.
How far back
Last 3 years minimum, 5 better. Schedule J looks back at the 3 prior base years.
Why it matters
Farm sales can be mixed (land, equipment, livestock, inventory) and each part is taxed differently.
Do not have it? Get it here
Your farm CPA, the local Farm Service Agency office (for program payments and acreage reports).

Land records: deeds, surveys, leases, easements and programs

What encumbers or enhances the land.

Which pages and forms
Legal description and survey, farm or grazing leases, water and mineral rights, conservation easements, enrolled programs (CRP, EQIP) and their contracts, Section 2032A special-use valuation records if the land was inherited, soil and water conservation deductions taken (Section 175).
How far back
From acquisition. Section 1252 recaptures conservation deductions as ordinary income if you sell within 10 years of acquiring the land; Section 2032A recapture runs 10 years from the death.
Why it matters
Land use programs and easements can limit what a buyer will pay and add recapture.
Do not have it? Get it here
County recorder and assessor, the Farm Service Agency, NRCS, your attorney, your lender.

The buyer: who it is, any relationship to you, and how they will pay

Name, entity, how they are related to you (if at all), and their financing.

Which pages and forms
Buyer name and entity, relationship, proof of funds or lender commitment letter, and, if you will carry a note, the buyer's financial statement and the collateral you would get.
How far back
The current deal. Related-party sales have a 2-year rule on resale (IRC 453(e)).
Why it matters
A related buyer, or a buyer who may resell soon, can accelerate the tax. A seller note is only as good as the buyer and the collateral.
Do not have it? Get it here
The buyer's broker or attorney; a credit report and title search if you are carrying the note.

Home office, rental or other business use

Any part of the home used for rent or business, with the depreciation taken.

Which pages and forms
Form 8829 and depreciation schedules, rental periods and dates, Schedule E for rental years.
How far back
Back to May 7, 1997 for depreciation taken on the home (not covered by the exclusion, IRC 121(d)(6)), and to January 1, 2009 for periods it was not your main home (IRC 121(b)(5)).
Why it matters
Depreciation and non-home periods are taxed even when the exclusion applies.
Do not have it? Get it here
Your CPA's workpapers and your tax returns for those years.

Employer stock, options and restricted stock records

Grants, exercises and the tax forms for each.

Which pages and forms
Forms 3921 and 3922 (option exercises and ESPP), Form 83(b) elections, grant agreements, Form 6251 alternative minimum tax history and the Form 8801 credit, and net unrealized appreciation in employer stock inside a retirement plan.
How far back
Back to each grant. Holding periods start at exercise or vesting, not grant, and the AMT credit can carry forward many years.
Why it matters
These decide basis and whether gain is capital or ordinary.
Do not have it? Get it here
Your employer's equity plan portal (Fidelity, Schwab, E*Trade and others), the plan administrator, your CPA.

Margin loans, pledged shares and wash sales

Debt secured by your holdings and any losses you sold within 30 days of buying the same thing.

Which pages and forms
Margin or securities-based loan statement, pledge agreement, wash sale detail on the 1099-B.
How far back
Current loans; wash sales for the last 61-day window around each loss sale (IRC 1091).
Why it matters
Pledged shares limit what can be sold, and wash-sale-disallowed losses change your usable losses.
Do not have it? Get it here
Your brokerage's loan desk and tax center.

Any gain you have already deferred

Records for a gain you put into a Qualified Opportunity Fund or another deferral.

Which pages and forms
Form 8997 and Form 8949 for each year, the fund's annual statements, and the date of investment. Gain deferred under Section 1400Z-2 is included in income on December 31, 2026 (IRC 1400Z-2(b)(1)).
How far back
Back to the date of each investment.
Why it matters
That deferred gain comes due this year, on top of whatever you sell now.
Do not have it? Get it here
The fund manager's annual statement; your CPA.

Estate planning documents

Trusts, wills and powers of attorney that affect the asset.

Which pages and forms
Revocable and irrevocable trust agreements, will, beneficiary designations, any gifting or generation-skipping plans, buy-sell agreements. The federal estate tax exemption is $15,000,000 per person for 2026 (IRC 2010(c), as amended in 2025).
How far back
Current, plus any change in the last 5 years.
Why it matters
Basis step-up at death can make holding better than selling, and a trust owner changes who pays the tax.
Do not have it? Get it here
Your estate attorney.
3

Nice to have

The more the better.

Returns from 4 to 7 years ago

The same complete returns, going back further.

Which pages and forms
Same forms as the first item.
How far back
Years 4 through 7. They reveal carryforward origins, older exchanges and installment sales, and loss years.
Why it matters
It lets us trace a loss or a basis to its source if the later returns only show a total.
Do not have it? Get it here
Your CPA; IRS Form 4506 can get copies of older returns (generally about the last 7 years).

Your CPA's workpapers and a tax projection

Anything your CPA has prepared for this sale.

Which pages and forms
Tax projection or memo for the sale, depreciation workpapers, basis calculations, planning emails.
How far back
Current.
Why it matters
It shows what your CPA already assumes so the analysis lines up with their advice.
Do not have it? Get it here
Ask your CPA for "the file for the sale."

Property reports: title, survey, environmental, zoning, taxes

Reports that affect value and marketability.

Which pages and forms
Preliminary title report, ALTA survey, Phase I environmental, zoning letter, property tax bills and appeals, insurance loss runs.
How far back
Current, last 3 years of tax bills.
Why it matters
Issues here can change the price or the closing date, and the tax follows the price.
Do not have it? Get it here
Title company, county assessor, your insurance broker.

Tenant estoppels, deposits and capital plan

What the tenants will confirm and what is due.

Which pages and forms
Estoppel certificates, security deposit ledger, capital expenditure plan, deferred maintenance list, management agreement.
How far back
Current.
Why it matters
Open items can lead to a price credit or a delayed closing.
Do not have it? Get it here
Property manager and tenants (through the buyer's request).

Replacement property or exchange plans

If you want to exchange, what you are looking at.

Which pages and forms
Qualified intermediary agreement (if signed), identified properties, replacement purchase contracts, financing commitments. Identification closes 45 days and the purchase 180 days after you sell (IRC 1031(a)(3)).
How far back
Current deal.
Why it matters
Exchange rules start the clock at closing, so the plan has to exist before it.
Do not have it? Get it here
Your qualified intermediary, your broker.

Anything else you think matters

Photos, letters, notes about history, partners, disputes, easements, pending lawsuits or IRS notices.

Which pages and forms
Open IRS or state notices, disputes, pending claims, side agreements.
How far back
Any.
Why it matters
Surprises late in the process cost the most. A short note now helps.
Do not have it? Get it here
Your files and memory. Rough is fine.

Rules cited are federal Internal Revenue Code sections as of October 10, 2026. Time limits and thresholds change; your CPA confirms the current rule for your year. Not tax, legal or financial advice. Hans is not a CPA, attorney or registered investment adviser; the analysis models tax effects and does not recommend specific securities.

Download the list for another asset type
Send it

Tell Hans what you have

Fill in what you know. Only your name and email are required. Upload now, or tick the boxes in the list above for what you have and send the files later.

The boxes you tick in the list above count as "documents I have". None ticked yet.

Upload documents (optional)

How your files are handled. They travel over an encrypted connection and are stored in private storage with no public web address. They are never emailed, never attached to a CRM record and never shown on a web page. Only Hans retrieves them, to a restricted folder on his own computer. Storage deletes them automatically within 45 days. Please black out Social Security numbers and bank account numbers first (leave the last four digits). Privacy policy.

    By submitting, you agree that Hans Goldstein: Tax & Exit Planning may email you about this request, including one confirmation email with your list of what is still to send. Unsubscribe anytime. If you add a phone number, you agree that Hans Goldstein may call you at that number about your request. Optional; consent is not a condition of purchase.

    Questions

    About the checklist

    What documents do I need to calculate capital gains tax on a property sale?

    Four things decide the number: the price (the sale contract and the closing statement), your basis (the closing statement from when you bought it plus the cost of improvements), depreciation taken (the depreciation schedule and Form 4562 from your returns) and what else is on your return (your last 3 years of federal and state returns with every schedule). Loan payoff statements and how you hold title complete the picture. This page ranks everything else by how much it changes the answer.

    How far back do I need to go?

    Three years of tax returns is the minimum, because the IRS normally has 3 years to assess tax (IRC 6501(a)). Five to seven is better because losses and credits carry forward: passive losses with no time limit, capital losses with no time limit, charitable carryovers 5 years, net Section 1231 losses are looked at 5 years back, and a property acquired through earlier 1031 exchanges carries its basis from the first property in the chain, however many years ago. Each item above says how far back and why.

    What if I do not have the closing statement from when I bought it?

    Ask the title or escrow company that handled the purchase; they usually keep files for years. The county recorder has the deed and the transfer tax paid, which often shows the price. Your CPA's depreciation schedule shows the basis they used. Your lender's closing package is another copy. If none of these exist, tell us what you remember; the analysis will flag the basis as an estimate.

    Do I need all of this before you can start?

    No. The first tier is enough to start, and you can send it in pieces. If you only have time for one thing, send your last two complete tax returns and the sale contract or listing.

    Is it safe to upload my tax returns?

    Files are sent over an encrypted connection and stored in private storage that has no public address. No file is ever emailed, attached to a CRM record, or shown on a web page. Only Hans retrieves them, to a restricted folder on his own computer. Please black out Social Security numbers and bank account numbers before you upload (leave the last four digits). If you would rather not upload, tick the boxes for what you have and send nothing; the form works without files.

    How long do you keep what I upload?

    Files in the upload storage are deleted automatically within 45 days. Hans keeps the copy on his computer only as long as your analysis is open and deletes it when you ask. Read the privacy policy.

    Where can I get free IRS transcripts of my returns?

    Create or sign in to your IRS Online Account at irs.gov/account. Return transcripts are available for the current and three prior years, and a transcript is a summary rather than the full return. For the complete return with every schedule, ask your CPA or tax software. For older copies, the IRS Form 4506 request covers roughly the last seven years.

    I am a CPA, attorney or broker sending this for a client. Can I use the form?

    Yes. Pick your role in the form. Please send only what your client has agreed to share, and tick the permission box in the notes about who Hans may speak with.

    Education and analysis, not tax or legal advice. Hans is not a CPA, attorney or registered investment adviser; the analysis models tax effects and does not recommend specific securities. The analysis is an educational comparison to bring to your own CPA and attorney.

    Book a callCall Hans