I'd recommend a Cavalier 28, but I am well biased. Got mine for your budget, in a private sale last August. Spacious for a 28 footer, and well-behaved. Needed to replace the prop (knew about that), batteries and rudder (did not know about that, but the boat had a spare rudder), UV strip on the foresail and have just reconditioned the windows (many hours and maybe $100 in parts and sealant). Next on the list is replacing the depth sounder (the old one is on the blink), followed by a thousand small jobs. Technically, it is a money-pit, but with small-ish dollar amounts and enjoyable sailing in-between.
For more information, see
www.cavalier28.com/homeGlad to see that you have "physically" looked at some boats, rather than relying on boat ads and photos. Be critical of condition, don't get a project, get a professional survey, use the fact its a buyers' market (i.e. actual price will be lower than advertised).