Three streets: Covewood Street along the slope and the two courts, Bellagio and Benedict, off it. The lots are zero-lot-line by a secondary source’s description, about 5,300 square feet at the median, and the outer lots back to the open space of the hills; the secondary source notes that private pools are rare on lots this size. The tract is secluded, with no through traffic, and the Westlake Village shops on Lindero Canyon Road are a few minutes below.

The sale record shows three plans, the same three that appear in Hillcrest Pointe: a 2,041-square-foot three- or four-bedroom, a 2,095-square-foot three-bedroom and a 2,382-square-foot four-bedroom, all two story on lots of about 3,800 to 6,800 square feet. The top is $1,249,900 on Bellagio Court in June 2024 and $1,245,000 on Bellagio Court in April 2026, both for the 2,041, and $1,240,000 on Benedict Court in October 2025 for the 2,382. The bottom is $820,000 on Covewood Street in November 2020 for the 2,095, and $900,000 on Benedict Court in March 2020 and October 2023. Four of the six sales are four-bedrooms and two are three-bedrooms.

No plan sheet for Hillcrest Estates 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 2,041 to 2,382 square feet, median 2,095, with four bedrooms in four of the six, three in two, and every recorded sale is two story.

The first reason is the seclusion, a hillside tract with no through traffic and open space behind the outer lots. The second is the view, from the lots that have one. The third is the price of a 2,000- to 2,400-square-foot house in the district near $1,240,000, with a fee small enough to ignore. The fourth is the Westlake Village side of the community, closest to the Lindero Canyon shops and the interchange.

Listings report the fee at $100–$110 a month, most recently $110 on 2025 and 2026 sales. The recorded sales report association fees from $100 to $110 a month, and listings describe a greenbelt in the amenities. One secondary source gives about $104 a month; another says there is no association, which the sale record contradicts.

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.

Oak Park is its own school district, Oak Park Unified, a small independent K–12 district formed in 1977 and one of the main reasons buyers choose the community. The district publishes an elementary boundary street list, and every street in this tract’s sale record — Bellagio Court, Benedict Court and Covewood Street — is assigned to Oak Hills Elementary. The district has one middle school, Medea Creek, and one high school, Oak Park High, so there is no boundary question above fifth grade. The street list this guide relies on is dated 2017; confirm the current assignment with the district office before relying on it.

The open space of the hills is behind the outer courts, the Westlake Village shops on Lindero Canyon Road are a few minutes down the hill, and Oak Hills Elementary, Indian Springs Park and the Oak Park Plaza are a short drive. Oak Park runs on its parks, its trails and its one shopping center: the Oak Park Plaza at Kanan Road and Lindero Canyon Road for the supermarket, the pharmacy and the everyday errands, Oak Canyon Community Park with the duck pond and the splash pad, Deerhill Park and Medea Creek Park for youth sports, the Medea Creek trail down the middle of the community, and the Palo Comado and Cheeseboro trailheads into the Santa Monica Mountains National Recreation Area. Everything else is in Agoura Hills or Westlake Village, five to ten minutes away, and the Ventura Freeway is reached down Kanan Road to the Kanan interchange or down Lindero Canyon Road to the Lindero interchange.

Hillcrest Estates is on the Lindero Canyon Road side of Oak Park, and the Lindero Canyon interchange in Westlake Village is about seven minutes down the hill; Kanan Road to the Kanan interchange is the alternative. Errands are in Westlake Village or at the Oak Park Plaza; the Westside is forty minutes on a good day and ninety on a bad one.

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 April 2026, two homes in the tract sold through the MLS, at $1,240,000 and $1,245,000. Over the longer record since March 2020, six sales ran from $820,000 to $1,249,900 with a median of $1,240,000. The top of the record is $1,249,900 on Bellagio Court in June 2024 for a 2,041-square-foot four-bedroom; $1,245,000 on Bellagio Court in April 2026 for a 2,041-square-foot four-bedroom; $1,240,000 on Benedict Court in October 2025 for a 2,382-square-foot four-bedroom. The bottom is $820,000 on Covewood Street in November 2020; $900,000 on Benedict Court in March 2020; $900,000 on Benedict Court in October 2023.

Six sales in six years from $820,000 to $1,249,900 is one band that has moved: $820,000 to $900,000 in 2020 and $1,240,000 to $1,249,900 since 2024, with three sales inside $10,000 of one another. The record is short because the tract is small and its owners stay. 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 Hillcrest Estates; 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.

These homes date from 1989, and the inspection carries the 1980s list: original furnaces and condensers at end of life, tile-roof underlayment nearing the end of its span, failed dual-pane seals, and for 1985 to 1989 the possibility of polybutylene supply lines, which a plumber should be asked about by name. 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 1980s 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 Hillcrest Pointe on the hilltop above, 1990 to 1993 with the same three plans on similar lots and a similar fee, which trades at a median of $1,115,000 on a ten-sale record with a top of $1,480,000. Bent Tree, 1987 to 1988 below on the flat, is larger houses on larger lots without a fee at a median of $1,400,000. Monaco, 1989 to 1992, is 1,694- to 2,387-square-foot houses without a fee at $1,175,000. The two Hillcrest tracts are the same house; the difference is the year, the hilltop and the street.

Start with the lot: open space behind, or a neighbor, and the slope and drainage that come with a hillside. Then the house, briefed for 1989, with a plumber asked by name about polybutylene supply lines. Then the yard, since the lots are small and a pool will not fit on most of them. Then the association, from the disclosure package. A buyer who needs a single story should look at Bent Tree or Rolling Hills Estates.

Families first, for the courts, the seclusion and Oak Hills. Buyers moving over from Westlake Village second, for the district on the Westlake side. Empty nesters third, for a house with a view and little to maintain.

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 1980s. 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 — $1,249,900 — 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.

Oak Park is an unincorporated community of Ventura County, and it was built out as a sequence of tracts from the late 1960s to the early 2000s under the county’s planning. Metropolitan Development Corporation bought the ranch land in the 1960s and the first houses went up on the valley floor in the late 1960s; the Municipal Advisory Council formed in 1975 and persuaded the county to cut the planned build-out from 26,000 residents to about 15,000, and the community seceded from Simi Valley Unified to form its own school district in 1977. The tracts of the 1980s and 1990s filled the slopes on either side of Kanan Road, and the last of them, above Deerhill Road, were finished in 2002.

Hillcrest Estates was built in 1989 on the slope at the west edge of the community, the first of the two Hillcrest tracts; Hillcrest Pointe followed on the hilltop above it from 1990 to 1993 with the same plans. The county records show about 82 parcels inside the outline, which matches a secondary source’s count of about 80. The MLS files the sales as Hillcrest Estates; the developer is not named in any source Gary Jacobs has been able to verify.