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In the Southern Adirondacks, you can try very nice little towns like Brant Lake or Chestertown, which are right off of the Northway and pretty much an even 5 hours from Miller Place. I wouldn't say that strike me as artsy or anything, but they are nice, and they feed into the North Warren School District (Chestertown does for sure, not so sure about Brant Lake), which is one of the better ones up there. And they are just a few exits south of the High Peaks, so you have the sensation of being high up, for sure. Chestertown is 15 minutes from Gore Mountain and has a nice lake, Loon Lake, and is just south of Schroon Lake, another nice lake. You should know, however, that in that price range you are looking at local neighborhoods and not the fancier second home associations, which can get quite high in price.
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Do you know if people commute from Woodstock to Manhattan for work? Is it possible?
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I suppose there are some (you do hear about people commuting to NYC from really far-away places like Montauk or Newburgh), but I don't know how they do it. I would say it's definitely not possible if you are required to maintain a presence in your office for five days per week. Perhaps it's something you can consider (albeit with difficulty) if you telecommute on three days or so.
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On a good day with no traffic it would take about 2 hours and 15 minutes. Commuting during peak rush hour would be somewhere around three hours, and that's to the tip of Manhattan - So mid-town maybe another 20-30 minutes and downtown could be 45 plus. I think losing 6 plus hours a day would be pretty tough to say the least..
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I suppose some might drive over to Rhinecliff or Poughkeepsie (or even Wassaic?), and then take the train in to NYC? I have no idea how long the rail commute takes, though.
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So where has your Catskills search lead you thus far? Woodstock?
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Have you considered Binghamton? Although SOME of the locals don't realize how good they have it, it really does have ALOT to offer. As far as getting to LI, i can make to Flushing Queens from Binghamton in exactly 3hours. So to get to Suffolk, as long as it's not on a Friday at rush hour in the summer (Hamptons traffic), you'll be okay. Check Binghamton if you can. I personally love it here. Good Luck
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