Hillsborough is a pocket of about 60 single family homes from the early 1980s tucked into the foothills south of the 101, where the Los Padres Trail trailhead sits a short walk away on Los Padres Drive. Lots run a generous 8,000 to 14,000 square feet, there are no HOA dues, and homes sold for about $1.2M to $1.5M in 2025 and 2026. It suits buyers who want a real yard, a trail nearby and a central Thousand Oaks address without paying for a gate or a clubhouse.
Turn off Moorpark Road onto Los Padres Drive and the valley floor gives way to hillside almost immediately. Hillsborough, Newcastle and Scarborough Streets sit in that slope, and homes along the outer edge of the tract look out at open space and local trailheads. Yet Janss Marketplace and the freeway are a straight shot back up Moorpark Road, which is the whole appeal: a morning hike before work and an easy run for groceries, from the same front door.
| Homes | About 60 single family homes |
|---|---|
| Built | 1981 to 1985 |
| Size | 3 to 4 bedrooms, roughly 1,850 to 2,500 sq ft |
| Lots | Mostly 8,000 to 14,000 sq ft |
| Price range | About $1.2M to $1.5M in 2025 and 2026 |
| HOA | None, no dues |
| Gated | No |
| Schools | Acacia Magnet, Colina Middle, Westlake High |
| Getting around | Los Padres Drive to Moorpark Road, minutes to the 101 and Janss Marketplace |
Life at the edge of the open space
The defining feature of Hillsborough is the trail. The Los Padres Trail begins on Los Padres Drive near Fox Hills Drive, runs about a mile, and connects into the Los Robles Open Space trail system, including the Los Padres Trail and Vista Loop, a 3.4 mile circuit with roughly 570 feet of climb that is popular for hiking, trail running, birding and mountain biking. Living here means that loop is part of your week rather than a weekend outing.
The three streets sit off a single feeder road with hillside beyond them. Homes on the outer edge of the tract have the open space outlook; interior lots trade the view for a more sheltered position. The homes have been in place since the early 1980s, and the lots are large for the era and the price point.
Daily errands are straightforward. Moorpark Road takes you north to Janss Marketplace, the city's original outdoor shopping center, which opened in 1961 and today has roughly 39 stores and services plus a movie theater, and on to the 101. For another hillside option in the city, see our guide to Los Robles Hills Estates.
The homes: early 1980s plans on real lots
Hillsborough was built out between 1981 and 1985 with a mix of single story and two story plans, three and four bedrooms, and roughly 1,850 to 2,500 square feet. At least one home here has been marketed as a single story Tudor Traditional with vaulted ceilings and a brick fireplace, which gives a sense of the era's look. The smallest common plan is a three bedroom, two bath at about 1,850 square feet.
What sets the tract apart at this price is land. Most lots run 8,000 to 14,000 square feet, which is generous for an early 1980s neighborhood. A few listings on Hillsborough Street show square footage above the tract norm; treat the verified range as typical and check any claimed additions against city permit records.
One thing to keep straight: the larger custom homes uphill on Oakhampton Street are Ventana Oaks, a separate and more expensive product, with examples running roughly 3,400 to 5,000 square feet and lots that can approach half an acre. They share the same hillside, but Oakhampton sales are not Hillsborough comps.
No dues, no board: what that really means
Hillsborough has no HOA dues because the original association is no longer active. The city's registry lists it as not active, and current listings show $0 in fees. For many buyers that is a real plus: no monthly check and no architectural committee.
It also means nothing is collectively maintained and there is no body to enforce anything or to fund common area work. Before you treat that as "no rules," have the recorded CC&Rs for the tract pulled and reviewed, because recorded restrictions can still run with the land even after an association stops operating. Confirm who is responsible for any slope behind the home you are considering. The neighborhood is not gated, and there are no shared amenities, so what you see on the lot is what you are buying.
Schools: Acacia, Colina and Westlake High
Hillsborough is in the Conejo Valley Unified School District and currently falls within the boundaries of Acacia Magnet School for Enriched Learning for elementary, Colina Middle School and Westlake High School.
- Acacia Magnet is a K through 5 campus of about 350 students on Norman Avenue, rated A minus by Niche. Because it operates as a magnet, enrollment can involve a district process rather than pure address assignment, so ask the district how that works for your family.
- Colina Middle School serves roughly 830 students in grades 6 through 8 and is described as performing above state averages in core subjects.
- Westlake High School on North Lakeview Canyon Road posts a 98 percent graduation rate, well above the state median.
The district has redrawn boundaries in recent years, so run the exact address through the CVUSD school locator before you write an offer.
Prices, and what to check before you buy
Closed sales in Hillsborough ran from about $1.2M to $1.5M in 2025 and 2026, including $1,416,000 on Hillsborough Street in May 2025 and $1,476,000 on Scarborough Street in September 2026. For context, closings in 2021 and 2023 landed around $1.2M to $1.3M, so values have moved up steadily rather than sharply. You can see how that fits the wider city on our Thousand Oaks home values page.
A few items we would put on every Hillsborough checklist:
- Fire zone and insurance. This is foothill, open space adjacent property, and CAL FIRE's 2025 hazard zone update changed designations in the Conejo Valley. Look up the specific parcel on the CAL FIRE map and shop insurance early, before your contingency period runs out.
- Age of home items. Houses built between 1981 and 1985 deserve a sewer lateral scope, a close look at original plumbing and electrical, and a check of any additions against city permits.
- Tax bill. Read the direct levy lines on a current Ventura County tax bill rather than assuming. Given the build dates we would not expect special assessments, but confirm it.
- The vacant lot. One parcel in the first phase remains unbuilt. If you are looking at a home beside it, ask what could go there.
Who Hillsborough suits
Hillsborough works best for buyers who put a trail, a big lot and a central Thousand Oaks location ahead of gates and amenities. It is a natural fit for hikers and mountain bikers who want the Los Robles trail system close by, and for anyone who has decided an HOA bill is not where they want their money to go.
If you want a newer home, a community pool or a gated entry at a similar price, you will be happier in a different tract. If you want more house on the same hillside, look at Ventana Oaks directly uphill, or compare with Carriage Square Estates. For the full picture of how this pocket compares, browse our Thousand Oaks neighborhood guides.
Owning in Hillsborough
What a typical home costs to own
About $8,438/month
- Principal and interest$7,224
- Property tax (about 1.1% of price, Ventura County)$1,215
- HOANone
Estimate for a $1.32M 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 Hillsborough, and are glad to talk through how it compares.
Thousand Oaks home prices, the last five years
Questions people ask about Hillsborough
Does Hillsborough in Thousand Oaks have an HOA?
No. The original Hillsborough association is no longer active and the city registry lists it as not active, so there are no dues. There is also no board or shared maintenance. Recorded CC&Rs may still exist for the tract, so have them pulled and reviewed before assuming there are no restrictions on additions or exterior changes.
How much do homes in Hillsborough cost?
Homes in Hillsborough sold for about $1.2M to $1.5M in 2025 and 2026, with recorded sales on Hillsborough, Newcastle and Scarborough Streets in that range. Plans run three to four bedrooms and roughly 1,850 to 2,500 square feet. The larger custom homes uphill on Oakhampton Street are Ventana Oaks and price well above this range.
Is Hillsborough gated?
No. Hillsborough is an open neighborhood with no gate and no guard. Its three streets sit off Los Padres Drive at the edge of the foothills, so it feels tucked away without being closed off. A few individual homes in neighboring Ventana Oaks have private gates, but that is per property, not a community gate.
What schools serve Hillsborough?
Hillsborough is in the Conejo Valley Unified School District and currently falls within the boundaries of Acacia Magnet School for Enriched Learning, Colina Middle School and Westlake High School. Acacia is a magnet, so enrollment may involve a district process, and boundaries have shifted in recent years. Confirm the exact address with the CVUSD school locator.
Is Hillsborough the same neighborhood as Ventana Oaks?
No, although they sit on the same hillside off Los Padres Drive. Hillsborough is the lower phase: about 60 homes from 1981 to 1985, roughly 1,850 to 2,500 square feet. Ventana Oaks is the uphill custom section on Oakhampton Street, with homes in the 3,400 to 5,000 square foot range on larger lots and considerably higher prices.
Is there hiking near Hillsborough?
Yes. The Los Padres Trail starts on Los Padres Drive near Fox Hills Drive, runs about a mile and connects into the Los Robles Open Space trail system. It includes the Los Padres Trail and Vista Loop, a 3.4 mile moderately difficult loop with about 570 feet of climb that is popular for hiking, birding and mountain biking, with dogs allowed on leash.
Thinking about Hillsborough?
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 HOA registry
- City of Thousand Oaks parcel layer
- Conejo Valley Unified School District school locator
- CAL FIRE Fire Hazard Severity Zone maps
- Westlake High School, U.S. News
- Acacia Magnet School, NCES
- Colina Middle School, GreatSchools
- Los Padres Trail, Conejo Valley Guide
- Los Padres Trail and Vista Loop, AllTrails
- Janss Marketplace
Facts checked October 2026.
