I own a lot of shares in a company that has done very well on the market recently. So well in fact that if I sold it all now, I could divide the proceeds equally between my two kids and set them both up for college — something my parents couldn't do for me. However, my oldest child won't be ready for college for another 12 years. Is there any way to convert the stock shares into something less volatile than the market, without incurring capital gains tax? My kids both have 529 funds and I'd love to be able to move the stock there but I want to avoid the IRS as much as possible. Yes, I am naive and ignorant of the finer workings of finance, so please be gentle.
posted by Ratio on Oct 30, 2011 - 13 answers

Recovered escheated stock in Massachusetts - how is it taxed? [more inside]
posted by plinth on Apr 12, 2010 - 1 answer

When I was younger, my parents bought me several shares in Disney. I'd like to sell that stock now. What do I have to do to do so, and what taxes, etc. might I incur on it? [more inside]
posted by Mali on Jan 20, 2010 - 14 answers

My partner and I need to pay off some debt, and unfortunately we need to dip into our retirement funds. Our tax accountant is on vacation and we can't find the answer to our question. We have two sources–either sell some stock or cash out a couple of short-term IRA CDs. Which is the lesser of two evils? [more inside]
posted by al_fresco on Dec 13, 2008 - 11 answers

[Tax/Stock Filter:] Employee Stock Purchase Plan advice especially in re: taxation [more inside]
posted by jckll on Dec 11, 2008 - 5 answers

I have exercised stock options and taken possession of a small number of shares. I have not sold anything, but am wondering how screwed I am, tax-wise. First, do I have to declare the value of the stock as "income" for the year that I acquired it? Second, if I should sell it, do I add the money I receive from that sale to my regular taxable income? Do I deduct the amount I paid in? Is the net difference subject to other taxes? Is this handle-able by an average person or do I need an accountant?
posted by scarabic on Jan 13, 2005 - 6 answers