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For good weather it may be necessary to stretch the drive times to one of the cities.
I don't the the OP has a requirement to walk to TJs - so that opens up a lot of neighborhoods in Pgh.
But now I'm thinking of the West Hills neighborhood in Knoxville just across the interstate from TJs. Miles and miles of greenway with a great elementary school, parks, YMCA, etc. Easily within range of Chicago and the money they'd save would pay for a lot of plane tickets to Boston.
Looking for a city or town anywhere within 12 hour drive of both Boston and Chicago (so, the Eastern part of the US) that is somewhat progressive and offers a few "basic" amenities: large-ish airport within an hour, Trader Joe's and Whole Foods Market (or similar--this is due to personal preference as well due to food allergies; these stores make our lives easier in that respect), good public schools and parks, and a decent amount of walkability. Sidewalks are key to our version of walkability. It's not necessary to be able to walk to something (though that would be terrific) but we regularly walk/run 2-3 miles a day and it's nice to be able to do that from the front door. Sidewalks through connecting neighborhoods or hike/bike trails that are safe would work for us.
We can live anywhere, though milder weather is preferred. That's why Portland, ME is off the list.
We work from home so we can live anywhere (within the above parameters). Commuting is not an issue, but we know that some large cities have congestion day and night. It would be great if elementary schools are within walking distance.
Budget is under 550k for a 2500-3000 sq ft house.
Your criteria in my opinion (especially with a desire for milder weather) points toward the Southeast US and would second Durham/Chapel Hill or Winston Salem as excellent options. Both are quite affordable yet progressive cities close to airports, with access to very good public schools, lots of parks/greenspace in close proximity, a heavy presence of TJ's/WF/other natural foods grocers/Farmers Markets/coops, and a significant number of walkable (and desirable) in-town neighborhoods.
Look into the bigger Upstate NY cities(Buffalo, Rochester, Syracuse and Albany) or perhaps Cleveland, but weather may be an issue. If want specific NY communities, let me know.
Keep in mind with the NY areas, except for the Albany area, you have Wegmans as a grocery store option. Many of the smaller cities in between have a Wegmans as well(Ithaca, Corning, Geneva, Auburn, Canandaigua, Batavia, Binghamton(Johnson City), Elmira, Fredonia, etc.).
I believe that all of the bigger Upstate NY areas now have a Trader Joe's as well.
Just to add to this, Albany also has a Whole Foods in Colonie where Trader Joe's is located. Rochester(Brighton) and Buffalo(Amherst) are getting a Whole Foods in the near future. Brighton and Amherst has neighborhoods that would fit much of the criteria as well. In the Syracuse area, the DeWittshire area of DeWitt(Jamesville-DeWitt Schools, close to TJ's and one of the biggest Wegmans in the chain) could work and sleeper could be the village of Liverpool due to having an elementary/middle school and a great, big park there: Onondaga Lake Park » Onondaga County Parks Brockport in the Rochester area, Ithaca's Fall Creek area, Geneva's western half and a few others could work as well.
Last edited by ckhthankgod; 07-04-2015 at 09:04 AM..
Up to 12 hours driving from BOS/CHI, with a trader joes, mild weather, and generally meeting the rest of your requirements:
Richmond, VA
Winston-Salem, NC
Raleigh-Durham, NC
All good choices. Specifically within the RDU area, Cary would fit the bill. Excellent greenway network. Good schools. Lots of great homes well under the OP's budget and very close to RDU airport. Drive time may be over 12 to Chicago, though.
State College, PA - well, except for the airport part of the criteria...
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