Where are doors? Exterior doors? There has to be 2 of them minimum.

Yes the layout is a bit odd. Reminds me a bit of the New York City Subway apartments.

Keep in mind that a typical island is 3' wide. That could eat up a lot of dining room space. Depending on how you laid it out.

I actually think turning the living room into a bedroom would work. Right now the living room is on the opposite side from the kitchen/dining, which is awkward. Having all "public" space together makes more sense.

So knock down the walls between kitchen/dining and dining/bedroom 2. Create one combination living/dining/kitchen. How often do you have guests for dining? Could you turn the area to the right of the kitchen into a breakfast nook, do most of your eating there. And you could put up another table in the combined dining/living when you do have guests.

Since the living room is larger, with a fireplace, I'd be tempted to turn that into the master bed room. Which is why I wonder about doors. Is there a place to stick a powder room on that end so the mbr would at least have a nearby toilet for middle of night bathroom runs.

Here's the layout again with the doors and windows marked. The purple boxes next to the windows are cast iron radiators which are somewhat of a layout constraint.

The area to the right of the kitchen is currently a breakfast nook, but it's really the only space available for a powder room/pantry.

The plan was for the island to be 6' long by 3' wide, with a foot of that being bar seating (essentially 1 row of 24" deep cabinets and a 12" overhang. By my calculations, the overhang would take away about 9" from the dining room.

The main concern with doing a combined living/dining/kitchen area is whether or not the space is large enough.

We expect to be have friends over often enough (5-6 people every 2 weeks or so) with probably less than a dozen big gatherings (20+ people... I have a large family) a year.

Thanks for your help!

I'd be inclined to do something a bit more drastic. Like bring the kitchen and dining room up to the LR and put the bedrooms in the back.

So old kitchen + DR --> 2 bedrooms
and LR + BR 1 + BR 2--> LR + DR + kitchen
You could put the powder room and laundry room in that nook at the far end by the back door, so you'd still have a hallway going that way.

Of course, I don't know how interested you are (or how much financial sense it makes) to do that drastic of a change. But it would make the flow more sensible. And you could capture the front portion of the hall into the adjacent rooms, giving you more usable square footage.

Though switching around the layout like that would be ideal, it's out of our budget. The rear portion of the house has an unfinished basement, so we're able to make plumbing and electrical changes relatively easily. Any changes to the front area would require demo'ing parts of the finished portion of the basement.

Is there a bathroom in the basement? I'm not sure I would add a powder room, since you already have a bathroom on the main floor.

Is your main family entrance in the front or back? Are there coat closets at both ends? That would be my priority.

I like the idea of turning the LR into a bedroom.

There is no bathroom in the basement, which is used more as a laundry and bonus area.

The main entrance will be in the front. Currently, coats are hung in a nook facing the stairs heading to the basement, which is really as close as you can get to the front door and works well enough.

I suppose we could leave the breakfast nook as is for the moment and reconsider whether we want to convert it into a powder room/pantry at a later time. The main reason for wanting a powder room is to have somewhere to direct guests without them seeing the (very likely messy) main bath.

My main concern is whether or not the combined living room/dining room will be big enough. The total length of both rooms will probably end up at around 20'.

What is the closed-off space next to the front vestibule?

if you cant move the kitchen/dr/lr to the front of the house, can you move the entrance to the area between the stairs and the closet, with a sidewalk leading up to it? I really wouldnt want a ma bedroom next to the entrance.

The closed off space is the stairs leading up to the upstairs unit (duplex).

As for the side entrance, this is not possible either. The house is a semi detached duplex so the entire right side of the layout is a common wall.

I'd take out the wall between kitchen and dining, make a large L shaped run of cabinets (back wall over to back facing door, left side wall up toward front as far as you want to take the run) with a large island running front to back axis with a dining section toward the front of the house on the end of the island. So you have only one "table and chairs" instead of two (kitchen set, dining room set). Use the corner in back right for storage/pantry/mudroom/washer/dryer/scullery. Or, if you want separate eating table, don't put dining real estate into island, shorten island, and put a built-in banquette bordering the wall of bedroom 2 and that corridor entering the kitchen.

Both would give you a big, roomy feel yet homey space with a lot of function, and a lot more light since now your light is coming from two sides and is not blocked by the wall in the space.

Option one concept sketch (details of layout TBD, this is conceptual only):

Here's the other concept: