Ventana Oaks is a pocket of about 27 custom homes on half acre and larger lots, tucked into the oak-covered hillside above Los Padres Drive on the south side of the 101 in Thousand Oaks. It suits buyers who want land, privacy and a real custom house without association dues or gatehouse rules, and who are patient, because only two homes have sold since 2024. Expect about $1.8M to $2.7M in 2024 and 2026 for 3,500 to 5,000 square feet.
Turn off Los Padres Drive, climb through Hillsborough, and the streets go quiet. Oakhampton and the upper end of Scarborough include cul-de-sac ends, the lots open up to half an acre and more, and mature oaks hang over long driveways, many of them behind their own gates. Nobody built these houses to a single plan. A Tudor sits a few doors from a Spanish tile roof, which sits near a Traditional with a pool under the trees, and that mix is the whole point of Ventana Oaks.
| Homes | About 27 custom homes |
|---|---|
| Built | 1982 to 1990 |
| Size | 4 to 5 bedrooms, about 3,500 to 5,000 sq ft |
| Lots | Roughly half acre to nearly an acre |
| Price range | About $1.8M to $2.7M in 2024 and 2026 |
| HOA | None |
| Gated | No, though many homes have private driveway gates |
| Schools | Acacia Magnet, Colina Middle, Westlake High |
| Getting around | Moorpark Road to the 101, Los Padres trailhead at the bottom of the hill |
What daily life feels like up here
This is a hillside enclave, not a planned community. The streets sit directly uphill from Hillsborough, and you reach them the same way: Moorpark Road south from the 101, left on Los Padres, right on Hillsborough and up onto Scarborough or Oakhampton. Once you are up, the cul-de-sac ends keep through traffic to a minimum.
The lots are the story. At roughly 20,000 to 40,000 square feet, there is room for a pool and spa, a long gated drive, a side yard that is actually a yard, and the mature oaks that shade these streets. Several owners have held their homes for decades, and that shows in how settled the streets feel. Homes come to market rarely.
The homes: custom builds, not a tract product
Ventana Oaks was built out between 1982 and 1990, and the houses read as individual custom builds rather than a single builder's line. Styles genuinely vary. Tudor and French-influenced designs, Spanish homes with tile roofs, and Traditional two-stories all appear within a short walk of each other.
- Size: four and five bedrooms, roughly 3,500 to 5,000 square feet.
- Layouts: floor plans vary house by house, and at least one home here was built with a first-floor primary suite.
- Grounds: pools, spas and park-like yards under mature oaks appear on several of these properties.
- Privacy: individual driveway gates are frequent. When a listing here says gated, it means the home, not the neighborhood.
Because each house is different, condition and updates drive value as much as square footage. A fully renovated home and a largely original mid-1980s interior can sit on the same street at very different prices.
Schools
Ventana Oaks is in the Conejo Valley Unified School District. The assigned schools are Acacia Magnet School for Enriched Learning, Colina Middle School and Westlake High School. Acacia operates as a magnet program, so families should confirm enrollment details directly with the district before relying on the assignment.
Trails, the freeway and what sits nearby
The Los Padres Trail begins on Los Padres Drive near Fox Hills Drive, a short way down the hill. It runs about a mile and links into the Los Robles Trail, and it is maintained by the Conejo Open Space Foundation, so a morning hike or dog walk starts close to your own street rather than across town. Hikers park on the street at the trailhead, which is worth knowing on busy weekends.
The 101 is reached via Moorpark Road, with shopping and restaurants near the corridor. For buyers comparing hillside custom pockets on this side of town, Los Robles Hills Estates and Carriage Square Estates are natural alternatives, and our Thousand Oaks neighborhoods page lays them all out.
Prices, and why the comps are thin
Two homes have closed since 2024, one at about $2.7M in early 2024 and one at about $1.8M in early 2026. That spread reflects size and condition more than a market move, and it is the reality of a roughly 27-home pocket: there is no steady stream of sales to set a clear line.
Appraisers will reach into Hillsborough directly below, where homes trade materially lower. Buyers need to understand that difference going in, and sellers need an agent who can document why the hillside lots command a premium. Our Thousand Oaks home values page gives the wider context.
Who it suits, and what to check before buying
Ventana Oaks fits buyers who want a true custom home on real land, who value privacy over amenities, and who prefer no association. It is less of a fit for anyone who wants a gatehouse, shared facilities, or a predictable product where every house is comparable.
- No HOA cuts both ways. No dues, but also no architectural review, no shared slope maintenance and no reserves. Oak care and hillside upkeep are yours.
- Search both spellings. The name is sometimes spelled Vantana Oaks. Searching only Ventana will miss part of the sales history.
- Inspect the custom work. Homes of this age and type often carry additions and owner-driven changes. Permits and a thorough inspection matter more here than in a tract.
- Be patient. With only two sales since 2024, the right house may take a year or more to surface.
Owning in Ventana Oaks
What a typical home costs to own
About $13,693/month
- Principal and interest$11,722
- Property tax (about 1.1% of price, Ventura County)$1,971
- HOANone
Estimate for a $2.15M home, near the middle of the recent range here, with 20% down at 7.24% (30 year fixed, Freddie Mac, October 29, 2026). Homeowners insurance is extra and varies with fire zone, so get a quote early. Your lender's figures will differ.
Thousand Oaks market, latest data
- Median sale price$1.13M
- Change over 12 months-5.0%
- Typical days on market34
Citywide, three months ending May 2026. Thousand Oaks home values
Our experience here
We sell across this part of the Conejo Valley, including the neighborhoods around Ventana Oaks, and are glad to talk through how it compares.
Thousand Oaks home prices, the last five years
Questions people ask about Ventana Oaks
Is Ventana Oaks a gated community?
No. Ventana Oaks is an open hillside neighborhood with no gatehouse or shared entry. Many individual homes have private driveway gates, which is why listings often use the word gated. That refers to the property, not the street or the neighborhood.
Does Ventana Oaks have an HOA?
No. There is no active homeowners association and no dues. Owners handle their own landscaping, slopes and oak trees, and there is no architectural review process. Buyers who want that freedom appreciate it; those who want shared standards should look at an association-managed community instead.
How much do homes in Ventana Oaks cost?
Homes have sold for about $1.8M to $2.7M in 2024 and 2026, for four and five bedroom custom houses of roughly 3,500 to 5,000 square feet on half acre and larger lots. Condition and renovation level drive the spread as much as size, since each house was built individually.
What schools serve Ventana Oaks?
The assigned schools are Acacia Magnet School for Enriched Learning, Colina Middle School and Westlake High School, all in the Conejo Valley Unified School District. Because Acacia is a magnet program, confirm enrollment details with the district before you buy.
How does Ventana Oaks compare to Hillsborough?
Hillsborough sits directly below on the same hillside and sells for well under Ventana Oaks pricing; its median sale price has run near $1.4M. Ventana Oaks is the custom upper tier: larger houses, half acre and bigger lots, and far fewer sales, with only two closings since 2024.
Why do some listings spell it Vantana Oaks?
Both spellings circulate, and they refer to the same small pocket of about 27 homes on Oakhampton and upper Scarborough. Marketing copy commonly uses Ventana, while Vantana shows up elsewhere. When researching sales history, search both spellings or you will see only part of the picture.
Thinking about Ventana Oaks?
Whether you are weighing a move here or wondering what your home would bring, Davis and the team are happy to talk it through, street by street. No obligation.
Sources
- City of Thousand Oaks parcel data
- City of Thousand Oaks HOA registry
- Conejo Valley Unified School District attendance boundaries
- Redfin Hillsborough neighborhood market data
- Conejo Valley Guide, Los Padres Trail
- DogTrekker, Los Padres Trail to Los Robles Trail
- Compass listing detail, Scarborough Street
- Berkshire Hathaway listing detail, Oakhampton Street
- Estately listing detail, Oakhampton Street
- Homes.com listing detail, Scarborough Street
Facts checked October 2026.
