Up, Down, and All Around Montecito’s Pepper Hill

This is the fifth in a series of fortnightly monthly occasional walks, on streets chosen more or less at random. Because when you slow down, you see so much more.

Located on the Montecito side of Eucalyptus Hill, the private community of Pepper Hill comprises two streets, Woodley Road and Glenview Road, which form a circle accessed via Alston Road or Sycamore Canyon Road.

The stone gateposts at each entrance hint that Pepper Hill was once a big estate. Indeed, zinc magnate David Benton Jones built a house there in 1916-1917. From the Pacific Coast Architecture Database:

A wealthy man with a nationwide zinc business, Jones maintained four residences, a town house in Chicago, a Colonial Revival summer house, Pembroke Hall (1895), in Lake Forest, IL, designed by Chcago architect Henry Ives Cobb (1859-1931), a house in FL, and Pepper Hill in Santa Barbara. The house was named “Pepper Hill” because pepper trees were grown in the surrounding landscape, scenting the air with the plant’s aroma. […]

Following [his daughter] Gwethalyn’s death, the family sold Pepper Hill to a real estate investor, Robert L. Scott, who chose to remove the Adler residence and sub-divide the land. […] In 1960 the estate was sold to Robert L. Scott and his wife for $450,000. During the early 1960’s Mr. Scott formed Pepper Hill Inc. and began offering lots that were approximately 1-acre in size, for between $18,000 and $32,000 apiece.

I started from Woodley and Sycamore Canyon. Immediately, you can see one reason the enclave makes for a delightful walk: Woodley and Glenview are always curving, and you’re often going uphill or downhill. A second reason: lovely vegetation.

There’s a mix of architectural styles, but because Pepper Hill was developed relatively late, it doesn’t have the occasional very old house mixed in. Below are two appealing entries, one modern and one traditional. The second motor court has a heck of a mountain view.

I’m always charmed by a mailbox hiding in a hedge. I’m less sure about the vase of fake red roses—not a grave marker, one hopes.

The 2008 house at 396 Woodley looms above Woodley’s and Glenview’s northern nexus. In the first photo, you can see a glimpse of the house above it, which was also designed by the Warner Group. The second photo, taken after I turned left onto Glenview, also shows the two houses. The owners of the higher house own the lot below, where they’re planting an orchard.

A dramatic entrance on Glenview.

And then the ocean.

Could this streetlight, nearly hidden in foliage, be from the initial Jones estate?

With a view like this, taking out the garbage doesn’t seem like such a chore.

What I haven’t mentioned yet is how much construction is going on in Pepper Hill. Every third house either has a Notice of Development posted out front or a crew already at work. I’ll be interested to see what happens with 1143 Glenview, where someone is starting from scratch.

But the uphill side of the street has even better views. Below: two nice gates.

And a bit of quirk.

This is the Glenview entrance to Pepper Hill, off Alston Road. While there are indeed speed bumps, construction workers regularly park on the side of the street, so you probably could just pretend to be one of them.

Heading uphill along Glenview.

Nice fence!

You can’t miss 351 Woodley, the fabulous underground lair being built by Bruce Heavin and Lynda Weinman. (More on the project, including renderings, can be found here.) I hope they’re documenting the construction, because the concrete is beautiful.

Across the street at 346 Woodley is a sharp, sexy contrast. It doesn’t seem to have ever changed hands.

Scenes from the Woodley spur that pokes into the west side of the Pepper Hill circle: old-school street-address signage; 358 Woodley’s glamorous driveway; an almost institutional motor court; a license plate that’s begging to get pulled over; and the harbor view on the way back.

Heading into the final turn of the circle…. As much as I love an ocean view, I often think the mountains are just more interesting. And it was only at the end of the walk that I realized another reason Pepper Hill makes for such a pleasant stroll. The lots are all irregularly shaped, and many of the houses are above or below street level, so that even though the original estate was subdivided, it was spared the drab suburban feel of houses sitting right next to each other like canned goods on a supermarket shelf.

Want to suggest a street? Email [email protected].

E. Canon Perdido, one of downtown’s best strolling streets
Montecito’s Prestigious Picacho Lane
Whitney Avenue in Summerland
School House Road and Camphor Place