Southshore Hills

Southshore Hills was built in two parts. The first, in 1970, is Highgate Road and the courts and terraces off it: Kelmscott, Brooksfall, Windbrook and Bayside courts, Bowcliff Terrace, and Woodburn Avenue, Elmsbury Road and Fallview Road. These are mostly two-story homes on lots of about 9,500 to 19,000 square feet. The second, recorded in 1974, climbs higher along Hillsbury Road, Channelford Road, Glastonbury Road and Folkestone Terrace, with Flinton, Kinross and Oakstaff courts. These are mostly single-story homes on larger, steeper lots.

Southshore Hills Park, a small Conejo Recreation and Park District park with a playground, sits at Glastonbury and Channelford roads in the middle of the hill. Windward Shores and the lake are just across Triunfo Canyon Road to the east.

Fifteen original plan sheets survive: four named plans from 1970 (the Aventine, Birchmont, Cherrywood and Treemont, with variants), and a numbered series, Plans 1 through 8, from the later section. The 1970 plans have vaulted, beamed living rooms, brick fireplaces, formal dining rooms and family rooms opening to the back patio. The later plans are mostly single-story.

The most common sizes in recent sales are 2,808 and 2,823 square feet—two-story plans with four or five bedrooms and three baths—and about 2,130 square feet, a single-story plan with three or four bedrooms and two baths.

Drawings on file for the tract. Other plans, elevations and options may have been offered.

The upper streets look over the western arm of the lake and the valley, and some toward the Santa Monica Mountains. How much you see depends on the exact lot, the trees and the roof below. Sloped lots and flag lots mean retaining walls, drains, long driveways and sometimes shared driveway easements, so read the title report and walk the whole lot.

Every home belongs to the Southshore Hills property owners association. It has no pool, clubhouse or gate, so dues are low: about $600 to $725 a year on most recent sales. A few listings on the 1974 streets show lower amounts, so confirm the current dues in escrow. The association maintains common areas and reviews exterior changes.

Southshore Hills is in the Conejo Valley Unified School District: Westlake Elementary, Colina Middle School and Westlake High School. The Los Angeles County side of the lake is in Las Virgenes Unified, so confirm the assignment for a specific address with the district.

Traffic leaves the hill by Triunfo Canyon Road to Westlake Boulevard, which runs north to the 101 in a few minutes, past the shopping centers at Agoura Road and Townsgate Road.

These are early-1970s homes: galvanized supply lines in homes that have not been repiped, Zinsco or Federal Pacific panels, single-pane sliders and long sewer laterals on the flag lots. On the hillside, add slopes, retaining walls and drainage. The upper streets back onto open hillside, so check brush-clearance requirements and get an insurance quote early in escrow.

17 homes sold between September 2024 and September 2026, from $1,500,000 to $2,400,000, with a median of $1,725,000. The 2,808- and 2,823-square-foot two-story homes sold between $1,625,000 and $1,935,000. Single-story homes sold between $1,500,000 and $2,400,000, with the lot and the view making most of the difference.

The top sale was $2,400,000 in April 2025 for a remodeled single-story on Channelford Road, which had sold for $2,250,000 seven months earlier. Highgate Estates, a new-construction enclave at the top of Highgate Road with its own association, is not part of the tract.

Foxmoor Hills, across Westlake Boulevard, is the closest match: a 1969–71 hillside tract with similar plans, lots and schools, low dues and a median of $1,795,000 over the same period. Southshore Hills has more single-story homes and more lake views. Three Springs, to the south, offers larger late-1980s homes. Windward Shores, across Triunfo Canyon Road, puts a single-story home on the water at a higher price.