Pergolas are an inexpensive way to break up an expanse. I've seen them used when a split level ranch gets a second story designed to maximize additional square feet. That often creates an oddly high box, and a pergola along the front, at the line between the first and second stories, will make a world of difference. In this case, think about what expanse you are trying to break up. A pergola won't do much for shelter and it will create shade, so if light into the house is a concern think twice before doing this. My neighbor has one with wisteria that in the summer thoroughly blocks light, but it is used to disguise the side of the garage. (The big thing here is to turn the garage sideways, so it supposedly doesn't look like a garage from the street. But then you have this really odd wall that no one wants to put big windows in, so it gets various disguises. I have a feeling "what do I do with this" Houzz questions coming our way when this trend dies out). In your shoes I'd be thinking about how to visually lift the front facade - there's a lot of roof. I realize lots of people like roofs and that trendy houses have lots of roof expanse, but I've never been a fan. I have a flat roof hidden by a small parapet so my taste my not align with yours. To draw the eye up make that chimney more prominent and bigger: wrap it in a box and give it a brick veneer. If you are handy you can do that yourself. Be careful at the top that you follow all fire codes.

I built in SW FL. When I was designing the house, I wanted my studio to be smaller than it wound up, although I'm glad how large it is now. I was told that it would have cost more to put a beam across to hold the weight than to build the bigger room. As for your getting a cost per square foot, unless you have finished plans and have all your fixtures picked out, it's all bogus. Why is your kitchen 2x the size of your living space? Those sink vanities upstairs are barely large enough to hold a toothbrush, let alone any extras you need. I would HIGHLY recommend you post your kitchen layout in the Kitchen forum as it needs LOTS of help. I'm sorry but it's just poor design. What does the rest of the plan look like? What do the elevations look like? What direction is north?

As someone who lives in the Long Island/New York area, and has done a lot of construction and new building, I'll tell you that NOTHING is inexpensive here. Depending on where on LI you live, it will be more or less but ALL expensive. The South Fork of Suffolk County and the North Shore of Nassau are the most expensive, but anywhere on LI good labor is very sought after and therefore pricey. And if you're in an incorporated village, the permitting costs are also sky high. The cost of a total second floor would probably start in the low 6-figures and go up considerably from there depending on the details of your construction (see comments from the architects above). And don't discount the services of an architect. It's better to find out that you can't spend $250,000-500,000 on a renovation after spending a few thousand on an architect, than to start blindly and find out you can't afford it after blowing off the roof and you're in the middle of a snowstorm with only a tarp over your head. Any time I've added a room, either horizontally or vertically, I've used an architect. Money well spent.

We're nearby (MoCo) and recently did an addition to our small house. We think it was originally a small Cape or ranch and had two prior additions - one to expand the upstairs for a full second story (3br plus 1 hall bath) and a second addition to add onto the back. Those were done by previous owners in the 1980s, and the house needed a lot of updating along with more space. So we extended the second story over the back addition to make a primary suite for a total of 4br/3ba. We gutted much of the existing house and also added a porch off the back. Ours was not modular, so I'm not sure how much this helps but it was $$$ and basically was a year from when we signed the contract to when we will finish the punch list (this week.) For 6 months of the bulk of the work, we were in a rental house. We talked to a bunch of local design/build firms but ultimately went with an architect and a separate contractor. Just to give you a ballpark, our bids -exclusive of fixtures, appliances, lighting, plumbing and tile - ranged from $310k to $475k (the porch was separate, $60k.) The addition was 500sf but we also replaced all windows and doors, added a fireplace, removed a wall, etc. And yes, like you, it was still a lot cheaper than moving. I hear from our contractor and architect that they have more work than they can possibly handle for the foreseeable future. Hope this helps in your decisionmaking.