Location: Stamford, Connecticut

Price: $18,900,000

Stamford may lack the ritzy name recognition of its bucolic neighbors Greenwich and Darien, but this island estate could put the town back on the map for deep-pocketed buyers. A three-acre private island connected to the mainland by a causeway, the compound consists of an 11-bedroom main house, a guest cottage, staff quarters, and a greenhouse. While the current kitchen and family room keep the house stuck firmly in some sort of misguided '90s "I'm so rich I can be this casual" style, the rest of the house is classic turn-of-the-century charm. Well, at least as charming as a 14,000-square-foot, $19,000,000 estate could be.

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