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 Pointe was built from 1990 to 1993 on the hilltop above Hillcrest Estates, the second Hillcrest tract, with the same three plans as the first. The county records show about 101 parcels inside the outline, in line with a secondary source’s count of about 100. The MLS files the sales as Hillcrest Pointe; the developer is not named in any source Gary Jacobs has been able to verify.

The sale record shows three plans: a 2,041-square-foot three-bedroom, a 2,095-square-foot three-bedroom and a 2,382-square-foot four-bedroom, all two story on lots of about 3,400 to 7,200 square feet. The top is $1,480,000 on Churchwood Drive in December 2025 for the 2,382, $1,325,000 on Churchwood Drive in April 2025 for the same plan and $1,275,000 on Churchwood Drive in May 2025 for the 2,095. The bottom is $927,000 and $960,000 on Monteleone Avenue in September 2020 and $990,000 on Monteleone Avenue in April 2023. Seven of the ten sales are three-bedrooms and three are four-bedrooms. A secondary source describes open plans, high ceilings and, on some lots, room for a pool.

No plan sheet for Hillcrest Pointe 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 three bedrooms in seven of the ten, four in three, and every recorded sale is two story.

Churchwood Drive on the hilltop carries six of the ten sales and prices the top of the record; Monteleone Avenue below it carries three and prices the bottom, and Myrtle Court one. The lots are zero-lot-line by a secondary source’s description, about 4,800 square feet at the median, and the hilltop lots have the views. A secondary source notes a central park and an elementary school within the community and no Mello-Roos assessment.

The first reason is the hilltop, with the views and the seclusion that the flat tracts do not have. The second is the house, an early-1990s plan with high ceilings and an open kitchen that needs less than the 1980s tracts. The third is the school and the park inside the tract. The fourth is the fee, small enough to ignore, with no Mello-Roos.

Listings report the fee at $104–$120 a month; the most recent sale, in April 2026, reported $120. The recorded sales report association fees from $104 to $120 a month, with $120 on the most recent sale, in April 2026, 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 — Churchwood Drive, Monteleone Avenue and Myrtle Court — 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.

Oak Hills Elementary and a neighborhood park are inside or beside the tract by a secondary source’s description, Oak Canyon Community Park is a short drive, and the Westlake Village shops on Lindero Canyon Road are a few minutes down the hill. 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 Pointe 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 September 2026, five homes in the tract sold through the MLS, at prices from $1,115,000 to $1,480,000 and a median of $1,275,000. Going back to September 2020, ten sales are on record, from $927,000 to $1,480,000 with a median of $1,115,000. The top of the record is $1,480,000 on Churchwood Drive in December 2025 for a 2,382-square-foot four-bedroom; $1,325,000 on Churchwood Drive in April 2025 for a 2,382-square-foot four-bedroom; $1,275,000 on Churchwood Drive in May 2025 for a 2,095-square-foot three-bedroom. The bottom is $927,000 on Monteleone Avenue in September 2020; $960,000 on Monteleone Avenue in September 2020; $990,000 on Monteleone Avenue in April 2023.

Ten sales in six years from $927,000 to $1,480,000 is one house on two streets: Monteleone Avenue at $927,000 to $990,000 from 2020 to 2023, and Churchwood Drive at $1,275,000 to $1,480,000 in 2025, with the hilltop, the view and the renovation deciding the place in the band. 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 Pointe; 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 1990 to 1993, 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. 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 1990s 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 Estates below, 1989 with the same three plans and a similar fee, which trades at a median of $1,240,000 on a six-sale record with a top of $1,249,900; Hillcrest Pointe’s median is lower and its top is higher, because its record has both the Monteleone Avenue sales and the Churchwood Drive hilltop. Monte Carlo, 1993 to 1994 on the flat, is 1,581- to 2,358-square-foot houses at a median of $1,250,000 with a smaller fee. Montego, 1990 to 1993, is 1,529- to 2,454-square-foot houses on smaller lots at $1,166,500.

Start with the street, since the record prices Churchwood Drive several hundred thousand dollars above Monteleone Avenue for the same plan. Then the lot: the view, the slope behind it and whether a pool fits. Then the house, briefed for the early 1990s, with a plumber asked by name about polybutylene supply lines on the 1990 to 1993 houses. Then the association, from the disclosure package. A buyer who needs a single story should look at Bent Tree or Monte Carlo.

Families first, for the school inside the tract and the courts. Empty nesters second, for a view house with little yard to keep. Buyers moving over from Westlake Village third, on the Westlake side of the district.

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 — $1,480,000 — 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.