Alas, this “bonus room” looks très Cravath 2008 (especially with the antique telephone and dated Dell laptop in the corner):
We can carp about the interior, which clearly requires refurbishing, but we have no cavil with the outdoor spaces, which are impressive.

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As noted in the listing, the house sits on a “double landscaped lot with pond and gracious garden,” replete with “three decks plus a beautiful brick patio.” Here are the photos, which reveal the skyline view:

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And don’t forget that Lake Michigan and the beach are just a short stroll away.
So what’s our summary judgment on Frederick Winston’s former residence? It’s a beautiful old house, with ample square footage — 10,000 in total, per Redfin — and great bones. The location and the landscaped lot are superb as well.
The downside: this is clearly a fixer-upper. Compare it to a prior Lawyerly Lair in the Windy City, former Northwestern Law dean David Van Zandt’s Lincoln Park townhouse. Dean Van Zandt’s house was significantly smaller, with a mere 6,300 square feet, but it was in much better condition and had a much lower asking price (and ultimately sold for well below ask).
So whoever buys the house that Winston built will probably have to pour a seven-figure sum into renovations. But if you’re buying a house for ten million dollars, what’s another one or two?
UPDATE (12/16/2012, 4:45 PM): Thanks to Some Queer for drawing our attention to the listing.
1508 North State Parkway [Prudential Rubloff Properties]
1508 North State Parkway [Redfin]
Earlier: Lawyerly Lairs: Dean Van Zandt’s Delicious Listing
Lawyerly Lairs Update: Ex-Northwestern Law Dean Sells Magnificent Mansion