Defintely a pricey area of the state to move into... But with your budget, you shouldnt have an issue.
thats the order of highest class, with fairfield being the highest.
With that being said, there are nothing wrong wtih the other two towns, and they are still full of money. lol
There are some nice condos in milford that are on the beach.... A little bit of googling can likely find them - take a look at those.
Im not a huge fan of that area of the state along the 95 corridor... They are encapsulated into their own little world down there. Attitude wise, and travelwise. Traffic is intense. The are all however close to route 8.
Not sure why you are moving, or what you need to be close to - but if you want to be a little more removed from that area, but still only 10-15 min away... Try shelton. A bit more country, but the town itself has really come along way. The further up the route 8 corridor, the more hit or miss it will become until you go north of waterbury.