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.

Rolling Hills Estates was built in 1988 and 1989 on the slope south of Doubletree Road, one of the last of the second-wave tracts and the largest-house tract on the east side before Regency Hills and Chambord a decade later. The county records show about 137 parcels inside the outline, which matches a secondary source’s count of about 140. The MLS files the sales as Rolling Hills Estates; the developer is not named in any source Gary Jacobs has been able to verify.

The sale record shows a 1,860-square-foot single-story three-bedroom and a 3,048- to 3,136-square-foot two-story four-bedroom, with the larger plan accounting for seven of the nine sales. The top is $1,600,000 on Countryside Road in November 2023 for the 3,136, $1,387,170 on Sunnycrest Drive in January 2024 for the 3,048 and $1,290,000 on Southridge Drive in October 2020 for the 3,136. The bottom is $1,000,000 on Southridge Drive in May 2026 for the single story, $1,100,000 on Sunnycrest Drive in February 2023 and $1,150,000 on Sunnycrest Drive in September 2020 for the larger plans. Seven of the nine sales are four-bedrooms and two are three-bedrooms; two are single story. A secondary source describes the tract as having some of the largest houses in Oak Park for its price.

No plan sheet for Rolling Hills 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 1,860 to 3,136 square feet, median 3,048, with four bedrooms in seven of the nine, three in two, and two of the nine recorded sales are single story.

Southridge Drive and Sunnycrest Drive carry three sales each, Medea Creek Lane two and Countryside Road one. The lots run about 5,300 to 8,500 square feet, median about 6,400, on a slope that a secondary source says faces south toward the Santa Monica Mountains, with a mature tree canopy. The Medea Creek trail runs along the bottom of the tract and Doubletree Road along the top, with Medea Creek Middle School across it.

The first reason is the square footage for the money: a 3,000-square-foot four-bedroom in the district for $1,400,000 to $1,600,000, which nothing else in Oak Park matches. The second is the absence of a fee. The third is the slope and the view south. The fourth is the middle school across the road.

No association fee appears in any of the nine recorded sales, and two secondary sources agree that Rolling Hills Estates has no homeowners association.

No association fee appears in the recorded sales, which means the constraint on an owner is the city and county permit process rather than an architectural committee. Confirm with the title report that no association or CC&Rs attach to the specific parcel.

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: it assigns Southridge Drive and Countryside Road to Red Oak Elementary, and splits Sunnycrest Drive and Medea Creek Lane by address, with 6094 Sunnycrest and below and 300 Medea Creek Lane and up to Red Oak and 6240 Sunnycrest and up and 218 Medea Creek Lane and below to Brookside. The recorded sales on Sunnycrest Drive are all in the Red Oak range. Confirm the assignment with the district office for the exact house. 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.

Medea Creek Middle School is across Doubletree Road, the Medea Creek trail is at the bottom of the tract, Deerhill Park and Oak Canyon Community Park are a short drive, 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.

In the two years through August 2026, 2 homes in the tract sold through the MLS, at $1,000,000 and $1,185,000. Over the longer record, nine sales from July 2020 through August 2026 ran from $1,000,000 to $1,600,000 with a median of $1,185,000. The top of the record is $1,600,000 on Countryside Road in November 2023 for a 3,136-square-foot four-bedroom; $1,387,170 on Sunnycrest Drive in January 2024 for a 3,048-square-foot four-bedroom; $1,290,000 on Southridge Drive in October 2020 for a 3,136-square-foot four-bedroom. The bottom is $1,000,000 on Southridge Drive in May 2026; $1,100,000 on Sunnycrest Drive in February 2023; $1,150,000 on Sunnycrest Drive in September 2020. Single-story homes account for two of the nine sales, at a median of $1,185,000.

Nine sales in six years from $1,000,000 to $1,600,000 is one plan and one exception: the 3,048- to 3,136-square-foot four-bedroom, at $1,100,000 to $1,290,000 from 2020 to 2023 and $1,387,170 to $1,600,000 since, and the 1,860-square-foot single story at $1,000,000 in 2026. The renovation and the view decide 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 Rolling Hills Estates; a current figure should come from the leasing agents who work these streets. A detached house in this district at this size is a scarce rental, and the tenants it draws are families relocating for the schools who want a year or two to buy.

These homes date from 1988 to 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 by size, and Rolling Hills Estates is the least expensive 3,000-square-foot house in Oak Park. Morrison Estates and Sutton Valley, 1986 to 1989 on the north side, is 2,502- to 4,315-square-foot houses on quarter-acre lots at a median of $2,000,000. Regency Hills, 1997 to 1999, is 2,614- to 3,716-square-foot houses at $1,825,000. Bent Tree, 1987 to 1988 without a fee, is 1,950- to 2,815-square-foot houses at $1,400,000. Rolling Hills Estates gives the square footage of Regency Hills on the lot of Bent Tree, with no fee, at a median of $1,185,000.

Start with the house, because a secondary source says some are updated and others are not, and the record prices the difference at several hundred thousand dollars; brief the inspector for 1988 and 1989 and ask a plumber by name about polybutylene supply lines. Then the lot and the slope, with the drainage and the view. Then the school assignment, because two of the four streets are split by address. Then the title report, to confirm that no association or CC&Rs attach to the parcel.

Families who need the fifth bedroom or the bonus room first, at the lowest price for the size in Oak Park. Buyers moving up from the smaller east-side tracts second. Buyers who want no association third.

For a buyer, read the plan off the square footage and the level, walk the lot before the house, 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 — $1,600,000 — 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.