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2. Greenwich, Connecticut

List Price: $41 million
Size: Approx. 20,000 sq ft
Bedrooms: 8
Bathrooms: 18

Greenwich is known for its high quality of life, but this estate demonstrates the romantic side of the town. Situated on 18 acres of pastoral land, it features a maple-lined driveway, French doors, several outdoor terraces, gardens, a pool and even an equestrian center. The home was designed by architect Robert Lamb Hart and the interior by Mark Hampton, focusing on elegance and luxury.

Photo & Listing: Joseph Barbieri | Sotheby's Greenwich | Pickwick Plaza Brokerage