Money from Taxable account for home

[Sawbones]

I keep most of my money in Vanguard (VTSAX) and have been letting it accumulate over the past several years with monthly contributions. Now it is coming to pass that I need to withdraw a large amount for a downpayment (vs the entire payment) for a new home.
Are there any strategies to keep in mind when I "cash out" the index funds for cash? Which "cache" of investments does one take out first, the oldest, the newest, the ones that have the fewest gains (or losses) etc.
Thanks, all...

[Hank]

Long term capital gains with highest basis.

You could look into a pledged asset line, margin loan, physician loan, or loan from a bank affiliated with your brokerage to avoid the asset sale and long term capital gains. Estimate the total cost and risk, don’t let taxes blind you to the overall costs of your new mortgage.

[StarTrekDoc]

1. tax loss harvest on anything

then what Hank said.

[xraygoggles]

See if you can transfer your account from a regular brokerage account to a pledged asset line. Then use that to borrow from, without having to sell your underlying holdings. But it depends on how big the balance is, and how much you want to borrow for the down payment. Having concrete numbers would be more helpful.

[Tangler]

1. I would figure out how you want to pay.
If you are 30 with a lot of human capital and a long time until retirement then you want a small down payment.
If you are 80 then you want a large down payment.

2. sell the funds that are LTCG ( held for > 1 year, taxed as ltcg), with the lowest gains (lowest taxes)

3. use “specific id” when deciding which shares to sell.
This allows you to pick which shares to sell based on basis.