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.

Trentwood was built from 1994 to 2000 on the shore of the lake, inside the guard gates, as the attached community of the Sherwood development: townhomes on the water with docks, a greenbelt, guest parking and the lake carried as the amenities. The developer is not confirmed in any source Gary Jacobs has been able to verify. What the record shows is a community of about 36 townhomes of 1,964 to 3,758 square feet, two to four bedrooms on two or three levels, with dues that listings report from $1,628 to $4,200 a quarter.

The record shows three plans. A 1,964-square-foot two-bedroom on three levels, which holds the bottom of the record at $1,600,000 on Swanfield Court in April 2024. A 2,835- to 3,281-square-foot three- or four-bedroom on three levels, the median plan, which sold from $1,825,000 on Swanfield Court in January 2024 to $3,135,000 on Heatherbank Court in June 2026. And a 3,758-square-foot four-bedroom on two levels, the largest, which holds the top at $3,335,000 on Heatherbank Court in September 2024. None of the nine is single level.

No plan sheet for Trentwood is in the Conejo Simi Moorpark Association of Realtors archive that this guide series draws on, so there is no drawing to reproduce. The sale record shows homes of 1,964 to 3,758 square feet, median 3,281, with four bedrooms in four of the nine, three in three, two in two, and every recorded sale is two story.

Three courts inside the gates: Swanfield Court, which carries five of the nine sales, Heatherbank Court with three and Crombie Court with one. The homes on the water with a dock trade at the top of the record and the homes set back from it at the bottom; Heatherbank Court holds the top three sales.

The first reason is the water: a dock at the door, in an attached home, which nothing else at the lake or in the Conejo Valley offers. The second is the guard gate shared with the club. The third is the plan: 3,281 square feet at the median with three or four bedrooms is a house’s worth of space. The fourth is the lock-and-leave, for an owner who wants the lake without the grounds.

Listings report the fee at $1,628–$4,200 a quarter and $1,466 a month; 2026 sales reported up to $1,466 a month, and the most recent, in June 2026, $2,341 a quarter (about $780 a month). The fee carries the guard gates and their staffing, the buildings’ exteriors and roofs, the docks, the greenbelt and the common landscaping, guest parking and an architectural review; the range in listings reflects different sections and different years, and which of the insurance, water and trash are included is what the disclosure package answers. The Sherwood Country Club and the lake club are separate; the dues do not include them.

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 docks, and the Sherwood Lake Club and the country club are a few minutes away for their 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 gate.

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 June 2026, 7 homes in the tract sold through the MLS, at prices from $2,100,000 to $3,850,000 and a median of $3,100,000. Over a longer record, nine sales from April 2021 through June 2026 ran from $1,600,000 to $3,335,000 with a median of $2,625,000. The top of the record is $3,335,000 on Heatherbank Court in September 2024 for a 3,758-square-foot four-bedroom; $3,135,000 on Heatherbank Court in June 2026 for a 3,281-square-foot four-bedroom. The bottom is $1,825,000 on Swanfield Court in January 2024; $1,600,000 on Swanfield Court in April 2024.

Nine sales in five years is a range rather than a trend. What the record supports is a floor near $1,600,000 to $1,825,000 for the smaller plans set back from the water, and a band from $2,600,000 to $3,335,000 for the larger plans on the water with a dock, with the top set twice on Heatherbank Court in 2024 and 2026. Gary Jacobs keeps the full sale-by-sale history and can say where a given home sits in it.

No lease is recorded in the MLS sources this guide draws on, so it does not quote a rent. Lake leasing here is occasional and private, and the association’s leasing rules apply.

These homes date from 1994 to 2000, and the inspection carries the 1990s list: original systems at end of life, tile-roof underlayment approaching the end of its span, failed dual-pane seals, and for 1990 to 1994 the possibility of polybutylene supply lines. In attached communities add the association questions: who owns the roof, the exterior walls and the plumbing inside them, when the buildings were last repiped or reroofed, and whether the reserves are funded for the next round. Ask the association for the roof and plumbing history in writing.

In attached communities the remodel that pays is inside the walls: the kitchen opened to the living room, the baths, the floors, the windows where the association allows, and a laundry brought into the unit. What does not pay is anything the association will not approve or that the next buyer cannot see from the listing photos. Check the rules before the plans.

The comparison is the rest of the lake. The Lake Sherwood lakeside houses, outside the club, trade at a median of $4,150,000 with the water as the premium. Sherwood Country Club, behind the same guard gates, trades at a median of $5,100,000 across houses from 3,025 to 9,304 square feet. Thistleberry, the older hillside above the west end of the lake, trades at a median of $2,425,000 with no gate. Trentwood is the only attached community on the water, and it trades between Thistleberry and the shore houses at the median, with the dock the reason.

Start with the position, because it is most of the price: on the water with a dock, or set back. Then the association package, because the dues are the largest variable at the lake: the fee for the unit and the section, what it covers, the reserve study for the docks and the 1990s roofs, the insurance certificate and the minutes. Then the plan and the levels, since most of the homes are on three. Then the unit, with the inspector briefed on 1994 to 2000 and asked about polybutylene supply lines by name for 1994.

Lake buyers first, who want the dock without the grounds. Downsizers second, from the club and the shore houses, though the levels rule out some of them. Second-home buyers third, for the lake within an hour of the Westside.

For a buyer, read the plan off the square footage and the level, take the association package from the disclosures before the inspection, and brief the inspector for the 1990s. Pull the permit history of any addition, pool or converted garage from the county. Confirm the school assignment for the exact address.

For a seller, the comparable is the same plan, and the top of the record — $3,335,000 — is the renovated house on the better lot. Price to the record for the plan, say the association fee and the school assignment in the first lines of the listing, and let the condition argue for the top of the band.