Be sure to check out Pomfret/Northeeast CT and Chester/Essex, CT River Vaalley
Madison --
I posted this for someone who is looking to come here from Colorado but it may be applicable to your situation as well.
Pomfret/Woodstock area is as beautiful as any area in the State, really as nice as most anywhere in New England.
It's in the northeastern corner of Connecticut, known as "The Quiet Corner", a rural area with a combined population (Pomfret, Woodstock, Eastford and Brooklyn) of 20,000. Centrally located between Hartford, Providence RI and Worcester, MA (50-60 minute commute to any of the 3) and only 90 minutes to Boston (longer in rush hour traffic)
A large percentage of residents are college graduates in professional and business careers. Many homes in the area are colonial or farm house style; stonewalls, barns, and trees line the roads and highways. There are no real mountains, but plenty of rolling hills, beautiful farms and the area is steeped in New England history. In the fall the foliage is breathtaking, as good as Vermont.
This area although very rural in nature, is very accesible and fairly easy drive to Southern CT (beaches/boating/seafood) and points north due to I-395 which is a major interstate running South/North and bisecting Eastern Ct.
Restored older homes and farmhouses in that area start at 350-400K. There are some really nice older farms with acreage that come on the market from time to time, these will start at around 500K.
Schools in that area are some of the best in the state, with Woodstock Academy (regional) high school serving the 4 towns mentioned above. This is an excellent high school with highly rated academics and a well funded athletics program.
Other areas in CT to check out --
Litchfield County is the Northwest corner of the state, every bit as beautiful as the Northeast Corner EXCEPT:
1. You will experience more snowfall due to storms that tend to track eastward through the Hudson River Valley in NY, then UP through the Berkshire mountains, then UP through Vermont. These storms typically dump more snow on the Northwestern Corner of CT with smaller deposits in the Eastern half of the state. (Large amounts of snow in Eastern Ct are just not happening like 40-50 years ago, an occaisional nor'easter will hit the area but more times than not it ends up being a "rain event" as opposed to snow).
2. Litchfield County is more densely populated, more "touristy", being in close proximity to New York City many of the tourists are from New York and New Jersey (not that there's anything wrong with that). However the money imported by Wall Street brokers, investement bankers, high powered attorneys and celebrities have driven real estate out of reach for the common man.
3. This is my opinion and my opinion only (I'll no doubt get slammed for it), but the NYC influence is not necessarily a desirable influence, unless you enjoy spending mucho $$ at trendy local breakfast spots with the limousine liberals (and numerous celebrity residents) leisurely feasting on eggs benedict and reading the Sunday [NY] Times. Personally I prefer dining with the "swamp yankees" or more traditional old time New Englanders you find as you travel towards the Northeast corner of CT. Sure they're rude and crude dressed in their manure stained overalls, but they spin a great yarn and never pay more than a couple of bucks for a nice farm fresh Sunday breakdfast. You get the picture.
FInal Recommendation Essex, Deep River, Chester, East Haddam, Old Lyme (Ct River Valley) --
This is another beautiful area of the state and real estate here (it's the area I live in) was out of sight a year or two ago but has returned to earth recently. Lots of older homes and plenty of "fixer-uppers" It's comparable in price to the Pomfret/Woodstock area not quite as rural and hilly, not quite as many farms, but if you want to live close to the water this area is preferable to both the Northwest and Northeast corners.
The CT River is beautiful and it iempties into Long Island Sound, which is a stones throw away from the Atlantic ocean. Some of the best boating and fishing in all of New England is in this area. Good seafood restaurants, plenty of things to do in or around the water.
The school system for Chester, Deep River and Essex is comprised as follows -- Each town has it's own elementary school with John Winthrop Middle School and Valley Regional High School serving the combined student population. If you GOOGLE John Winthrop Middle School you will get plenty of hits including the District 4 websites for all the schools + Ct Ed Websites with ratings, test scores, school demographics, etc.
All in all it's a great area to raise kids.
SUMMARY - Frankly if I didn't care about being close to the water I would prefer to live in the Pomfret/Woodstock area. But I love being near the water, I've got teen aged kids who I would not uproot at this point, and it would add 20-30 minutes to my commute (each way), with the price of gas hovering at 3.10/gallon I'm not moving further away from my office.
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