Montecito

 

Its name has become synonymous with wealth, but this serene seaside town isn’t at all about glitz and glamour like its Tinseltown neighbor 90 miles south (and in fact, some citizens decamp from Los Angeles to Montecito for precisely that reason). A town that neatly walks the line between sylvan and stylish, the neighborhood takes pains to remain semi-rural thanks to the active Montecito Association, which has been tasked since 1948 with maintaining its aesthetic beauty. People have been drawn to the area’s temperate weather and natural charisma since the early 1900s when neighbor Santa Barbara was in its heyday as a nationally famous health resort.

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.

 

A well-heeled crowd of CEOs, entrepreneurs, and Hollywood stars, drawn to the neighborhood’s privacy and beauty.

Montecito’s Rolodex includes luminaries like Oprah Winfrey and Ellen DeGeneres, alongside an impressive history of visitors and former residents with names like Kennedy, Rockefeller, and Carnegie. Here, millionaires and celebrities are treated like regular folks. The neighborhood is also an attractive spot for affluent retirees, with over 20% of the 10,000-odd residents over age 65. Plenty of addresses function as second homes for their jet-setting owners, too.

 

An elite locale of understated elegance sans attitude, filled with quiet streets and gated estates.

Montecito may be home to the wealthy, but it’s not at all flashy, haughty, or gaudy. Residential streets are lushly tree-lined, estate entrances discreet, and the main streets’ bars, restaurants, and shops maintain a casual, relaxed vibe.

 

The townfolk mix along beaches and the two main streets, and it’s an unspoken rule that no one makes a fuss if a famous face is spotted.

Montecito residents greet the day over french toast at Jeannine’s, a local institution known for its informally elegant breakfast fare, then wander the main thoroughfares of Coast Village Road and the Upper Village to browse boutiques like Jenni Kayne and Maison K, linger at Butterfly or Miramar Beach come midday, then wrap up their evenings with a cocktail on the terrace of the Four Seasons Biltmore Hotel.

 

There’s plenty of places to see and be seen, from the Biltmore’s Bella Vista restaurant to celeb-studded Butterfly Beach.

Locals take advantage of the distinguished Four Seasons Biltmore Hotel’s Bella Vista restaurant—which hosts a legendary Sunday brunch—and may enjoy membership to the Coral Casino Beach and Cabana Club across the street. Outdoor terrace seats at either are key for people-watching while sipping on something cool and fruity.

 

Considered the crème de la crème of Santa Barbara County real estate, even teardowns go for millions.

Though gates and greenery keep most Montecito residences hidden, these bucolic hills hold wonders. Some of the earliest residents and many celebrated names in architecture (including Frank Lloyd Wright and George Washington Smith) have built everything from English manors, Normandy castles, Italian palazzos, Mediterranean villas, Cape Cod Colonials, and marble palaces. In addition to these sprawling estates, there’s also a handful of gated communities, high-end condominiums, and even charming cottages—some of which were once staff housing for the area mansions. Lot sizes are capped at eight acres, with none less than one.

 

Sunny days, ocean breezes, beautiful scenery, and the pleasant pursuit of the high life.

With proximity to some of Santa Barbara’s most glorious beaches in the south, access to ribbon-like trails into the Santa Ynez mountains in the north, plus an array of sporting clubs, eclectic shops, and small eateries, Montecito has all the benefits of a holiday getaway with all the charm of home sweet home.