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At 55, I have just retired. My non contributory company retirement plan is soley company stock of my privately held company. I have elected to receive the stock at cost basis as straight income of approx $90k. My date of retirement was March 24 of this year. The stock has appreciated approximately 300% above that cost basis.
The wife and I are planning to build our retirement home requiring approximately $200k of this stock to be sold. We have other assets but they are mostly the same company stock. My wife also worked for the same company and also has all her retirement in the same stock. Though she has stopped working, she has not formally retired and thus her retirement stock is still held by our company.
We are aware that having all our eggs in the same basket is not an accepted investment practice but we see no way out of this dilemma with out incurring a huge tax liability even though this will be at long term capital gains rate. Rolling this into an IRA does not seem to be advantageous because of my age. I would prefer not to deal with IRA 72(t) unless absolutely necessary
Add the required selling of stock for the house and you can see our tax problem will be outrageous.
we are not sure but believe we will owe approximately $26K of estimated taxes this next quarter just to pay off my distribution at cost basis.

I already posted this on the retired fools board and it was suggested that this board was more appropriate for my questions.

Any suggestions to minimize our tax liabilities short of not building the house would be appreciated.

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