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Since you mentioned that you would be willing to consider private schools I would suggest look in the Northwest Section of Philadelphia. Specially look at West Germantown, Mt. Airy, and East Falls. You could easily find a very large Victoria or other historical house in your budget. The private schools are excellent. The public schools are horrible. Mt. Airy and East Falls have great little downtown areas.
If they did, they are wrong, as Upstate NY is definitely Northeastern. It isn't necessarily Northeastern in the stereotypical Bos-Wash corridor way that people think of the Northeast, but it is Northeastern. Plus, its proximity to the Bos-Wash corridor, as well as major Canadian areas allows for potential day trips to these areas using multiple modes of transportation.
I'm also curious if the OP is open to sections of a city that offer the type of neighborhoods they are looking for? If so, other Upstate NY areas that come to mind are North Buffalo around Hertel Ave, Buffalo's Elmwood Village, the Southeastern Quadrant of Rochester, Delaware Ave/Whitehall/Pine Hills in Albany, Upper Union Ave in Schenectady, Troy south and east of RPI, Binghamton's West(south of Main) and SW sides and South Utica(south of Parkway/Burrstone Rd). All have private schools within/near those city neighborhoods with SFH's and with business districts/Downtowns nearby.
I will say that Lakewood or Royal Oak outside of Detroit would also be good choices.
There's plenty of areas in and around Pittsburgh that could work, insofar as there are still large, beautiful Victorians available at the price point you're considering.
The classic upscale "urban suburbs" are Mount Lebanon, Aspinwall, and Sewickley - all of which are affordable at that price point, although some of the larger fully updated houses would be out of your range. Other walkable suburbs which are on the upswing, but don't have as tony of a reputation (e.g., more blue collar, but gentrifying a bit, and very walkable downtown) are Dormont and Carnegie. Or somewhere like Edgewood, which has the social qualities you're looking for, but lacks decent neighborhood public schools.
Going the "city" route isn't impossible for parents here too, as there are many "streetcar suburb" type neighborhoods within city limits which are very similar to where you now live in Brooklyn. There is a public school catchment within the City (covering Shadyside and parts of Squirrel Hill and Point Breeze) which is very good. Houses here are expensive, but similar to the top-notch suburbs, you could afford something, just not exactly what you wanted. There's also a robust magnet school system, and of course private schools.
if you could get over the anti-Midwest thing....I'd say Evanston Illinois fits your bill perfectly. progressive educated, home to Northwestern University...right on Lake Michigan with its own city beaches, definitely has maintained its own edge, connected to Chicago via both the El and Metra, very urban, walkable, bike able (I believe Chicago's Divvy bike sharing program is extending into Evanston) with an INCREDIBLE a housing stock..
I think what this thread shows is that just about everywhere has versions of Ditmas Park. It is a very common housing type in older cities and their older suburbs. It's just not so typical of Brooklyn, which is much denser than most places, and where the characteristic landscape is the brownstone street. Hardly anyplace has brownstones like Brooklyn but nearly everyplace has its Ditmas Parks, and many of them considerably nicer than the Brooklyn version, from Summit Avenue in St Paul to Evanston Ill to Shaker Hgts/Cleveland Heights to Pittsburgh and Buffalo, Mt Airy in Philadelphia, and on and on.
How are Chicago's 'burbs? People who live in the 'burbs are like people who live in urban Chicago? I thin that Washington have urban suburbs, but I'm not sure.
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