Southshore was one of the first tracts on the water. Westlake Lake was filled in the late 1960s as the centrepiece of the master plan, and the south shore was subdivided as tract 719, marketed as The Shores, and built from 1970 to 1973 on the circles off Southshore Drive. The lots are small, about 5,000 to 7,500 square feet on most of the circles, because the water was the point; the houses on the outside of the circles back onto the lake with docks, and the ones inside look across the street at them.

The developer is not confirmed in any source Gary Jacobs has been able to verify. What the archive holds is the three original plan sheets, one single story and two two-story, reproduced below, and what the record shows is a tract where the original houses trade in one band and the rebuilt ones in another: $1,500,000 to $3,050,000 for the 1970s plans, and $5,995,000 to $8,750,000 for the three new houses on the water — a 4,485-square-foot house built in 2022 on Mainsail Circle and two 5,800-square-foot houses built in 2024 on Brigantine Circle.

Three plans are on file: Plan 1 on one level, and Plans 2 and 3 on two. The sale record matches the originals at 1,568 to 2,653 square feet, with the 2,653-square-foot four-bedroom the most common; two of the twelve sales are single story, and the 1,568-square-foot two-bedroom that sold for $1,500,000 in May 2024 is the smallest. The rebuilds — 4,485 square feet on Mainsail Circle in 2022, and 5,788 and 5,816 square feet on Brigantine Circle in 2024, which sold for $8,000,000 and $8,750,000 in 2025 — are what the water lots become when the house is replaced.

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

Southshore Drive runs along the lake and the circles come off it: Mainsail, which carries five of the twelve sales, Capstan with three, Brigantine with two, and Leeward and Bowsprit. Each circle has an outside, on the water, and an inside, across the street. The lots run from about 4,900 to 11,300 square feet, median about 6,800, with the largest on Brigantine Circle; the difference between a lake lot and an inside lot is the whole difference in the record.

A lake lot comes with a dock, the right to keep a boat on the water — electric or non-motorised, under the lake association’s rules — and a second fee: the Westlake Lake Management Association assesses lakefront owners for the lake’s upkeep separately from any tract association. Listings report fees of $91 to $136 a month and $935 to $2,091 a year, with $1,100 a year on most 2024 and 2025 sales and $91 a month on the latest, in March 2026; which of those is the lake assessment and which the tract association is a question for the disclosure package. The lake is private; there is no public access.

The first reason is the water: a dock on a private lake five minutes from the freeway, on a lot that costs a fraction of the Island. The second is the plans, on file, so a buyer knows the house before the showing. The third is the range: an original inside-lot house at $1,500,000 and a rebuilt water lot at $8,750,000 in the same tract. The fourth is the record of rebuilds, three since 2022, which says the water lots support a new house at the top of the Westlake Village market.

Listings report the fee at $935–$2,091 a year and $91–$136 a month, with $1,100 a year on most 2024–2025 sales and $91 a month on the latest, in March 2026. The tract association carries the greenbelt; lakefront owners also pay the lake management assessment, which carries the water, the shoreline and the docks.

What the association covers and what the CC&Rs restrict is not confirmed in any source Gary Jacobs has been able to verify. Take the budget, the reserve study, the insurance certificate and the CC&Rs from the seller’s disclosure package, read the minutes for any special assessment or litigation, and confirm the current fee with the manager before removing a contingency.

Los Angeles County side of Westlake Village, so Las Virgenes Unified: White Oak Elementary, Lindero Canyon Middle School and Agoura High School are the assignments listings give for this side of the city. Confirm the exact address with the district locator; the county line is also the district line, and it runs through the middle of the community.

Westlake Village runs on the lake and the promenade: the Landing and the Westlake Village Inn on the water, the shops and restaurants along Agoura Road and Westlake Boulevard, the YMCA, the community park, and Triunfo Creek and the Santa Monica Mountains trails within a few minutes. The Ventura Freeway crosses the middle of the community, and most tracts are five minutes from an on-ramp; the drive to the Westside is the same forty minutes to ninety it is from anywhere in the Conejo Valley.

The Ventura Freeway is the spine of the Conejo Valley, and this tract is a few minutes from an on-ramp. Errands are along Agoura Road, Westlake Boulevard and Lindero Canyon Road; the Westside is forty minutes on a good day and ninety on a bad one, and a buyer who commutes should time it at 7:30 in the morning before deciding.

The figures in this section were current when this guide was last reviewed. The sale record in the facts above and the listings below are drawn live from the MLS each time the page loads.

In the two years through September 2026, six homes in the tract sold through the MLS, at prices from $2,259,000 to $8,750,000 and a median of $3,350,000. Going back to October 2020, twelve sales are on record, from $1,500,000 to $8,750,000 with a median of $2,757,500. The top of the record is $8,750,000 on Brigantine Circle in April 2025 for a 5,816-square-foot five-bedroom; $8,000,000 on Brigantine Circle in January 2025 for a 5,788-square-foot five-bedroom. The bottom is $1,625,000 on Mainsail Circle in October 2020; $1,500,000 on Mainsail Circle in May 2024. Single-story homes account for two of the twelve sales, at a median of $1,982,500.

The record is two markets on the same streets. The original 1970s plans have moved with the rest of the Conejo Valley, sharp appreciation from 2020 into 2022 and a band since, with the premium going to the lot and the renovation. The water lots are a different calculation: three rebuilds since 2022 have sold at $5,995,000 to $8,750,000, and a buyer of an original house on the water is buying the lot and the dock as much as the house. Gary Jacobs keeps the full sale-by-sale history and can say where a given house sits in it.

No lease is recorded in the MLS sources this guide draws on, so it does not quote a rent for Southshore; a current figure should come from the leasing agents who work these streets. Each association’s leasing rules — minimum terms, caps, pet rules — should be read before buying as an investment.

The original houses date from 1970 to 1973, and their inspection carries the 1970s list: galvanised or early copper supply lines, original panels, single-pane windows where not replaced, original furnaces and water heaters, wood-shake roofs long since replaced but sometimes with the sheathing still original, and cast-iron or clay sewer laterals. On the water add the seawall, the dock and the drainage toward the lake, which a general inspector will flag but a marine or structural contractor should answer; pools of this age often have original equipment and plaster. The 2022 and 2024 rebuilds carry a new-house list instead: the builder’s warranty, the permit final and the drainage. None of this is unusual; all of it is negotiable if it is found before the contingency comes off rather than after.

In a tract of this era the remodels that return their cost are the ones that bring a 1970s plan to the way people live now: the kitchen opened to the family room, the primary bath and closet, the floors and the glass, and, on a water lot, the rear of the house opened to the lake. What does not return its cost on an inside lot is the addition that pushes the house past what the street will support; on a water lot the record shows a full rebuild can, three times since 2022, which is a different calculation entirely.

The comparison is the other water tracts. Westlake Island, 1970 to 2018 across the bridge, is the gated island of the same era at a median of $2,775,000. Lakeshore, 1967 to 1969 on the north side, is 1,961-square-foot houses at a median of $1,160,000, mostly off the water. Northshore, 1973 townhomes on the water, trades at a median of $1,055,000. Southshore Hills, above the tract, is 1970 to 1981 houses at a median of $1,625,000. Southshore sits between Lakeshore and the Island: the original plans trade with Southshore Hills, and the water lots trade with the Island and, when rebuilt, above it.

Start with the lot: water or inside, and if water, the dock, the seawall and the lake assessment. Then the plan, from the sheets. Then the house, with the inspector briefed for the early 1970s and, on the water, for the seawall and the dock. Then the lake rules: boat type, dock repairs and who pays for the shoreline.

Lake buyers first, choosing between Southshore and the Island. Rebuilders second, for an original house on a water lot. Families third, for a four-bedroom in the Las Virgenes district on an inside lot at the bottom of the record.

For a buyer, read the plan off the square footage and the level, take the association and lake packages from the disclosures before the inspection, and brief the inspector for the 1970s. Pull the permit history of any addition, dock or converted garage from the city and the lake association. Confirm the school assignment for the exact address.

For a seller, the comparable is the same plan on the same kind of lot, water or inside, and the top of the record — $8,750,000 — is a new house on the water. Price to the record for the lot, say the dock, the fees and the school assignment in the first lines of the listing, and let the condition argue for the top of the band.