This is making me think we go all the way out to Milford or New Haven or stay where we are. Walking to school, activities, etc makes it easier to do the stuff I love ... spend time with my kiddo! If everyone else is far out it will be hard to visit with friends too.

Otherwise, we would get 25% more space and a less grungy area for the same price...but lose a lot in terms of my personal lifestyle.

Could probably switch to Yale? They have some NYU doctors in White Plains too.

Thanks. I think just saying it like it is is good. I mean... the lack of social life if you can't drive often :/
Better to depriortize it vs. just wasting time looking at something that won't work.
So maybe bump up New Haven, Norwalk.

Thanks. I'll add that back to the list with private school.

Honestly, I'm going to check these areas out since my husband is hoping for a real house like this, but I still enjoy where we live now... which is extremely walkable for elementary school, activities, lunch etc and has houses in the $1.5-$2.5M range and has access to NYU in 45 minutes. Middle school and high school get harder.

Thanks. Appreciate the details there and I can add the neighborhoods to my list. Anything in this area seems to be $1.5-$2.5M for this size house.

I'd love to walk to get a coffee or lunch. I'd love to be able to walk to school and to kid activities or community activities.Groceries have delivery and can be done with my husband on the weekend. Doctors office don't require hauling around a kid and can be done via Uber. Train is less important for me. My husband would use the train more than I would.

And laid back, not lily white would be preferred. But I have a long list, soo....

Any specific spots? Good to know :)

Re: large estates ... totally agree with you.

Good to know!

Does Westport have a downtown with a good school district/ family homes? Or is it more a large shopping type area? We'll go for a visit eventually but it'll be a trip.

There is grocery delivery and my husband can drive us on weekends. Things like kid activities are harder -- happen every day, seem to be spread out, and I want to be a part of it. Thanks for overview. : )

Yeah, this is my fear. Having a hard time finding something that is a good fit, even though my husband really wants the space.