Rolling Oaks is 56 custom homes on two to three acre lots tucked south of Hillcrest Drive, where barns, arenas and oak trees set the tone and the old association no longer collects a dime. It suits buyers who want horses, privacy and room to build, and who are comfortable with county rules rather than city ones. The last homes to change hands, in 2021 and 2022, sold for about $1.6M to $2.2M, and nothing has traded since, so expect any current sale to set its own price.
Turn off Hillcrest Drive onto Rimrock Road and the city falls away. The lots stretch to three acres, and the sound is hooves on an arena and wind in the oaks rather than traffic. Most of Rolling Oaks sits just outside Thousand Oaks city limits in unincorporated Ventura County, which is part of why it has stayed this way for decades.
| Homes | About 56 custom homes, each built separately |
|---|---|
| Built | 1956 to 2019, with clusters in the early 1960s and 2000 to 2007 |
| Price range | About $1.6M to $2.2M at the last sales in 2021 and 2022; no sales since |
| Lots | Two to three acres is typical, median about 2.9 acres; some over four |
| HOA | None; the original association is disbanded |
| Jurisdiction | Mostly unincorporated Ventura County, a few lots inside the city |
| Schools | Conejo Academy, Colina Middle, Westlake High |
| Getting around | US-101 at Westlake Boulevard via Hillcrest Drive |
Horse country off Hillcrest Drive
Rolling Oaks runs along Rimrock Road, Sundown Road, Colt Lane and Saddle Trail, with Haaland Drive, East Rolling Oaks Drive and South Rancho Road filling in the edges. The street names tell you the character. Properties here are zoned and used for horses, with stables, corrals and riding arenas on the larger lots, and some back directly onto preserved open space and equestrian trails.
Turnover is close to nil. Owners buy for the land and stay for decades, so the neighborhood feels settled and private in a way that the newer estate tracts around Thousand Oaks cannot quite match. You will see a 1960s ranch house next to a 2005 custom build, and nobody seems to mind.
The homes: no two alike
Because every home was built one at a time by its owner rather than by a tract builder, the range is wide. The modest end is a 1,600 square foot ranch house from the early 1960s sitting on nearly three acres. The upper end is 7,000 to 8,000 square feet with six or seven bedrooms, styled anywhere from traditional ranch to custom Tuscan. Pools, barns, guest structures and arenas are common on the bigger lots.
What they share is land. Two to three acre lots are the norm, the median is about 2.9 acres, and a few exceed four. That is rare in the Conejo Valley, and it is the real asset here. A dated house on three acres is a project with an upside; the lot does not get smaller.
One note for map readers: the Novella homes on Blake Ridge Court were carved out of this area in 2005 and are a different product, newer and on smaller lots. They are neighbors, not part of Rolling Oaks.
What it costs, and why the number is slippery
The last two sales inside Rolling Oaks closed in 2021 and 2022 at roughly $1.6M to $2.2M, one a small older ranch house on acreage and the other a large 1990s estate. Since then, nothing has sold. Fifty-six homes with owners who rarely move will do that.
Practically, that means there is no reliable recent median, and any figure you see quoted online is a model rather than a transaction. When a home does list, pricing will lean on older Rimrock Road history and on nearby estate pockets. Appraisals can lag in that situation, so a buyer with a large loan should plan for a possible gap. For broader context on where the city's prices sit, see our Thousand Oaks home values page, and compare with our guides to Hillsborough and Ventana Oaks if you are weighing nearby neighborhoods.
Schools: a language immersion elementary at the corner
Rolling Oaks is in the Conejo Valley Unified School District. The assigned elementary is Conejo Academy of Leadership and Language Immersion, a small TK through 5 campus on Conejo School Road, with roughly 258 students and about an 18 to 1 student to teacher ratio. Its test score rankings sit in the lower band for California elementary schools, which is worth knowing up front; the district's open enrollment process gives families other options.
Middle school is Colina Middle on Hillcrest Drive, and high school is Westlake High. Because this pocket straddles the city line and sits near boundary edges, confirm the assignment for the specific home with the district before you count on it.
Getting around and what is nearby
Freeway access is the 101 at Westlake Boulevard, reached by Hillcrest Drive, which also connects you to the Civic Arts Plaza and The Lakes at Thousand Oaks, the lifestyle center with dining and shopping around a landscaped lake. The Lakes is in the middle of a tenant refresh, with Erewhon and PopUp Bagels among the arrivals.
The bigger draw is outdoors. Thousand Oaks protects nearly 15,250 acres of open space, and the Conejo Open Space Conservation Agency maintains more than 150 miles of hiking, biking and equestrian trails. For a rider or hiker in Rolling Oaks, some of that network starts at the back fence.
Before you buy: county land, fire and no rulebook
- Jurisdiction. Roughly three in four lots sit in unincorporated Ventura County, the rest inside the city, and two neighbors on the same street can fall on different sides. The mailing address says Thousand Oaks either way. Permits, zoning, code enforcement and ADU rules follow the county for most homes here, so confirm which agency governs a property before planning a remodel, a barn or a second unit.
- No HOA. The original association is disbanded, so there are no dues, no architectural committee and no common area. The flip side is no one to enforce against a neighbor's RV, paint color or barn. Have title check for any surviving recorded covenants or shared road and easement maintenance agreements.
- Fire. Thousand Oaks carries some of the most very high fire hazard acreage in Ventura County on the current state maps. Sellers in those zones have had added disclosure duties since July 2021, and defensible space documentation is expected. Get insurance quotes during the contingency period, not after.
- Utilities and animals. Rural acreage varies on sewer versus septic, district water versus well, and propane versus gas; check each property. Horse keeping is established here, but permitted animal counts and barn setbacks run off county zoning.
For how Rolling Oaks compares to the rest of the city, browse our Thousand Oaks neighborhoods index.
Owning in Rolling Oaks
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 Rolling Oaks, and are glad to talk through how it compares.
Thousand Oaks home prices, the last five years
Questions people ask about Rolling Oaks
Is Rolling Oaks actually in Thousand Oaks?
Mostly not, in the legal sense. The address is Thousand Oaks 91361, but about three quarters of the lots sit just outside city limits in unincorporated Ventura County, with the rest inside the city. That affects permitting, zoning and some services, so confirm the jurisdiction for any specific home.
Does Rolling Oaks have an HOA?
No. The Rolling Oaks association is disbanded, so there are no dues, no design review and no common area maintenance. Buyers should still have title check for any recorded covenants or private road agreements that may still run with the land.
Can I keep horses in Rolling Oaks?
Yes, it is established horse country. Properties are zoned for horses, and stables, corrals and arenas are common on the two to three acre lots, with some backing to equestrian trails. Permitted animal counts and barn setbacks follow county zoning, so verify for the exact property.
How much do homes in Rolling Oaks cost?
The last two sales, in 2021 and 2022, closed at about $1.6M to $2.2M, spanning a small 1960s ranch house on acreage to a large 1990s estate. Nothing has sold since, so there is no current median; the next listing will set its own price against Rimrock Road history and nearby estate pockets.
What schools serve Rolling Oaks?
Conejo Academy of Leadership and Language Immersion for TK through 5, Colina Middle on Hillcrest Drive, and Westlake High, all in Conejo Valley Unified. Because the pocket straddles the city line and sits near boundary edges, confirm the assignment with the district for the specific home.
Is Rolling Oaks a good fit for me?
It fits buyers who want acreage, horses, privacy and the freedom to build without an HOA, and who are comfortable with county rules, fire zone insurance and septic or well on some lots. It is not for anyone who wants a turnkey tract home, sidewalks or a quick resale market.
Thinking about Rolling 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 HOA registry (GIS)
- Conejo Valley Unified School District schools
- CAL FIRE Fire Hazard Severity Zone maps
- Conejo Open Space Conservation Agency trails
- Conejo Open Space Foundation history
- ABC7 on new CAL FIRE hazard maps in Ventura County
- Niche profile of Conejo Academy
- The Lakes at Thousand Oaks
- Hoodline on new tenants at The Lakes
Facts checked October 2026.
