www.iFourWinns.com

Yes, sit up room on the monty is only in the entrance, but at least you can sit up if you want. Our 282 Monty had a wetbar, and my wife loved it too.
Here is a cheesy video of a 250CR for sale. It gives you an idea of how the boat is layed out, shows cabin, mid berth, engine and boat underway.
Something to watch during this cold weather at least.

http://www.youtube.com/watch?v=I9giH_X620A

And I stumbled on this newer 248. A bit north of your target budget, but here you go anyway.

http://chicago.craigslist.org/sox/boa/3549721702.html

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One of 4 Previous (Sold) Boats:
2000 Four Winns 268 Vista

Current Boat: 2004 Chaparral 235 ssi cuddy

For that kind of money, I think I would have to go to the 268 or 258 since they have the wet bar.

The video is cheesy, but actually makes me think I could live with the height issue. I need to see one in person again.

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2006 Vista 278
First Boat:
2005 Sundowner 205
Columbus, OH