Having owned in Winni, and currently on Newfound, I can tell you that you'll get more bang for your buck by way of size and value on Winni. Although, in my opinion Newfound is a more desirable lake to own on because of the water quality and the absence of 40' offshore boats and cabin cruisers. Most of the craft operating on the water are owners and aren't trailering their boats on the weekend. To me, it seems to bring a level of accountability, respect, and stewardship to the area that I didn't find on Winni. Real estate on the big lake is more plentiful and you'll find that you can get into a waterfront property at a reasonable price. On Newfound, anything directly on the water that doesn't require crossing a street is gonna start at $400k, and it's going to be a cabin with a holding tank, minimal shoreline, a very small beach (if any at all), and a very small lot. There are some co-ops, associations, an cabin communities that will cost less, but for their price you could own independently on Winni. I mention this because you stated that Winni may be above your price range. I assure you that Newfound is more expensive for what you get. I'm not as familiar with Winnisquam.
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