Not avoid but possibly delay.  How about a 1031 exchange?

He should talk to his accountant.

Yup talk to your CPA about the 1031 exchange.

Avoid making a gain? 

There may be tax planning strategies that may be available to minimize tax on capital gains.  Your friend should discuss with his professional tax advisor(s).  He should not rely on comments provided in a Q&A forum.  There is insufficient information in your question to even provide any answer.

This is a question only the accountant can answer, not a good friend. I have had people do 1031 exchanges as Michael Jacobs mentions but the person needs professional advice of a CPA.

Val.

1031Exchange as my friend Michael Jacobs stated.  It is often used in commercial real estate.  Also he should consult his CPA and or financial advisor. A

Between Michael Jacobs and Gita Bantwal you have the answers.

1031 exchange

IRS bloodhounds will come a sniffing when the word AVOID is used...woe

Michael Jacobs delivered it.

Michael Jacobs has the best possible answer for your friend.

Talk to a CPA who is skilled with 1031 exchanges.

Val Evans A 1031 Exchange will defer the taxes. This is a 'like kind' exchange so it shouldn't be a problem.

First - have your client talk to his accountant about tax free exchanges. You really don't want to be getting tax advice from ActiveRain - no matter how smart we are! 

 Good Friday morning Val. I was thinking the same thing that Michael was.

I refer my clients to my vendor who specifically advise them on this issue. 

Pose that Q to a qualified 1031 intermediary, and CPA/tax accountant to see if the transaction qualifies, and if it makes sense to do BEFORE selling or buying. Old Republic down your way has done many of ours.

Mind you giving tax advise to clients instead of suggesting a tax attorney or CPA can land an agent in deep poo poo 

1031 exchange would be my first thought, but always consult a tax accountant or lawyer.  Don't know if you can go from multiple residential rentals to a single commercial property though.  Definitely need to check with a tax lawyer.

Your friend should probably consult with their accountant. That's what I would recommend.

Just a 1031 exchange, unless he wants to convert to his primary residence and sell in 2 years. 

Sorry, can't help you. I am not a lawyer nor a tax attorney.

A 1031 will delay the pain in the pocketbook.

I think one way is to make capital improvements to the home as that will offset part of the gains...and allow to sell at higher price to help pay for some of the capital gains.  I think the $250,000/$500,000 only applies to your primary residence.  I also think that expenses when selling a house are tax deductions, too.

I think another option might be to sell some stocks at a loss.

But, the best thing would be to talk to an accountant.

If it's personal residence then capital gains are avoidable and if it's investment then 1030 exchange or sell it for less than what you paid 

You need to ask an accountant that question. We are merely Realtors.