Talk to residents and you’ll hear them describe a near-magical place: broad Lake Michigan beaches, lovely tree-lined streets, cool shops that are easy to walk to, and watering holes where everyone knows your name. The list of pros goes on and on. Diversity? Check: Andersonville, in particular, has attracted many gay residents (who have remade the upper reaches of Clark Street into a hot design-store destination). Easy access to downtown? Jump on the Red Line or an express bus that will whiz you down Lake Shore Drive, the prettiest commute in the city.
If you need space, check out the Lakewood Balmoral district, with its 19th-century houses in a variety of styles—Gothic, Flemish, Queen Anne—on large lots. Housing gets cheaper by the lake and a lot more vertical. In Edgewater Beach, you’ll find the tallest high-rises north of Lincoln Park, many of them modernist. Large high-floor spreads here regularly sell for less than $350,000.