Connecticut

That's about 20 minutes from Milford.

You can find 2 bedroom apartments there for your price range. Be advised that the apartment will most likely be in an old Victorian converted into 2 or 3 apartments.

However, Fairfield Avenue in Black Rock has a fair amount of bars, clubs, restraunts, shops, etc. that are trendy. Lots of young up-and-coming professionals live around there, and it's pretty near a nice sound-side park called "Saint Mary's by the Sea".

Avoid living too close to Fairfield Ave, though... a lot of those young professionals drive choppers at ungodly hours on the weekend.

Bridgeport as a hole is a gritty city, but neighboring Fairfield is a pretty affluent place, and Milford itself has tons of shopping. They just built a new commuter train station in Fairfield right at the city line with Black Rock, so you'd have walkable or bike-able access to it.