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Originally Posted by toddb
Besides Stratfield, you can also look into the Fairfield Woods section (closer to Black Rock Tpke) - there's plenty of housing in that price range, and you'll get more than a cape for that price. Like Jay said, your kids will be safe and in good schools pretty much anywhere in Fairfield. I would definitely drive the area, and even walk around a little bit, particularly on the weekends, if you have the time.
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That's a nice section too. The big difference between there and Stratfield is that Fairfield Woods tends to be mostly postwar houses, while Stratfield is older and is comprised of mostly prewar houses. It's all a matter of taste. I'd say the overall housing stock in Stratfield has a broader range of sizes, prices and styles, from small, side-hall colonials to larger colonials, some Meditteranean style houses, and even some very modern houses. Fairfield Woods is mainly mid-sized postwar splits and colonials, with a few older victorians thrown in.
As an earlier poster said, you need to visit the neighborhoods and see for yourself.
Lake Hills, mentioned by JayCT, is also a really nice area. It is also mainly postwar houses, with some nice colonials as well as some ranches. There are some houses there that were originally vacation homes that have been converted to full-time residences, but there are also some higher-end houses, especially off Morehouse Highway and Tahmore Drive closer to the lake.