Price: $3.8 million

Founded in the 12th century, Castiglion Del Bosco ("Castle in the Woods") is nestled among the ruins of a medieval fortress on 4,500 rolling acres overlooking the timeless Val D'Orcia in Italy. There are 21 villas, 150 acres of vineyards, and a working winery famous for its Brunello di Montalcino wine. Each 3,000- to 6,000-square foot villa is being renovated and furnished to offer a host of luxury amenities, including a private heated swimming pool, a luxury vehicle for use during visits, and comprehensive daily hospitality and concierge services. The 120 available memberships include: Virtually unrestricted yearly time in the villas, unlimited use of all other amenities year-round, and a case of each year's vintage. Each membership is active in perpetuity and can be handed down for future generations to enjoy.