Luxury Market Insider: Discover The Monterey Peninsula's Coastal Lifestyles, Locations and Luxuries

Coastal windswept dunes. Dramatic granite rock outcroppings. Sugarcane white sandy beaches. A lone cypress tree overlooking the Pacific. The seaside towns of the Monterey Peninsula offer a rare combination of luxury lifestyle surrounded by a raw natural beauty powerful enough to enrich the spirit and cleanse the soul. Originally established in the early 1900’s as a retreat for the railroad barons of San Francisco, today’s Silicon Valley tech titans and Los Angeles cinematic celebs sojourn to this retreat along the Pacific described by World Golf Hall of Famer Johnny Miller as, “The greatest meeting of land and sea in the world.” (1)

The Monterey Peninsula boasts an enviable mild climate, outstanding outdoor opportunities and iconic coastal enclaves including Carmel, Pebble Beach and Big Sur, each with its own distinct luxury lifestyles and residential offerings just two hours south of the Bay area. The Luxury Division sat down with the Monterey Peninsula’s local agents to learn more about the remarkable region Clint Eastwood, Betty White and Charles Schwab have called, “Home.”

“Unlike most coastal towns, homes are not on the water. Golf courses are.”

Pebble Beach may be the most internationally recognized town on the Monterey Peninsula. Pebble Beach has seven spectacular golf courses, with its principal course among the most celebrated in the world and the site of six US Open golf tournaments. The anchor of the community is The Lodge at Pebble Beach, a landmarked hotel and clubhouse built in 1919 and perfectly positioned along the breathtaking main road 17–Mile Drive, which winds along stunning golf courses, magnificent mansions and the Pacific coastline.

3406 17 Mile Drive, Pebble Beach, CA 93953

Compass agent Mark Peterson of the Bambace Peterson Team was raised in Pebble Beach where he lives and works today, giving him intimate knowledge of the community. Mark explains, “Unlike most coastal towns, homes are not on the water. Golf courses are, and create viewsheds and open space for all to enjoy. There are just 38 oceanfront homesites in Pebble Beach, making them exceedingly scarce and the cornerstone of the Pebble Beach ultra-luxury market.” Another element adding to the prestige of owning a home in Pebble Beach is the community is mostly gated, with an entrance fee of $11.25 toll per vehicle, similar to a national park. Mark continues, “That said, The Lodge and Spanish Bay are beautiful and welcoming Pebble Beach resorts with resort-lifestyle including great recreation, restaurants and shops to be enjoyed by residents and visitors alike.”

Compass agent Michelle Hammons has lived in the Monterey Peninsula since 1990, and works with many buyers in search of luxury homes in Pebble Beach. Michelle lays out, “There are three principle determinators in the Pebble Beach luxury space: oceanfront, ocean view, and golf course view. Other factors are similar to those in any real estate market, such a space and finish level. Anything beautifully finished and move-in ready sells quickly and at a premium.” Michelle adds that buyers for these luxury homes also generally have the luxury of time. “These are most often vacation homes, so there is no pressure to buy within a certain time frame. Buyers can wait for the most desirable homes to become available and then make their move.”

“Luxury here is not about size. It is about location.”

The journey down 17-Mile Drive from Pebble Beach to Carmel-By-The-Sea is just a few miles, but it transports to a world away. Carmel-By-The-Sea is a fabled luxury beach community with a decidedly bohemian vibe, originally developed in the early 1900’s as an artists’ colony and remaining a cherished destination for artists and creatives today. The city is a mere one square mile with a charming village-like center featuring galleries and shops, and cozy homes such as the fairytale cottages designed by architect Hugh Comstock and the only oceanside home ever designed by architect Frank Lloyd Wright. There are no street lights or numeric addresses, addresses are simply navigational points such as the Compass office at 6th Avenue 2 Southwest of San Carlos. “Carmel-By-The-Sea property lots are small and the typical home size is about 1600 square feet,” explains Michelle. “Homes in the prime ‘Golden Rectangle’ section with no ocean views start at about $4 million or $2500 per square foot, and those with ocean views increase in price accordingly. Luxury here is not about size. It is about location.”

Compass agent Jonathan Spencer grew up visiting his grandparents in Carmel, driving his lifelong passion for the landscape, lifestyle and inevitable decision to build a life on the Monterey Peninsula with his young family. Jonathan sheds light as to why luxury buyers here are willing to pay such high prices for such small properties. “These buyers prioritize community and accessibility. The mini-metropolis is completely unassuming, walk-to-all and culturally rich, with superb restaurants, stunning beaches and coastline, even designated spots for dogs to be off-leash. With its laid-back yet upscale vibe, it is no wonder the Bay area high net worth individuals (in tech and venture capital) desire a second or third home here, as well as those from Southern California, Texas, even New York and Chicago. It’s utterly idyllic.”

0 Mission 8 SE of 8th Avenue, Carmel, CA 93923

For those in search of a home with access to the amenities of Carmel-By-The-Sea but prefer more space and privacy, Jonathan recommends traveling a few miles south to the Carmel Highlands. This spot is his personal favorite place on the Monterey Peninsula. “For me, the Highlands create the perfect intersection for relaxation and recharging with all the conveniences. While you do trade off Carmel-By-The-Sea’s walkability, it’s still an easy drive to its restaurants and art galleries as well as the golf at Pebble Beach. In addition, your home buying dollar goes farther here. A $40 million Pebble Beach property may be $15 to $30 million for a comparable one in the Highlands.” Meanwhile, the secret of the Carmel Highlands’ unique desirability most definitely seems to be out: Jonathan’s record-breaking $26 million sale was recently eclipsed by the $40 million purchase of an historic home in the oceanside cliffs by none other than megastar Brad Pitt. (2)

“This is not simply a place, it’s a feeling. It’s a state of mind.”

With its arresting scenic beauty, Big Sur is a vast, largely undeveloped and protected region unlike any other, with dramatic rocky mountains rising precipitously off the edge of the crashing waves of the Pacific Ocean. When asked to describe the dreamlike, otherworldly landscape in his own words, Jonathan grows sentimental, “God created the Earth in six days and spent five of those days on Big Sur.” While the interior territory is largely uninhabited, the coastline is peppered with estates and ranches on massive properties, offering astonishing views and absolute privacy and quietude. Mark explains, “There is no Big Sur town center, it’s unspoiled and rugged with not much more than a post office and a deli. Big Sur is a place for cleansing and rebirth, and being there enriches the soul and the spirit. This is not simply a place, it’s a feeling. It’s a state of mind.”

Jonathan delves into the reasons luxury buyers are drawn to this rustic and spiritual yet isolated lifestyle. “Big Sur does not attract golfers, the drive from Big Sur to Pebble Beach is long. Big Sur is for those in search of the ultimate privacy play. It’s a challenge to even find someone’s home address here. Titans of tech and venture capital can disconnect in Big Sur and be completely off the grid, an essential component to their well-being. ” Well-known residents of Big Sur have included Ted Turner, Henry Miller, Jack Kerouac, Hunter S. Thompson, and Red Hot Chili Peppers' bassist Flea.

Highway 1, also known as the Pacific Coast Highway, runs along the coast of Big Sur and is widely considered among the most transcendent and magnificent sections of roadway in the entire county. In addition to its scenic panoramas and privacy, Big Sur offers hiking and outdoor activities, as well as a selection of luxury lodges and glamping resorts for those exploring the notion of living a life of peace, natural beauty and solitude.