Asking Price: $35,000,000
The Smith Road home is a historic one, as it was originally designed back in 1939 by architects Harold Beder and Henry O. Chapman. It’s been tastefully reimagined for 21st-century living by interior design firm Cullman and Kravis, so you get the old-world appeal without any of the rooms feeling too stuffy. It’s situated in the gated community of Belle Haven in Greenwich, an area that’s among the most sought-after locales in Connecticut for its waterfront homes and proximity to town. Inventory in Belle Haven is notoriously low, which makes Smith Road all the more splurge-worthy. The next owner will not just have access to the 8,000-square-foot main home either: The estate sits on over five private, waterfront acres, which includes a guest cottage, dock and a two-story barn.