Westlake Island

La Venta Drive crosses the bridge past the guard house and splits into the island’s loop. The streets carry a sailing theme. Whitesail, Mariner, Freshwind and Fairbreeze Circles are on the Los Angeles County half; Bluesail, Redsail, Eastwind, Southwind and Westwind Circles are on the Ventura County half; and Oakshore Drive and La Venta Drive ring the island. Nearly every street is a short loop or cul-de-sac, so there is no through traffic.

The county line crosses the island rather than following a street. House numbers are the quickest tell: the 3900s and 4000s on the circles and the 32100s on Oakshore are Los Angeles County; the 1200s to 1500s on the circles and the 2400s on Oakshore are Ventura County. The Los Angeles side went up first, from about 1967; the Ventura side mostly between 1975 and 1979.

Mainsail, Bowsprit, Charthouse, Capstan, Brigantine and Weatherly Circles have the same nautical names but are on the mainland in Southshore, not on the island. Their sales are not island comparables.

Because every lot is on the water, the difference between lots is the kind of water. Homes on the outer edge face the main lake, with long views across to the shore and toward The Landing, and they sell for the most. Lots on the interior finger channels look across a narrow waterway at the neighbors’ docks and sell for less. Width matters more than area, since it sets how much dock and lake a house gets.

Ten original plans survive in the Conejo Simi Moorpark Association of Realtors archive, all with nautical or island names: Bahama, Buccaneer, Caribbean, Columbia, Constellation, Dover, Empress, Intrepid, Islander and Martinique. Each was drawn with the living room, family room and primary bedroom on the water side and the garage and entry on the street side. Most were single-story or two-story plans of 2,000 to 3,000 square feet.

Many island homes are no longer the original plan. Owners have added second stories, extended toward the water or rebuilt from scratch, which is why some homes here were finished in 2008, 2015 and 2021. Assume any island listing over about 3,500 square feet has been expanded or rebuilt, and check the permit history.

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

Westlake Lake and its dam are private, owned and run by the Westlake Lake Management Association (WLMA), and buying on the island makes you a member. Its rules shape life on the water. Boats may be no longer than 18 feet or wider than 8 feet 6 inches, and every powerboat must be electric. The speed limit is 5 mph on the open lake and 3 mph in the channels. Jet skis, inflatables, paddleboards and multi-hull sailboats are not allowed, and neither is swimming. Fishing takes an annual WLMA badge.

A private dock is a WLMA permit, not a deeded right. It transfers to a buyer automatically only if the seller is in good standing with the association, so the good-standing letter, the dock permit file and the boat registrations belong in due diligence. Dock repairs and changes need WLMA’s written approval, and WLMA alone repairs the seawall.

Every owner belongs to two associations: the Westlake Island Property Owners Association, which pays for the guard gate, the bridge, the private streets and the common areas, and WLMA, which owns and maintains the lake and dam. The 2026 sales showed $950 a quarter for the two combined, up from about $850. Listings have reported the split between them in different ways, so the escrow documents are the only reliable figure. WLMA charges separately for annual lake-use badges and for dock and boat registration.

The county line is also a school-district line. Homes on the Los Angeles County streets, in the City of Westlake Village, are in Las Virgenes Unified: White Oak Elementary, Lindero Canyon Middle School and Agoura High School. Homes on the Ventura County streets, in the City of Thousand Oaks, are in Conejo Valley Unified: Westlake Elementary, Colina Middle School and Westlake High School. Neighbors a few hundred feet apart can attend different high schools, so confirm the assignment for the exact parcel.

Every trip starts across the bridge to Triunfo Canyon Road. Westlake Boulevard reaches the 101 about a mile north, and Lindero Canyon Road has its own interchange to the east; either is about five minutes from the gate outside rush hour. The Landing’s restaurants are a few minutes away by car and about the same by electric boat, and boats may tie up at The Landing’s guest docks for up to two hours.

The original houses carry the systems of their era: galvanized pipe in some of the earliest homes, Zinsco or Federal Pacific panels, aluminum branch wiring in some late-1960s homes and single-pane aluminum sliders along the water side. The island is built on fill, so look for slab moisture on the water side, settlement cracks in the patios and drainage that pools behind the seawall.

A home inspection does not cover the dock. Have a marine or dock contractor check it, and ask WLMA what its records show about the seawall. Patios and decks built toward the water are the most common unpermitted additions; permit history comes from the City of Westlake Village on the Los Angeles side and the City of Thousand Oaks on the Ventura side.

Country Club Estates, Lake Sherwood, Sherwood Country Club, Sycamore Canyon, Thistleberry, Trentwood.

See all 28 Westlake Village gated communities on one map →

Six homes sold between January 2025 and September 2026, from $2,800,000 to $3,300,000, with a median of about $3,016,000. Per square foot they ranged from about $850 to $1,450, which says more about frontage and position than about the houses. Since 2020, island sales have run from $1,799,000 for a smaller original home to $5,850,000 for a large rebuilt house on the main lake.

Turnover is low, a few sales a year across about 330 homes, so a buyer who wants a particular kind of frontage may wait a year or more. Island escrows also tend to run longer, usually over association and dock paperwork.

Westlake Island sells for roughly one and a half to two times the price per square foot of the tracts around it, on the smallest lots and with the highest dues. First Neighborhood, on the east shore, has similar-era homes, a pool and greenbelts, and the same Las Virgenes schools as the Los Angeles side of the island, at roughly half the price per foot. Three Springs, in the hills south of the lake, offers a house a thousand square feet larger on a lot two to three times the size. Foxmoor and Village Homes share the Conejo Valley schools of the Ventura side. None of them has a gate or the water.