have you thought about adding a second floor to your house?

Getting a roof line that will work with that footprint will be a challenge. I can’t read all the dimensions so can’t offer any ideas.

Yes, going 'up' might make more sense. Sometimes...if the addition dwarfs the house...you are money and trouble ahead to raze and start fresh, or go down to the studs and reconfigure the entire space.

Get a pro in to check and see if the structure has the power to hold up a second story. If it can be made to support the build you could do a dormer extension like this on both front and back if you need it.

Old Hill House · More Info

The house is 1 1/2 story. we really need a larger living room on main level the roof line is my biggest concern and I’m out of ideas

the dimensions of the house are 30ft x 30ft

I would put a front facing gable on the living room addition and continue the roof line back to cover the office/study.
If there is a side window on the second floor above the new office, you will need to move it, replace it or miss it with the new roof. More pictures and dimensions for the addition would be helpful.

That is a teardown and do a new build. Any adding on to it will be way more than you paid for it, and won’t fix the numerous issues that the orginal structure has. So either do the teardown, or sell and move to the bigger house that you want. Or learn to love what you have.

Ignore verbo. He tears down everything and he thinks he knows everyone’s financial situation.

Depending on your budget, Verbo is correct. Additions per sq ft cost up to double the cost to build new. The changes you are hoping to make would be well over 150k with builder grade finishes in my neck of the woods. What is your budget?

What is your budget? Are you in a low or high cost of living area?

Will local setback regulations allow you to extend sideways?

Here's a link to a house with a full length porch. The character you are looking for is added with much more substantial finishes, including windows, than your house currently has.

https://www.familyhomeplans.com/plan_details.cfm?PlanNumber=77416&OrderCode=GOEXP&gclid=EAIaIQobChMIobjL8sGq9wIVpCCtBh1dRAZ5EAQYBiABEgIYuPD_BwE