Capital Gains Tax - Does this apply only to the actual “gains” or to the entire amount of my sale?
You normally only pay taxes on the difference between the sale price and the cost basis of the asset. In your example, you would probably pay taxes on the $10 difference, not the full sale price of $110. If you paid a commission, however, you would be taxed on your gain minus the commission you paid. Since you held the asset for less than a year, you wouldn't pay the long-term capital gains rate of 20%; you'd be taxed on the capital gain as if it were ordinary income, which depends on your federal income tax bracket. Also, littleadv makes a good point about the implications of buying the asset with after-tax funds too, so that's another part of the equation to consider as well. Assuming you bought the stocks with after-tax money, you only pay tax on the difference. Had you bought he shares in a pretax retirement account, such as an IRA or 401(k), the taxation waits until you withdraw, at which point, it's all taxed as ordinary income.
The dividend tax credit is not applicable to foreign dividend income, so you would be taxed fully on every dollar of that income. When you sell a stock, there will be a capital gain or capital loss depending on if it gained or lost value, after accounting for the Adjusted Cost Base. You only pay income tax on half of the amount earned through capital gains, and if you have losses, you can use them to offset other investments that had capital gains (or carry forward to offset gains in the future).  The dividends from US stocks are subject to a 15% withholding tax that gets paid to the IRS automatically when the dividends are issued. If the stocks are held in an RRSP, they are exempt from the withholding tax. If held in a non-registered account, you can be reimbursed for the tax by claiming the foreign tax credit that you linked to. If held in a TFSA or RESP, the withholding tax cannot be recovered. Also, if you are not directly holding the stocks, and instead buy a mutual fund or ETF that directly holds the stocks, then the RRSP exemption no longer applies, but the foreign tax credit is still claimable for a non-registered account. If the mutual fund or ETF does not directly hold stocks, and instead holds one or more ETFs, there is no way to recover the withholding tax in any type of account. "If you only have to pay 23k federal taxes on 100k, that means you are in the long term capital gains tax rate, which is the lower of the tax rates available. First you get your federal income tax marginal tax rate, and then find the matching long term capital gains tax rate. For example, if your marginal federal income tax rate is 28%, your capital gains tax rate would be 15%. Or rather, if the amount of the gain would put you in the 28% rate, then your long term capital gains tax rate is 15%. You can reduce that by having more losses. If you have anything else invested anywhere that is taking a loss, then you can sell that this year and it will offset the other gains you have realized. The only note is that your losses have to be long term capital losses too. Tax loss harvesting takes this to an extreme where you sell something at a loss to lock in the tax loss, but you didn't really want to get rid of that investment, so then you buy a nearly identical investment. ie. if you owned shares of ""Direxion Tech Sector ETF"" and it was at a loss, you would sell that and then immediately buy ""ProShares Tech Sector ETF"", the competing product that does the exact same thing. Then there is charity. This still requires spending money and you not having it any longer. If you feel that a cause can use the money more directly than the US government, you can donate an appreciated asset to the charity - not report a gain and also take a charitable deduction." First the good news: based on the time involved, and the amount of potential profits; you will not owe any tax on the sale of the house no matter which option you pick. Now the details. When determining if there are any capital gains the IRS cares about the difference between the sale price and the purchase price. The amount of the loan, the final balance of the loan, or the lack of loan don't factor into the calculation. To complicate matters the government does factor into the equation any improvements you have made to the house (like a new deck) and the cost of buying and selling the house (real estate agents). If a single person has less than 250K in capital gains and has used the house as their main residence for 2 of the the previous 5 years their tax is zero. For a couple the tax free gain is $500K. For your situation since the sale price is less than $250K, the capital gains will also be less than $250K. You do have one potential area of concern. If the house is worth significantly more than $150K, the government could claim that the difference between what you charged your parents and what you could have charged was a gift. Assuming that there are no other factors that you didn't include in the original question it would appear that you will not face any taxes. Regarding your two options, neither will impact the taxes. Though draining your savings or investments could make it difficult to meet an emergency during the time between the sending of the $95K to the mortgage company and the closing on the deal with your parents. If the money came from retirement account it could have an even greater impact on your taxes and retirement situation. There is a process called a backdoor IRA.   You now have effectively made a Roth IRA contribution in a year where technically you aren't eligible.  You do not have to pay taxes on earnings with a Roth IRA.  You are limited to the normal annual contribution to the IRA (Roth or traditional).   If you don't convert your traditional IRA contribution to a Roth IRA, then you are right.  That gains nothing except enhanced protection in bankruptcy.  Only do this if you are taking advantage of the Roth rollover.   I'm ignoring rolling over a 401k into an IRA, as that doesn't increase the amount you can contribute.  This does.  You can contribute the full $18,000 to the 401k and still make a full contribution to the backdoor IRA.   This is the tax advantaged form of an IRA.  This avoids double taxation.  Let's assume that your investment can go into something with a 5% annual return and you pay a 25% tax rate (doesn't matter as it drops out).  You are going to invest for thirty years and then withdraw.  You initially have $1000 before taxes.   With a regular investment:   You now have $2867.74.   With a pre-tax IRA.   You now have $3241.45 (it is not an accident that this is almost the same as the amount before the capital gains tax in the example without an IRA).   You avoided the $373.72 capital gains tax.  Even though you paid a lot more tax, you paid it out of the gains from investing the original $250 that you would have paid in tax.   This helps you even more if the capital gains tax goes up in the future.  Or if your tax bracket changes.  If you currently are in the 25% bracket but retire in the 15% bracket, these numbers will get even better in your favor.   If you currently are in the 15% bracket and worry that you might retire in the 25% bracket, consider a Roth instead.  It also avoids double taxation but its single taxation is at your current rate rather than your future rate. You likely received the shares as ordinary income for services of $10k, since they withheld taxes at granting.  Separately, you likely had a short term capital loss on sale of $2k, since your holding period seems to have been under one year. "You can exclude up to $250000 ($500000 for married filing jointly) of capital gains on property which was your primary residence for at least 2 years within the 5 years preceding the sale. This is called ""Section 121 exclusion"". See the IRS publication 523 for more details. Gains is the difference between your cost basis (money you paid for the property) and the proceeds (money you got when you sold it). Note that the amounts you deducted for depreciation (or were allowed to deduct during the period the condo was a rental, even if you chose not to) will be taxed at a special rate of 25% - this is called ""depreciation recapture"", and is discussed in the IRS publication 544." "-Alain Wertheimer I'm a hobbyist... Most (probably all) of those older items were sold both prior to my establishing the LLC This is a hobby of yours, this is not your business. You purchased all of these goods for your pleasure, not for their future profit. The later items that you bought after your LLC was establish served both purposes (perks of doing what you love).  How should I go about reporting this income for the items I don't have records for how much I purchased them for?  There's nothing you can do. As noted above, these items (if you were to testify in court against the IRS). ""Losses from the sale of personal-use property, such as your home or car, aren't tax deductible."" Source Do I need to indicate 100% of the income because I can't prove that I sold it at a loss? Yes, if you do not have previous records you must claim a 100% capital gain. Source Addition: As JoeTaxpayer has mentioned in the comments, the second source I posted is for stocks and bonds.  So at year begin of 2016, I started selling what I didn't need on eBay and on various forums [January - September]. Because you are not in the business of doing this, you do not need to explain the cost; but you do need to report the income as Gross Income on your 1040. Yes, if you bought a TV three years ago for a $100 and sold it for $50, the IRS would recognize you earning $50.  As these are all personal items, they can not be deducted; regardless of gain or loss. Source Later in the year 2016 (October), I started an LLC (October - December) If these are items that you did not record early in the process of your LLC, then it is reported as a 100% gain as you can not prove any business expenses or costs to acquire associated with it.  Source Refer to above answer.  Refer to above answer.  Conclusion Again, this is a income tax question that is split between business and personal use items. This is not a question of other's assessment of the value of the asset. It is solely based on the instruments of the IRS and their assessment of gains and losses from businesses. As OP does not have the necessary documents to prove otherwise, a cost basis of $0 must be assumed; thus you have a 100% gain on sale." You can keep the cash in your account as long as you want, but you have to pay a tax on what's called capital gains. To quote from Wikipedia: A capital gain is a profit that results from investments into a capital asset, such as stocks, bonds or real estate, which exceeds the purchase price. It is the difference between a higher selling price and a lower purchase price, resulting in a financial gain for the investor.[1] Conversely, a capital loss arises if the proceeds from the sale of a capital asset are less than the purchase price. Thus, buying/selling stock counts as investment income which would be a capital gain/loss. When you are filing taxes, you have to report net capital gain/loss. So you don't pay taxes on an individual stock sale or purchase - you pay tax on the sum of all your transactions.  Note: You do not pay any tax if you have a net capital loss. Taxes are only on capital gains.  The amount you are taxed depends on your tax bracket and your holding period. A short term capital gain is gain on an investment held for less than one year. These gains are taxed at your ordinary income tax rate. A long term capital gain is gain on an investment held for more than one year. These gains are taxed at a special rate: If your income tax rate is 10 or 15%, then long term gains are taxed at 0% i.e. no tax, otherwise the tax rate is 15%. So you're not taxed on specific stock sales - you're taxed on your total gain. There is no tax for a capital loss, and investors sometimes take profits from good investments and take losses from bad investments to lower their total capital gain so they won't be taxed as much. The tax rate is expected to change in 2013, but the current ratios could be extended. Until then, however, the rate is as is.  Of course, this all applies if you live in the United States. Other countries have different measures. Hope it helps!  Wikipedia has a great chart to refer to: http://en.wikipedia.org/wiki/Capital_gains_tax_in_the_United_States.