Cinematic $17 Million Montecito Estate on Historic Pepper Hill Hits the Market for the First Time in 20 Years

Perched high above Montecito in one of the area's most storied neighborhoods, a Mediterranean estate on the market for the first time in 20 years offers buyers a chance to own a piece of California history.

Priced at $17 million, the expansive residence at 358 Woodley Road blends Pacific views and architectural grandeur with historical roots tied to the original Pepper Hill estate.

The 8,000-square-foot home, built in 2003, sits on land that once belonged to a much larger property that dates back to the early-20th century. The site's origins trace back to industrialist David Benton Jones, who developed Pepper Hill around 1916, according to listing agent Tracy Tutor from Compass.

"Jones assembled the entire Pepper Hill hillside in the early 1900s as a private estate, naming it 'Pepper Hill' after the pepper trees that scented the landscape," explains Tutor. "What’s incredible is that what are now 48 individual properties, including 358 Woodley, were once all part of one single estate."

Remnants of the site's history remain embedded in the property today, including original 110-year-old balustrades and walls that still grace portions of the grounds.

"There's a real sense of legacy here," says Tutor. "You're not just buying a home, you're owning a piece of Montecito's history."

The seven-bedroom Mediterranean-style home was designed to maximize its incredible setting, offering panoramic views of the Pacific Ocean, Channel Islands, and Santa Ynez Mountains from nearly every vantage point.

"What really stands out is the home's positioning and flow," notes Tutor. "It was designed to capture panoramic views from nearly every room while creating a seamless indoor-outdoor experience that feels both elevated and effortless.”

The grounds are equally memorable. A tranquil pond, working water wheel, and limestone patios embedded with marine fossils create a landscape that feels deeply connected to the land.

The resort-style pool anchors the outdoor entertaining spaces, while lush plantings enhance privacy across the 1-acre lot.

Location is another defining feature, as Pepper Hill remains one of Montecito's most coveted enclaves, prized for both its privacy and proximity to the village centers.

Residents are just minutes from the Upper Village’s restaurants and boutiques, Coast Village Road's renowned dining scene, and iconic destinations such as Butterfly Beach and San Ysidro Ranch. An abundance of hiking trails and coastal recreation opportunities are also just a short drive away.

"There are very few homes where you can sit on your balcony and take in unobstructed views of the Channel Islands by day, and then watch rocket launches from Vandenberg light up the sky at night," says Tutor.

"It's that combination of natural beauty, history, and something almost cinematic that makes this property feel truly one of a kind."