Custom Checkout Real Estate Photography

I am developing a Site for real estate photography services.

I want to be able to provide my customers with a custom check out.

For example, depending on the square foot of their home, I want to be able to show them certain prices for which ever services they are interested in.

So if their home was 1500 square-foot they could choose to put a service into their cart for $150.

But if their home is 2500 square-foot they would be shown a price point of $250, Not the lower price points.

Is this possible?