The IRS requires individuals to substantiate all charitable donations, regardless of the amount, with bank records (canceled check or bank statements) or a receipt from the charity. Yes, this includes the $1 you toss into the Goodwill buckets during the holidays and that extra $5 you toss into the second collection at Sunday Mass! Make sure that you receive a receipt from all of your donations from the charity in the year in which you made them. For donations in excess of $250, you must obtain a receipt from the charity on or before the date you file your tax return, including extensions.
As a reminder, the charitable organization must be a tax-exempt organization which is for religious, charitiable, educational, scientific or literary in purpose. Qualified organizations include churches, boy scouts and non-profit schools. Unqualified organizations include lodges, civic leagues, labor unions, political organizations, political canidates, and most foreign organizations.
In addition, all items donated to charity must be in good or better condition. How this can be proved is unknown, but it may be wise to substantiate your donation with a photograph of the item before you give it away and remember to keep good records and receipts.
Items with a single value in excess of $5000 need to be appraised, but may be in any condition. The qualified appraisal must be attached to your tax return.