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.

Shadow Oaks was built in 1989 beside the much larger Shadow Ridge condominiums, which followed in 1990, and a secondary source names Lennar Homes as the builder, the only tract in this guide series for which a builder is named in any source. The county records show about 81 units inside the outline, which matches the same source’s count of about 80. The MLS files the sales as Shadow Oaks.

The sale record shows two plans, 1,204 and 1,236 square feet, both two-bedroom and both on two levels with a suite and bath for each bedroom upstairs. The top is $710,000 on Water Oak Lane in June 2026, $709,000 on Spanish Oak Lane in May 2025 and $699,000 on Riodosa Trail in July 2025, all for the 1,204. The bottom is $505,000 on Spanish Oak Lane in April 2020 for the 1,236, and $600,000 and $607,000 on Spanish Oak Lane in July 2026 and August 2022. Every one of the eleven sales is a two-bedroom. A secondary source notes that the homes are mostly all-electric, that the downstairs can be dark and that some garages lack direct access to the unit.

No plan sheet for Shadow Oaks 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 1,204 to 1,236 square feet, median 1,204, with two bedrooms in eleven of the eleven, and every recorded sale is two story.

Three short streets under mature trees, with Spanish Oak Lane carrying six of the eleven sales and Water Oak Lane four; the pool, spa and clubhouse are among the buildings. A secondary source calls Shadow Oaks the sister community to Shadow Ridge, with a less crowded feel. The Medea Creek trail and the Oak Park community center are close.

The first reason is the price, a two-bedroom townhome with a garage in the Oak Park district for $600,000 to $710,000. The second is the plan, two suites upstairs, which works for roommates, a couple and a home office, or a parent and an adult child. The third is the fee, high but carrying water, sewer, trash and earthquake insurance in the listings that name them.

Listings report the fee at $619–$698 a month, with $694 to $698 on the mid-2026 sales. The recorded sales report association fees from $619 to $698 a month, with water, sewer, trash, earthquake insurance and the clubhouse named in various listings as included. Listings describe the pool and spa, a clubhouse, a fitness room, guest parking 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 every street in this tract’s sale record — Spanish Oak Lane, Water Oak Lane and Riodosa Trail — 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.

The Medea Creek trail and the Oak Park community center are close, Medea Creek Middle School is up Doubletree Road, 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 July 2026, 7 homes in the tract sold through the MLS, at prices from $600,000 to $710,000 and a median of $675,000. Over the longer record, eleven sales from April 2020 through July 2026 ran from $505,000 to $710,000 with a median of $665,000. The top of the record is $710,000 on Water Oak Lane #B in June 2026 for a 1,204-square-foot two-bedroom; $709,000 on Spanish Oak Lane #C in May 2025 for a 1,204-square-foot two-bedroom; $699,000 on Riodosa Trail #D in July 2025 for a 1,204-square-foot two-bedroom. The bottom is $505,000 on Spanish Oak Lane #G in April 2020; $600,000 on Spanish Oak Lane #C in July 2026; $607,000 on Spanish Oak Lane #B in August 2022.

Eleven sales in six years from $505,000 to $710,000 is one plan that has moved: $505,000 in 2020, $600,000 to $607,000 for the unrenovated units and $699,000 to $710,000 for the renovated ones since 2025. 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 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. 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 Shadow Ridge next door, 1990, the largest condominium community in Oak Park with one- and two-bedroom units of 780 to 1,244 square feet at a median of $470,000 and fees near $580 a month; Shadow Oaks is the smaller, quieter and slightly dearer sister. Capri, 1990 to 1994 on the west side, is 1,240- to 1,643-square-foot units at $745,000 with two pools and tennis courts. Country Village, 1979 to 1984, is 1,134- to 1,827-square-foot units at $735,000. Shadow Oaks is the least expensive two-bedroom townhome with a garage in the community after Shadow Ridge.

Start with the association package and the roof, plumbing and exterior history of a community from 1989, and read what the fee carries, since it is one of the highest in Oak Park. Then the unit: the light downstairs, the garage access and the all-electric systems that a secondary source flags. Then the position, near the pool or away from it. Then the school assignment, confirmed for the exact unit.

First-time buyers first. Investors second, for a two-suite plan near $650,000. Downsizers third, from the Oak Park houses, who want to stay in the community.

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 — $710,000 — 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.