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.

Country Highlands was built from 1984 to 1986 as one of the attached communities of the Country tracts on the east side of Oak Park, below Deerhill Park. The county records show about 105 units inside the outline, which matches a secondary source’s count of about 106. The MLS files the sales as Country Highlands condos; the developer is not named in any source Gary Jacobs has been able to verify.

The sale record shows a 1,012-square-foot single-level two-bedroom, a 1,373-square-foot two-level three-bedroom and a 1,449-square-foot two-level three-bedroom. The top is $820,000 on Poppyview Drive in December 2025 for the 1,449, $815,000 on Quarterhorse Lane in October 2025 for the 1,373 and $780,000 on Windmill Lane in April 2024. The bottom is $623,979 on Quarterhorse Lane and $629,000 on Windmill Lane, both in August 2020 for the 1,373-square-foot plan, and $680,000 on Poppyview Drive in October 2022 for the 1,012-square-foot single level. Seven of the twelve sales are three-bedrooms and five are two-bedrooms; four of the twelve are single level, at a median of $722,400.

No plan sheet for Country Highlands 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 1,012 to 1,449 square feet, median 1,373, with three bedrooms in seven of the twelve, two in five, and four of the twelve recorded sales are single story.

Three streets off Oak Hills Drive with the pool and its patio in the middle; the homes are red-tile-roofed and light-stuccoed, and a secondary source notes that they are spaced farther apart than in the community’s other townhome tracts. Deerhill Park and Medea Creek Middle School are a short walk.

The first reason is the price, a three-bedroom in the Oak Park district for $780,000 to $820,000. The second is the single-level plan, which the newer condominiums do not offer. The third is the location beside Deerhill Park and the middle school. The fourth is the spacing between the buildings, more than the other attached tracts have.

Listings report the fee at $463–$514 a month, with $514 on the August 2026 sale. The recorded sales report association fees from $463 to $514 a month, with trash and sewer named in the listings as included. Listings describe the pool, a greenbelt, guest parking, a clubhouse and maintained landscaping in the amenities.

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 it marks all three of this tract’s streets — Quarterhorse Lane, Poppyview Drive and Windmill Lane — as Oak Hills or Brookside Elementary, meaning the assignment depends on the address; confirm it with the district office for the exact unit. 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.

Deerhill Park and its youth sports fields, Medea Creek Middle School and the Medea Creek trail are a short walk, and the Oak Park Plaza is down Kanan Road. 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.

Oak Park has no freeway of its own. Kanan Road runs south to the Ventura Freeway at Agoura Hills in about eight to twelve minutes from most streets, and Lindero Canyon Road runs south to the Lindero Canyon interchange in Westlake Village; the north-side tracts add a few minutes to either. Errands are at the Oak Park Plaza on Kanan Road or in Agoura Hills and Westlake Village; the Westside is forty-five minutes on a good day and ninety on a bad one, and a buyer who commutes should time it at 7:30 in the morning before deciding.

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.

Six townhomes sold through the MLS in the last two years (November 2024 to August 2026), at prices from $699,000 to $820,000 and a median of $726,200. The longer record is twelve sales since August 2020, from $623,979 to $820,000. The top of the record is $820,000 on Poppyview Drive in December 2025 for a 1,449-square-foot three-bedroom; $815,000 on Quarterhorse Lane in October 2025 for a 1,373-square-foot three-bedroom; $780,000 on Windmill Lane in April 2024 for a 1,449-square-foot three-bedroom. The bottom is $623,979 on Quarterhorse Lane in August 2020; $629,000 on Windmill Lane in August 2020; $680,000 on Poppyview Drive in October 2022. Single-story homes account for four of the twelve sales, at a median of $722,400.

Twelve sales in six years from $623,979 to $820,000 is one band that has moved: the 1,373- and 1,449-square-foot three-bedrooms traded at $624,000 to $629,000 in 2020 and at $780,000 to $820,000 in 2024 and 2025. The single level trades a step below the same-size two level. Gary Jacobs keeps the full sale-by-sale history and can say where a given unit sits in it.

No lease is recorded in the MLS sources this guide draws on, so it does not quote a rent. The association’s leasing rules should be read before buying as an investment.

These homes date from 1984 to 1986, 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. 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 other Country tracts and the condominiums. Country Village, 1979 to 1984, is 1,134- to 1,827-square-foot units at a median of $735,000 with a similar fee. Country Meadows I, 1980, is 1,325- to 2,143-square-foot homes at $830,000. Country Meadows II, 1984 to 1986, is small-lot detached houses at $999,000. Capri, 1990 to 1994, is the newer condominium at $745,000 with two pools and tennis courts. Country Highlands is the least expensive of the Country tracts and has the single-level plan that Capri does not.

Start with the association package and the roof and plumbing history of a forty-year-old community. Then the plan, single level or two level, since they trade as different markets. Then the school assignment, because all three streets are marked as either Oak Hills or Brookside and the district decides by address. Then the house, briefed for the mid-1980s, with a plumber asked about polybutylene supply lines.

First-time buyers first. Downsizers second, for the single-level two-bedroom. Investors third, at the lowest three-bedroom price in the district’s attached communities.

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 level, and the top of the record — $820,000 — 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.