One of the first step will be going to the city office and found out exactly what are you permitted to do in your area before you even start making any kind of plans. This is the right place to make your mind if is a good idea to do a complete restoration or a complete demolition.
Best of Luck,
Is there a lot coverage which restricts what you can replace it with?
Are there conservation issues to look at?
Is what you are building reasonable for the neighborhood - style, cost, etc. ?
Does your lawyer see any other issues? association approval, health department (septic), easements, ...
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I will assume that you are looking to keep the existing home and make the components new. New kitchen, new bath, new insulation, updated wiring, new roof, new windows, new heat and a/c, redo floors, paint and re-landscape.
None of these are a problem and easy to do. The more costly issue becomes if you want to change the size of rooms, room layouts, possible expansion etc and bring everything down to the studs.
Also what would be of importance is that the completed project is in keeping with the value of homes in the market for the location, unless you don't care.
I am happy to meet with you to discuss your expectations and options. I am presenlty building some homes in Newton and just completed one in Brookline.
Contractors can answer the question of rebuilding process and permits. Architects and Designers can answer question about permits and drawings. Realtors can help you navigate and stir in the right direction whatever path you will choose. When you ask clear and specific questions you'll get a lot of good responses.
If you are talking about just rehabbing what is there, talk to a contractor and a designer to see what can be done to satisfy your wants and needs.