I'd like to chime in on this because I did quite a bit of looking around before we bought and still continue to as eventually I may want to upgrade some from where I am at now. I own in West Wardsboro, tucked in between Mount Snow and Stratton. Great, great place for ski country. Those two mountains, plus Magic is a great little mountain with awesome vibe and tough terrain, Bromley is in ear-shot (30 minutes), and Okemo and Killington are easy day-trips under an hour. Just some observations that others may have mentioned as well, but adding what I can:
-The Stratton area over say 1,500 feet does very well. I'd want to be in that range or over that. I'm around 1,800 up. We get about 125" a year and do ok with retention, great with coastals that hug a bit, and various other events.
-VT definitely has varied snow over short areas based on elevation and proximity in the spine.
-Areas like Townshend, Jamaica, Manchester when you get down in the 700-1000 ft range are noticeable less snowy. Great towns, still plenty of snow but not as much.
-The SVT ski areas have some pretty great towns though, Dover, Ludlow, areas of Wilmington etc are pretty cool quintessential VT towns. Think of it as a mix of farms and mountains, red barns and log cabins, good food and good amenities. Close skiing. There are also many homes in the reasonably affordable range. Properties can be had with 10-30 acres. Once you get on that higher range of land there are not as many as say the NEK of VT or ME.
-As others have said the Searsburg area just south of Wilmington is a high elevation snow magnet. In general though, if looking Southern Greens, try to stay over 1,500 ft. So many good homes available though in the $175,000-$300,000 range. Many too that are way higher and upscale, like the Stratton, Hermitage, Manchester, Dorset area. I got lucky to buy my small log cabin for $109,500, they needed to let it go and it needed some TLC. We've really brought it back and my brothers and I and kids spend a good 50-75 nights a year there.
-Some great summer stuff down south here too, lot of falls, Dorset Quarry we jump at all summer, but still it's a relatively quiet place. More New Yorkers than Mass, easier travel from the south than to areas in NVT, NH or ME. Anytime you can come from the NJ/NY area via the NY Thruway you are doing better than through CT and MASS.
-I've looked around the Mad River area and further up through Waterbury to Stowe. What I've found is more limited real estate, more expensive, less land. I wanted to be in the area, just a little more snow up there and intense winter weather, while still those great ski town vibes. It also has the added value of proximity to Burlington if you want to take in a summer day on the lake, a more small city restaurant and bar feel, college town, catch a UVM hockey game or minor league baseball game. Healthcare there is the best in VT. But I've really struggled to find the right mix of real estate offerings at a good price there with some land etc. than I found in the Stratton area. It's a little more congested up through that area (not so much traffic but just tighter land), and the Warren, Waitsfield, Waterbury, Stowe real estate markets are tough. You just won't find that many appealing mountain type cabins or homes with land at a square price. Many of the homes seem more residential to me, a lot of bedroom type areas catering to the Burlington area, or high-priced Stowe real estate. With that said, it's got a lot to offer and a great winter climate. The skiing from Sugarbush to MRG, Bolton, Stowe is tough to beat.
-That stretch from Killington east to Woodstock obviously has a lot of old world VT appeal, but it just never was my favorite. I find the Killington area kind of bland, and Woodstock and east elevation drops down into the CT River and as it does so does the snow.
-Burke is a growing hotspot in VT but I find hanging my hat on skiing Burke Mtn with its poor lift and infrastructure and reliance on natural snow etc, tough. Cool place, plenty of land to be found there and some cool cabins, camps and mountain homes, but it's sort of an island for me not worth driving that far for. There is not enough skiing en mass there, it seems everything is always 90 minutes away.
-Lastly for VT, I've spent some good time in the NEK. From Jay through Lake Willoughby east, it certainly does have a different "North Woods" feel there. Many more evergreens, the hardwoods drop off, it's cold, snow retention is high. But it's desolate and far. Sure Jay gets a ton of snow, just be careful away from mtn as elevation drops off to the east and west as the snowfall plummets. My buddy lives in Maidstone, real estate pretty cheap and lots of land, but its far from a lot of ski variety. I'd probably only live up there if I were going to be specific to the Jay area and have elevation. Maybe SW of Jay with chances for trips to Stowe too, but cheaper real estate and land, but elevation will be needed.
-Don't go anywhere near Bennington or Brattleboro, no elevation, snow holes. They are nice towns, but may as well live in an Albany suburb or Saratoga. When you hit the Bennington Bypass and start heading north into Searsburg pass you'll see what elevation does and getting into true snow country.
-I'll only comment on NH in that I've looked a lot, but have not been thrilled with my selection. I actually looked at that house in Randolph someone posted. Great spot, shadows of the Presidentials. The Presidentials are obviously without equal in regards to being impressive views. I've just not found as much charm in NH, it seems more congested on the roads, the motorcycles, lots of tourists in the summer cramming through Franconia and other areas. The skiing is good, but not as good as VT. What NH does better is lakes and views. If you are looking perhaps for a dual summer/lake and winter adventure home, and you've got some money and willing to take on CT and MASS driving routes, NH has a great number of lakes and year-round potential. It's just that the southern half of NH is more like Mass or NJ than I'd like. One thing I have found in NH are quality homes in the mountains at pretty decent prices. More of a selection with land than you would find in the Mad River Valley or Stowe area. Similar to the Southern Greens.
I am going to leave Maine to the experts, it's just too far for me right now until maybe some point later in a much slower life. I'll leave you with this though, drive and proximity matter a lot. A three to four hour drive is a lot more doable than a six hour, a six hour drive that becomes hey maybe we should look 7 or 8 hours really becomes functionally deficient for a weekender or family. Later in life, a more full-time commitment, sure, further north works. It's just that second-home owners really need to consider the drive time and route, stress and use when rounding out the whole equation. It matters because what good is a cool place if you can't get there.
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