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The Exceptionally Expensive Estates of Lyford Cay, Bahamas

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One of the Caribbean's most exclusive enclaves, Lyford Cay has been the winter home of many celebrities, titans of industry, and royal gadabouts since the '60s. President Kennedy hosted the British Prime Minister in the gated Bahamian community in 1962. The Greek shipping magnate Stavros Niarchos was a frequent visitor. With well-bred names like that attached, it is no wonder that prices at Lyford remain sky high, stratospheric even. The Point House, located on a rocky promontory just yards from the surf, is a 3.4-acre, six-bedroom estate asking $35M. For that mountain of cash, the next owner gets both bay and sea views, a boat house, guest pavilion, and an ever-so-old-school grass tennis court.

? The aptly-named Winter Dream is a doozy: 8-acres of waterfront topped with a 12,000-square-foot main house, a 5,100-square-foot staff residence, and two guest houses. The listing claims the property is self-sufficient, with power generation and rainwater collection systems, which is all well and good, but perhaps the current owners were a bit too practical with their interior design. For the $39.5M asking price, we're guessing buyers will be looking for more than '80s-style prints.

? The Yellow House is yet another Lyford property with an asking price above $30M—$36M to be exact—but unlike the previous two, this sprawling estate has a sales contract signed. The beachfront estate, with five manicured acres overlooking the sea and luxe interiors, won't be sitting vacant for long and with three bedrooms dedicated to household staff, there should be plenty of maids and butlers to keep this place shipshape.

? Set inland and thus lacking the waterviews of the island's most prestigious estates, La Paloma still has its virtues, including easy access to the renowned golf course at the Lyford Cay Club. With a simple, columned form, the house contains 4,000-square-feet of living space and three bedrooms for a tenth the price of some of the larger properties we've seen: $3.95M.

? If Lyford Cay was a baseball stadium, the Sunnyside condos would be the cheap seats, but they'll still run $1.75M for a two bedroom. Luckily, for that price, the buyer gets a sized-down version of one of the island's impressive villas: a trellised outdoor space, luxury interior finishes, and a (shared) swimming pool.

· Point House [Sotheby's]
· Winter Dream [Sotheby's]
· Yellow House [Sotheby's]
· La Paloma [Sotheby's]
· Sunnyside [Sotheby's]