There are plenty of places in CT where you can get a decent 2BR for $1100, be walking distance from a Metro North station, and have less than a 2 hr commute.
3 hours is Albany. I pay about $800/mo for a 4b/3ba house there. When I used to be on the Amtrak a lot there was a fair number of folks doing that commute, mostly lawyers and construction guys.
90 minutes is Rhinebeck/Poughkeepsie. Plenty of country and suburbia places for $1100.