Just east of Santa Barbara, Montecito’s eight square miles are flush with lavish estates, luxe compounds, and secluded manors. Affluent families and individuals—including a smattering of mega-celebrities like long-time resident Oprah Winfrey—call this seaside sanctum home.

Built into the oak- and eucalyptus-laden foothills of the Santa Ynez mountains (Montecito means “little mountain” in Spanish).

The peaceful town boasts several world-class resorts, top-of-the-line schools, country clubs, and a selection of high-end shops and restaurants.