Tax Efficient Way to Cash Out of Stocks to Purchase Property

[Syed Rizvi]

Hi BPer's,

I'd like to convert some of my stock and bond holdings to cash and then purchase an owner-occupied investment property with those funds (using the FHA loan, probably less than 10% down payment). I have held most of my stock and bond holdings for 2-3 years, so that should trigger the long-term capital gains tax (I have 6-7% unrealized gains). However, I am wondering if there is a better way for me to most tax efficiently convert these liquid assets into a real estate investment--much like how the 1031 Exchange works for real estate to real estate conversions.

Also, I may consider dipping into my Fidelity IRA and my 401K to purchase the property (as in, take out a loan from my IRA and/or my 401K). Is that wise?

Please feel free to message me privately as well. Really appreciate all of your advice! Thank you so much!