Hip, urban neighborhoods in Sarasota Fl.

Downtown tends to be mostly condos or more expensive homes. There are some good deals, but you are likely sacrificing a nicer home for one closer to downtown area. For "hipper" areas, I recommend looking at Gulf Gate Estates, Southgate, and around Hillview St. Each of these has cool nearby amenities (bars, restaurants, etc.) and you can get a better value:quality out of your home.

Gulf Gate Estates is a cool area, funky shops and restaurants. Pretty close to downtown.

Indian Beach/Sapphire Shores is where the younger crowd usually lives. Close to a few colleges. Siesta Key is pretty laid back too, you might look into here more than Indian Beach.