As a licensed broker, I can't really address lifestyle potential that one area might have vs another. I can say that I've got a listing that might be appealing in that it meets your location criteria in that it's less than 2 hrs to NYC and the bonus is it's less than 1.5hrs to Boston also. Pachaug Pond is the 2nd largest lake in CT. The yard is private and you can't see another home from the back or front yard. This property has deeded lake rights but is not waterfront, so you save on taxes and purchase price and yet have the lake access via community beach, dock and pick nick area (accessable via walking trail or car)
Working with a REALTOR who's got your interests first is your best bet as they can search what's available based on search criteria like location, size, age of home, characteristic (water view, waterfront, etc) and they have the skills to negotiate on your behalf. http://realtormag.realtor.org/sales-and-marketing/handouts-f
Hope this info helps.
Greg Hanner, Broker, REALTOR, e-PRO
Greg is correct... as licensed realtors, we can not "steer" you toward a specific town/community.
You might contact g/l/b/t organizations in Dutchess and Litchfield Counties, both within a 2 hour drive of New York City. You might also choose to work with a gay or gay-friendly realtor, who can introduce you to properties in these counties.
Good luck in your search!
Associate Broker, Massachusetts, New York, and Connecticut
Berkshire Property Agents
12 Railroad Street
Great Barrington, Massachusetts 01230