The lake itself is a reservoir, formed by a dam across the Potrero valley early in the twentieth century, and the name came from Hollywood: the valley stood in for Sherwood Forest in the silent-era Robin Hood pictures, and the name stayed. The cabins and lake houses of the 1920s through the 1960s grew up along the shore and the roads above it, and the country club, the gates and the modern tracts came in the late 1980s and 1990s, when the surrounding ranch land was developed around a Jack Nicklaus course. Every community at the lake is unincorporated Ventura County with the Conejo Valley Unified schools, and most carry Westlake Village or Lake Sherwood mailing addresses.

The Upson Tract was subdivided in the 1920s along the north shore, when the lake was a weekend and summer place reached by a long drive from the city, and its cabins were the first houses at the lake. The developer is not confirmed in any source Gary Jacobs has been able to verify beyond the tract name in the county record maps. What the record shows is about 20 parcels on Lake Sherwood Drive, with the lake and its picnic areas carried as the amenities, no tract association and a lake association fee that listings do not consistently report.

No homes in the tract have sold through the MLS in the two years through September 2026. One sale is on record since 2020: a 777-square-foot two-bedroom cabin from 1932 on two levels, on a 15,900-square-foot lot on Lake Sherwood Drive, which sold for $909,000 in May 2024. At that size the sale is the lot and the lake rights rather than the house, and it is the best evidence in the record of what a north-shore parcel is worth apart from what stands on it.

No plan sheet for Upson is in the Conejo Simi Moorpark Association of Realtors archive that this guide series draws on, so there is no drawing to reproduce. The one recorded sale since 2020 was a 777-square-foot two-bedroom cabin on two levels.

One street, Lake Sherwood Drive, along the north shore. The parcels run down to the water, and the ones with usable frontage and a dock are the ones that matter.

The first reason is the water: north-shore frontage on a private lake, at the lowest entry the lake offers. The second is the history, the original cabins of the 1920s and 1930s. The third is the lot: a parcel to rebuild on, with the value of the lake rights already in the price. The fourth is the absence of a gate and a tract fee.

The lake association fee carries the private lake, its docks, picnic areas and security. There is no tract association and no gate; the constraint on an owner is the county permit process rather than an architectural committee, and the title report says what attaches to the specific parcel.

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.

Lake Sherwood is unincorporated Ventura County in the Conejo Valley Unified district: Westlake Elementary or Westlake Hills Elementary, Colina Middle School and Westlake High School are the assignments listings give. Confirm the exact address with the district locator; the drive to any school is east on Potrero Road.

The lake is at the door, with the Sherwood Lake Club on the water for members, and the country club a few minutes east for its own members. Lake Sherwood runs on the lake and the club: the private lake with its docks, the Sherwood Country Club and its Jack Nicklaus course for members, the Sherwood Lake Club on the water, and the Potrero Road drive east to Westlake Boulevard for everything else. The shops at Westlake Boulevard and Agoura Road are about ten minutes, the Ventura Freeway fifteen, and the drive to the Westside is the same forty minutes to ninety it is from anywhere in the Conejo Valley, plus the ten minutes in from the gate.

Potrero Road runs east to Westlake Boulevard in about ten minutes and to the Ventura Freeway in about fifteen. Errands are at Westlake Boulevard and Agoura Road; the Westside is forty minutes on a good day and ninety on a bad one, plus the drive in from the lake.

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.

One sale is on record, in May 2024: $909,000 on Lake Sherwood Drive in May 2024 for a 777-square-foot two-bedroom.

One sale in six years is a data point rather than a market. What it supports is a value near $900,000 for a north-shore parcel with an original cabin, which is the floor; a rebuilt house on the same parcel would trade with the Lake Sherwood lakeside streets, where the median since 2020 is $4,150,000. Gary Jacobs keeps the full history of the lake and can say where a given parcel sits in it.

No lease is recorded in the MLS sources this guide draws on, so it does not quote a rent.

These homes date from 1932, and the inspection carries the late-1960s list: original galvanised supply lines, original electrical panels of brands insurers now flag, single-pane aluminum windows where not replaced, original furnaces and ductwork, and roofs and sewer laterals at or past end of life. Slope lots add drainage and retaining-wall questions that a general inspector will flag but a geotechnical engineer should answer; pools of this age often have original equipment and plaster. 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 1930s 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 the right lot, the pool. What does not return its cost is the addition that pushes the house past what the street will support; the record shows the top sales are renovated versions of the original plans on the better lots, not the biggest houses.

The comparison is the rest of the lake outside the gates. The Lake Sherwood lakeside streets trade at a median of $4,150,000 for houses of 2,835 to 6,616 square feet. Thistleberry, the older hillside above the west end, trades at a median of $2,425,000 for houses from a 1963 cabin to a 2016 rebuild. Trentwood, the guard-gated townhomes on the shore, trades at a median of $2,625,000. Upson is where the lake began, and its parcels trade on the water and the lake rights rather than the cabins.

Start with the parcel, because it is the whole purchase: the title report for the lake rights, dock rights, access and every easement, the county for fire mapping, septic and slope, and an insurance quote early, because a 1930s cabin on a lake prices differently. Then the county’s view of a rebuild: setbacks, the lake, the slope and the road. Then the cabin, inspected for what it is, with the permit history of every change pulled from the county. Then patience: one sale in six years.

Builders first, for a north-shore parcel to rebuild on. Lake buyers second, who want a cabin on the water as a second home. Owners at the lake third, adding a parcel next door.

For a buyer, start with the title report for the lake rights, the access and every easement, and the county for what can be built on the parcel. Inspect the cabin for what it is, and pull the permit history from the county. Confirm the school assignment for the exact address.

For a seller, the comparable is the parcel and the frontage rather than the cabin, and the one sale on record — $909,000 for a 1932 cabin on 15,900 square feet — is the floor. Price to the water and the lot, say the lake rights and the frontage in the first lines of the listing, and let a buyer who wants to build see the parcel first.