1. Chicago This five-bedroom brick-and-limestone home was built just five years ago and features three decks, a heated three-car garage, and a penthouse-level sitting room with wet bar. $3,200,000. Kimberly Gleeson, Koenig & Strey Real Living/Christie’s Great Estates, (312) 893-3586
2. Leesburg, Va. This five-bedroom home, built in 1988, sits on a 32-acre property that includes fenced paddocks and a pool with a 30-mile view. The interior is appointed with heart pine floors, a walnut staircase, and a mahogany paneled library. $4,500,000. Andy Stevens, Long & Fosters/Christie’s Great Estates, (540) 687-8530
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