Roxbury (pop. 2300) in southern Litchfield County is one of the most pleasant exurban towns (among many) in CT. It's far enough north to be beyond NYC commuting distance, but it's a good distance for a weekend home - and every wealthy American urban Lefty deserves his dacha.
Roxbury has plenty of old farmhouses, barns, and well-maintained horsey estates with white-painted fences, but even it has been contaminated by some grandiose new construction over the past 20 years. Marilyn Monroe lived there during her hook-up with Arthur Miller. He may have suited her for a little while, but I doubt that Roxbury, or the Roxbury Congregational Church, were her cup of tea. Not that she ever knew what she needed...
The 1850 farmhouse pictured above on 4.5 acres is asking 1.9 million. (I would be inclined to get rid of that big old Norway Spruce on the front corner. People always planted those gloomy trees too close to their houses.)
More Roxbury listings here.