No plan sheet for Montego 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 sorts into two plans: the three-bedroom, five of the thirteen sales, from 1,529 to 1,890 square feet; and the four-bedroom, eight sales, from 2,035 to 2,454, with the 2,216- to 2,247-square-foot version the most common house in the tract. The four-bedrooms have sold from $920,000 in 2020 to $1,385,000 in 2026; the three-bedrooms from $1,000,000 to about $1,150,000.

Saint Croix Court carries the most sales, with Ocho Rios Way, Valero Circle, Saint Thomas Drive and Bayport Way behind it. The top of the record is on Ocho Rios Way and Bayport Way: $1,385,000 in April 2026, $1,370,000 in December 2024 and $1,290,000 in April 2024, all 2,216- to 2,247-square-foot four-bedrooms. The lots are close enough in size that the street does not sort the price; the plan and the condition do.

About 3,800 square feet at the median is a yard for a patio, a lawn and a play structure, not a pool, and the houses sit close enough together that the side yards are walkways. That is the trade for the price: a detached house with a two-car garage in the Oak Park district at about $1,175,000 rather than $1,825,000 in Regency Hills or $2,000,000 in Morrison Estates. Buyers who need more yard than that should look at Rolling Hills Estates or Bent Tree, the late-1980s tracts on lots around 6,000 with no fee, or accept the price step to the large-lot tracts.

The first reason is the price for a detached house in the district: a four-bedroom with a two-car garage at a median of $1,170,000, when the large-lot tracts start at $1,800,000. The second is the house itself, an early-1990s plan with a family room, a real primary suite and modern glazing that the 1970s tracts do not have. The third is the Red Oak assignment with no ambiguity in the street list. The fourth is the location, on the Westlake Village side of the community with the shopping center close by.

2026 sales show the Montego fee at $120 a month; listings since 2020 have reported $110 to $125 a month, and the amenities they carry are a playground, picnic area, barbecue, greenbelt and guest parking. The scale suggests an association that keeps the park and the common landscaping and holds an architectural say over exteriors; what it actually 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 and the CC&Rs from the seller’s disclosure package and read them before removing a contingency.

For underwriting, $120 a month is a small line. The practical effect of the association is on exteriors and on any addition: with lots this size, a room addition or a second-story deck is close to the neighbors and will go through both the county and the association.

Montego is in the Oak Park Unified School District, a small independent K–12 district that is one of the main reasons buyers choose Oak Park. The district publishes an elementary boundary street list, and every street in this tract’s sale record — Saint Croix Court, Ocho Rios Way, Valero Circle, Saint Thomas Drive, Bayport Way and Barbados Court — 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.

Montego is on the west side of Oak Park off Lindero Canyon Road, which puts the Kanan and Lindero Canyon shopping center — the supermarket, restaurants and everyday services — a few minutes away, and Westlake Village’s shopping a few minutes beyond it. The tract’s own playground and picnic area are the everyday amenity, and Oak Canyon Community Park is nearby. The Ventura Freeway is reached down Lindero Canyon Road to Westlake Village, about eight to ten minutes in normal traffic.

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 April 2026, 6 homes in the tract sold through the MLS, at prices from $1,059,000 to $1,385,000 and a median of $1,170,000. The top three — $1,385,000 on Ocho Rios Way in April 2026, $1,370,000 on Bayport Way in December 2024, $1,290,000 on Ocho Rios Way in April 2024 — are the 2,216- to 2,247-square-foot four-bedroom, renovated. The bottom is the 2020 baseline, $920,000 for a 2,035-square-foot four-bedroom on Saint Croix Court, and the smallest three-bedroom at $1,000,000 on Valero Circle in May 2023.

The shape of the six years is the same as the rest of Oak Park: a jump from 2020 into 2022 and a band since, with the premium inside the band going to the four-bedroom plan and the renovation. A four-bedroom that sold for $920,000 in 2020 has traded at $1,290,000 to $1,385,000 since 2024 in renovated condition. Against its 1990s neighbors, Montego trades a little below Monte Carlo, whose slightly larger houses on slightly larger lots have a median of $1,288,000, and above Hillcrest Pointe at $1,075,000.

These houses are thirty to thirty-five years old, and the early-1990s list is a specific one: original furnaces, water heaters and condensers at end of life; tile-roof underlayment approaching the end of its span; original dual-pane windows with failed seals; and, for the years 1990 to 1993 in particular, the possibility of polybutylene supply lines, which a plumber should be asked about by name. Small lots put the drainage close to the house, so ask about grading and any history of water at the foundation. None of this is unusual; all of it is negotiable if it is found before the contingency comes off rather than after.

No lease is recorded in the MLS sources this guide draws on, so it does not quote a rent for the tract; a current figure should come from the leasing agents who work these streets. A four-bedroom detached house in the Oak Park district at this size is a natural rental for a family relocating for the schools, and the association’s leasing rules should be read before buying as an investment.

Start with the lot, because it is the constraint: walk the yard and decide whether 3,800 square feet is enough. Then the plan, three-bedroom or four. Then the house, with the inspector briefed on the early-1990s list and asked by name about polybutylene. Then the association, from the disclosure package. A buyer who needs a single story should look elsewhere; every recorded sale here is two story.

Young families first, for whom Montego is the first detached house in the district after a townhome in Country Vista or Capri, or a move from the San Fernando Valley. Buyers relocating for the schools second, who want a house that needs little work at a price under $1,400,000. Downsizers rarely, because there is no single story.

The comparisons that matter are the other 1990s small-lot tracts on the west side. Monte Carlo, 1993 to 1994 on Pesto Way, Cremona Way and Anzio Way, is 1,581- to 2,358-square-foot houses on lots around 5,700 square feet at a median of $1,288,000 with a fee of $75 to $95 a month. Hillcrest Pointe, 1989 to 1993 on Churchwood Drive and Monteleone Avenue, is 2,041- to 2,382-square-foot houses on lots around 4,400 at a median of $1,075,000 with a fee of $104 to $120. Capri West Oaks Park, 1990 to 1994, is the attached version: 1,240- to 1,643-square-foot townhomes at a median of $750,000 with dues of $368 to $515. Montego sits between Hillcrest Pointe and Monte Carlo on price with the smallest lots of the three detached tracts.

For a buyer, read the plan off the square footage, walk the yard, and brief the inspector on the early-1990s list. Pull the permit history of any addition from the county, because on lots this size additions are close to the line. Take the fee and the CC&Rs from the disclosure package.

For a seller, the comparable is the same plan, and the top of the record — $1,385,000, $1,370,000, $1,290,000 — is the four-bedroom, renovated. If the kitchen, the baths and the floors are done, price to those; if not, price to the $1,100,000 to $1,200,000 band and let the plan argue for the top of it. Say Red Oak in the listing; it is the first question.

Oak Park is an unincorporated community of Ventura County, built out as a sequence of tracts from the late 1960s to the early 2000s under the county’s planning. The early 1990s were the decade of the small-lot detached tract on the west side, off Lindero Canyon Road: Montego, Monte Carlo, Monaco, Capri and Hillcrest Pointe, each named for somewhere warmer than Ventura County and each built to a handful of two-story plans on lots of 3,500 to 6,000 square feet. Montego, 1990 to 1993 in the recorded sales, is the one with the Caribbean names.

The builder is not named in any source Gary Jacobs has been able to verify, and this guide does not guess. What the sale record shows is a tract of a consistent product: a three-bedroom of about 1,530 to 1,890 square feet and a four-bedroom of about 2,035 to 2,454, all two story, on lots that are small by Oak Park standards and were meant to be.