I don't understand why $400k can't get you a pretty nice home in Hyde Park. Grant it, it may need a little work but the return is well worth it. There are also great & historic properties in the 8th ward especially from 71st to 79th & South Shore Drive, Congressman Jackson and his family lives there somewhere. Also another appreciating area is from Drexel to St Lawrence 41st to 55th. In no way am I steering you, just wanna make sure you add these areas to your list. If you need any assistance with property type, area information, comparables, etc, etc, feel free to contact me @ (773) 842-6101. By the way, most sellers require that you are preapproved prior to showing their property, this ensures the seriousness of your purchase. Your banker should be able to assist you in this area. GOOD LUCK & I hope I was of some help.
We have been residents for many years in central Hyde Park within walking distance of everything, Metra, grocery stores, pharmacy, and banks and a 15 minute walk to the 57th street beach!
It seems to me that there are many housing opportunities in your price range: include large condos (with parking), newer row houses with parking. Perhaps it would good to contact realtors directly since some owners are currently not listing, but are planning to in the future.
We are very happy that new people are discovering our neighborhood. It is a wonderful place to live with a great sense of community! It is very family oriented with many opportunities for activities with children. (No, I am not a realtor ......... just a happy long term resident)
Jackson Park Highlands and South Shore are also becoming highly desirable in terms of renovations - not only due to the proximity to the lake and Loop but also due to speculation regarding the potential Olympic village location.
I hope that helps!