NaviJen, pleased to see you posting with us. Mass. is a whole different style of housing than what I'm used to in Alabama. Like lower ceilings, big basements, storm windows, dormers, angled ceilings upstairs. And I've been surprised at the absence of air conditioning (a necessity built into every home in south Alabama), and the intrusive nature of many heating systems--including radiators, baseboard heaters, boilers and oil tanks! Those things take up a lot of space and money to operate also. As older folks who married almost four years ago (second spouses), my DH has a home up there, and I have one down here. That's why I sometimes do a flip-flop from north to south, you will notice. I've been redoing his house AND mine. Jen, be sure to hang in there with us, a lot of creative ideas come from this group of folks. And Steph, you are so unique, giving your boy his own bedroom!!! I'm thinking you need to get out more? hehehehe Having huge antique furniture can be a drawback in a smaller home. Of course, ONE PIECE could fit, maybe, if it is a featured piece. Something that WORKS FOR ITS KEEP. I do hope you have room for the things you've STORED FOR 14 YEARS?!! At least, put it in place and see if it leaves enough breathing room. After all this time, you may have fantasized it into something it can never be, and you've grown out of it....so to speak. Dreams are hard to give up. If I had a good spot to put it, I'd be looking for a nice armoire...just because I like those. But I realize it won't fit my house or my lifestyle any more.

Sorry that I got too intense. I noticed that Nick wasn't engaging with any comments that seemed personal or critical, and I imagined that could be because he was feeling marginalized. Probably wild imagination on my part! I've noticed that many (possibly the majority) of OPs mention resale when they are considering making a change in their home's function, but often the resale is not imminent. If the sale is a decade or more in the future then it doesn't matter what future buyers might think, to me anyway. Only Nick and his household can know if this amount of dining space is sufficient for them. My reading of the original post was "we want to make this change because it would work well for our household, but we are worried about what hypothetical future buyers will think." Maybe I'm reading too much into all of it! Again, sorry for the drama :)

RL is wrong and right. There IS a window eliminated in the bedroom since there's only one exterior wall, but by all means the master should be on the other side, with windows on the back AND side. Simply flipping the master with the other two bedrooms will result in a much better plan: quieter and further from the garage and kitchen/laundry noise. There are other aspects of the plan which could also be improved. Perhaps it's not too late to bring in an architect

Hi TIffany, first let me say how sorry I am you had to go through the fire and then get Covid, not to mention the gypsy-life. I'm glad you came through it with so much drive and enthusiasm. A lot of people would have just given up. So, you will have a dining room in that room. One of the things you could do to bring in more light is to have some lovely built-ins constructed (don't know your style) facing the window with mirrored doors and maybe a mix of clear glass as well to house your dishes, trays and ornaments. I assume you will have a chandelier (light!) and possibly some down lighting or spot lighting. I saw an interesting dining room, though I doubt this is your style, but they painted the ceiling a metallic gold. It was fairly muted but it reflected whatever light was in the room in a subtle way. I saw another application where the designer created a coffered ceiling but instead of paint the little squares were mirrored. It was lovely because in daylight it picked up the green of the outdoors and cast it about the room. You could also hang pictures with picture lighting on top, paint the room a fairly deep rich color and have the pictures pop that way. You might be able to do all of the above if you're careful. Also, could you modify the window and have a glass canopy at a 90 degree angle extend out above it so that even more light will enter. Alternatively you could put in a small bay window there which might bring in more light. Not sure what you're going for in terms of style.