I would say best legit outlet is Paradigm PC's $140.37.  Free shipping. 
Last time I got one via them it was a boxed scratch card one.

They might be drop-shipped direct from from wholesaler so could be a wait over holiday period.   Could contact them and find out.

Noel Leeming might price match - "New Zealand retailer website product offers will be considered where the product meets all    relevant criteria"

"Legit" status unknown - Tradme
I got my last one (July) from seller 'yurix'.  I wont link direct but its easy to find currently at $98.90
Paid via ping (credit card) and get trademe 30days buyer protection.
They seem to be either operating on low margin/high turnover or issuing OEM type subscription keys. The key gets emailed to you in a couple of days per description.

I'm not endorsing them just advising I haven't had any issues and they seem to have done a large number of sales with minimal negative feedback.

Yeah the TM guy feels a bit sketchy. He has the same thing listed at two different prices and is selling Windows Server 2022 for $90, no chance that's legitimately sourced, though subscriptions are harder to 'cheat'.

Having said that, I paid $109 last year for my family pack, and $99 seems a great deal and I likely get it very soon....

Still works, thanks @wakrak

Give this a try if your employer uses Microsoft 365 https://www.microsoft.com/en-nz/workplace-discount-program

DjShadow:

 

Give this a try if your employer uses Microsoft 365 https://www.microsoft.com/en-nz/workplace-discount-program

 

 

 

Caveat: Officially, this license is only valid whilst you are working for that employer. From memory, you have to sign up with your work email address.

DjShadow:

 

Give this a try if your employer uses Microsoft 365 https://www.microsoft.com/en-nz/workplace-discount-program

 

FYI it seems to be $125.70 via this route (or at least it is for me).

DjShadow:

 

Give this a try if your employer uses Microsoft 365 https://www.microsoft.com/en-nz/workplace-discount-program

 

Many thanks for this. Mine was set to expire at the beginning of next month, so happy to save more than $50 :)

ANglEAUT:

 

DjShadow:

 

Give this a try if your employer uses Microsoft 365 https://www.microsoft.com/en-nz/workplace-discount-program

 

 

 

 

Caveat: Officially, this license is only valid whilst you are working for that employer. From memory, you have to sign up with your work email address.

 

 

 

You do need to sign up with the work email address but even if you no longer work for the company, it should renew at the discounted rate as long as the subscription is continued. as per link above:

Enjoy the full benefits of Microsoft 365 apps with more features and extras, one TB of cloud storage and advanced protection for your data and devices. Microsoft 365 Family and Personal annual subscriptions are 30% off for Workplace Discount Programme eligible customers.1 Plus, the discount continues for as long as you maintain recurring billing.

Speaking of purchasing Windows software - does this place look legit? https://hypestkey.com/product/windows-10-home/