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.

Monte Carlo was built in 1993 and 1994, the last of the three Italian-named tracts on the west side of Kanan Road and one of the last detached tracts in Oak Park before Regency Hills and Chambord on the east side. The county records show about 156 parcels inside the outline, which matches a secondary source’s count of about 155. The MLS files the sales as Monte Carlo; the developer is not named in any source Gary Jacobs has been able to verify.

The sale record shows a 1,581-square-foot single-story three-bedroom, a 1,984- to 2,019-square-foot two-story four-bedroom and a 2,358-square-foot two-story five-bedroom, with vaulted entries and mountain views from some lots by a secondary source’s description. The top is $1,450,000 on Pesto Way in September 2025 for the 2,358 and $1,450,000 on Pesto Way in July 2022 for the 2,019, and $1,410,000 on Pesto Way in August 2026 for the 1,984. The bottom is $950,000 on Carmento Drive and $950,000 on Cremona Way in 2020, and $1,105,000 on Pesto Way in October 2025 for the single story. Five of the eleven sales are four-bedrooms, four are five-bedrooms and two are three-bedrooms; two are single story, at a median of $1,160,000.

No plan sheet for Monte Carlo 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 1,581 to 2,358 square feet, median 1,984, with four bedrooms in five of the eleven, five in four, three in two, and two of the eleven recorded sales are single story.

Pesto Way carries five of the eleven sales, with Cremona Way and Anzio Way two each and Savoy Court and Carmento Drive one. The lots run about 4,300 to 7,900 square feet, median about 5,700, and a secondary source counts several private pools among them, though it calls the yards small. Indian Springs Park and Red Oak Elementary are a few blocks away.

The first reason is the house, the newest production plan on the west side, with the vaulted entry and the open kitchen that the 1980s tracts do not have. The second is the single-story plan. The third is the location, a few blocks from the school and the park in what a secondary source calls one of the most family-friendly tracts in Oak Park. The fourth is the fee, small enough to ignore.

Listings report the fee at $75–$95 a month, and every sale since 2022 reported $95. The recorded sales report association fees from $75 to $95 a month, and listings describe a greenbelt and maintained landscaping in the amenities. One secondary source gives about $95 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 — Pesto Way, Cremona Way, Anzio Way, Savoy Court and Carmento Drive — is assigned to Red Oak 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.

Indian Springs Park, with its ball fields, tennis and basketball courts and playground, and Red Oak Elementary are a few blocks away, and the Oak Park Plaza is at the bottom of 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, seven homes in the tract sold through the MLS, at prices from $1,105,000 to $1,450,000 and a median of $1,288,000. Over the longer record since June 2020, eleven sales ran from $950,000 to $1,450,000 with a median of $1,250,000. The top of the record is $1,450,000 on Pesto Way in September 2025 for a 2,358-square-foot five-bedroom; $1,450,000 on Pesto Way in July 2022 for a 2,019-square-foot four-bedroom; $1,410,000 on Pesto Way in August 2026 for a 1,984-square-foot four-bedroom. The bottom is $950,000 on Carmento Drive in June 2020; $950,000 on Cremona Way in July 2020; $1,105,000 on Pesto Way in October 2025. Single-story homes account for two of the eleven sales, at a median of $1,160,000.

Eleven sales in six years from $950,000 to $1,450,000 is one band that has moved: $950,000 in 2020 and $1,410,000 to $1,450,000 for the two-story plans since 2022, with the single story at $1,105,000 to $1,215,000 below it. The renovation and the pool 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 Monte Carlo; 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 1993 to 1994, 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 the tracts around it. Monaco next door, 1989 to 1992 without a fee, is 1,694- to 2,387-square-foot houses at a median of $1,175,000 with no single story. Bent Tree, 1987 to 1988 without a fee, is larger houses at $1,400,000. Hillcrest Pointe, 1990 to 1993 on the hilltop, is 2,041- to 2,382-square-foot houses at $1,115,000. Monte Carlo is the newest of the four and the one with the single-story plan, and it trades at the top of the group with Bent Tree.

Start with the plan and the level, since the single story trades below the two-story plans. Then the yard, which is small; a pool fits on some lots and not others. Then the house, briefed for 1993 and 1994, with a plumber asked by name about polybutylene supply lines. Then the association, from the disclosure package.

Families with children at Red Oak first. Buyers who want a single story second. Buyers moving up from Capri or the condominiums third, who want a house without leaving the west side.

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 level, and the top of the record — $1,450,000 — 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.