And the main concern for the soon-to-be-mums is not usually the impending birth, but survival.
"Usually having the baby is probably about the last thing on their minds. There's more stress in the fact they've got nowhere to live and are usually cold and hungry and broke and often have addiction problems.
"I probably am the only one who looks after homeless pregnant people [in Auckland]. For me, I'm looking after three streeties at the moment who are pregnant and there's probably a couple more out there seeking midwifery care."
The lack of emergency housing set up for pregnant homeless women in Auckland was part of the issue, Ms Winder said.
She said new mothers also had difficulty finding housing or emergency accommodation once they gave birth.
"There is nowhere specifically for pregnant women, we haven't got places for women with mental health issues either, or lots of people that need specialist care."
Emergency housing provider Danielle Bergin, of Island Child Charitable Trust which usually takes in homeless families, said living on the street or in temporary accommodation was particularly hard for pregnant women.
She was currently housing a mother with a 4-month-old baby who had been pregnant when she applied for a home.
About a year ago, Ms Bergin took in a 28-year-old woman who was heavily pregnant. The woman had the baby and then was forced to return to the emergency housing room in Pt England.
"Here we are a year later, has anything changed? I'm finding it so hard to get the houses now. For families or mothers with babies I'm finding it incredibly hard, there are such long delays.
"There are some serious delays in people having their applications completed and they think they're on the [social housing] waiting list but they're not.
"It's very worrying for women who are so close to birth, there is a nesting instinct. I do think it causes undue stress."
Lifewise service manager Corie Haddock said the sector was seeing an annual increase in homelessness and marginalised groups, including pregnant women, were the hardest hit.
The organisation was currently looking after one pregnant woman and has helped women who were more than 8 months' pregnant in the past, he said.
It was "hard to quantify" whether more homeless women were becoming pregnant or more pregnant women finding themselves without a home, he said.
"I think they all want to be good mothers so that pressure of not having somewhere safe and secure to live and for their baby to live must have a detrimental impact on them.
"[We help] anyone and everyone that comes through the door needing support. We've had situations in the past where we've had young women that are pregnant and I guarantee we'll have situations in the future as well."