Our home currently (1st photo)

& "Nantucket dormer" examples

I would leave the dormers, they look fine. The house looks a bit plain. I would spend my money on a nice large sitting type porch, with a roof across the front. That will give your house a lot of curb appeal, and the dormer wont. Something more like this.

Jennifer, Charles Ross Homes above answered the question in the OP.

This isn't the same as buying a product from Amazon and having it shipped to you.

You can't get pricing for major construction over the net and have it be accurate for your area. A reputable contractor needs to come to your home and give you an estimate based on the work you plan to do. For accuracy you will need the specifications to provide to the contractor so you can get an accurate estimate. Labor is local and will affect pricing. Your specs may be different than the OP's specs so the "super rough ballpark" that you suggested doesn't work either unless you have a quote like: Anywhere from $10k to eleventy million - a quote so wide it's meaningless but protects the contractor from surprises. Spend the money to determine the specs and put them out to bid. Good luck!

No way that you can rebuild a roof and then and reroof it all for 10K. Triple that as the lowest lowball start. 10x that for possible required bringing everything up to code and current required headroom and stair access.

Are you hoping to remove the side walls of the dormers when it is opened up, or can the center section just be popped up leaving the existing dormers? Makes a big difference in degree of difficulty and cost.

@Amy Christine, curious to know if you ever tackled this project? We are purchasing a cape cod style home and I would like to connect the two doghouse dormers to create a shed or nantucket dormer.

Thank for input from all! we did end up changing our minds it seems to be unnecessary in the end I do like the look for a new build. we did redo siding and windows are next its a very old house there are so many issues to tackle! there are many layout issues that need correction and kitchen closet and bath upgrades but trying to get good ROI for what we put into it so we can move off this busy road to a nicer area of the island and either build new or find something we would love to make our own! this house is jsut one thing after another unfortunately..hoping the future holds the perfect home for us!

@Lianne ended up being as they say biting off more than we can chew..however I would like to if possible if it becomes a forever home (something I hope to avoid) lol then I MUST attach a new garage to the home and make the above a master with a master bath. right now we have the 3 tiny sloped rooms and 1 TINY shared bath it is absolutely ridiculous even for a starter home in my opinion so after playing with the Floorplan I have about 3 versions I could live with. I very much hope that addition will at least be possible in the future for us as well as you yours! it's such a beautiful look.

@Amy Christine I completely get the biting off more than you can chew bit! From looking online it looked like the conversion wasn't really worth the money it would cost. I was really hoping to open up the rooms a little to create more usable space. But there are quite a few projects to undertake. I'll just file that dormer expansion thought under the "we had this idea once". Thanks for responding. I wish you the best with your floor plan!