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I am going to be working in Stamford CT but the places that I've found in the area are a little out of my price range. So as part of my research I am looking at moving to Westchester county and commuting to Stamford.
Unfortunately I am not familiar with the area, so I am looking for any advice as to where would be a good place to look with easy access to highway or rail with rentals less than $1500/mth.
In Westchester, $1500 can be a difficult price point, since many communities such as White Plains start around this range. Check into parts of New Rochelle and Port Chester. Not all of those areas are as nice as surrounding towns, but there are pockets in each that are up and coming, so you might find something. Neither is that terrible a distance to Stamford, but 95 can be congested.
Further into Westchester, you could look at Mount Kisco, Hartsdale, or Pleasantville, though most of the rentals will be above this price point, but some might exist below it.
Within Connecticut, you could check into Norwalk, which is not as expensive as other areas, though parts are older and not composed of newer apartments, and some areas are a little gritty. And, the best value for your budget is going to be Danbury, Connecticut, in terms of having the most selection. And, from Danbury, you have a hub for HART transportation, but the train goes to South Norwalk and then you can easily get to Stamford. This would take around an hour or so, since it's about 45-50 minutes to get to South Norwalk from Danbury.
All of these areas have train access to NYC and CT, and are situated close to major highways, but Westchester towns like Pleasantville, Hartsdale, White Plains, and Mount Kisco are on the Harlem Line trains, and the New Haven Line trains from Port Chester and New Rochelle will be easiest to get to Stamford via train.