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Welcome to 28 Caballeros Rd "” a rare offering in the gated hillside enclave of Rolling Hills, where sprawling parcels, hiking and horse trails, and lush greenery set the stage for true resort-style living above the clouds. This exceptional 5,874 sq ft estate (4,727 sq ft main house plus a ~1,147 sq ft guest house) offers 5 bedrooms and 5.75 baths, fully reimagined by Kim Lapin Interiors and Canyon Homes in a modern Montecito Ranch aesthetic. Enter through a private courtyard with a running fountain into a home defined by vaulted ceilings and thoughtful flow throughout. Curated natural, vintage, and hand-crafted finishes are found at every turn "” Calacatta Viola marble, solid white oak and walnut cabinetry with unlacquered brass and polished nickel hardware, zellige and sand-cast brick, warm hardwood floors, and four fireplaces. A formal living room opens directly to the stunning backyard, with views of the Queen's Necklace and twinkling city lights setting the tone for indoor-outdoor living. The North side of the home holds the kitchen, dining, and family living room "” a warm, easy space built for lazy days together. The chef's kitchen features double ovens and a sunny breakfast nook, opening naturally into the family room beyond. The South side offers four bedrooms, each with its own ensuite bath for maximum privacy. The primary suite is a true sanctuary, with soaring vaulted ceilings and natural light pouring in, its own fireplace, a walk-in closet, and a spa-like primary bath designed for a quiet retreat. Downstairs, a bonus den awaits with a projector screen, bar area, and direct access outside, along with a laundry room and additional office space. The existing ADU "” which includes the 5th bedroom, bath, and kitchenette with sweeping views "” was expanded by 500 sq ft. The result is a fully built-out gym with white oak floors, mirrored walls, and minimal-frame Titoni sliding doors opening to views of the horse corral. Outside, enjoy a fenced yard with pool, spa, fire pit, and BBQ area, plus full horse facilities and direct access to the Purple Canyon trail "” a true equestrian and entertainer's dream in one of the South Bay's most coveted communities.
Property Type(s):
Single Family
| Last Updated | 9/26/2026 | Year Built | 1981 |
|---|---|---|---|
| Community | 166 - Rolling Hills | Garage Spaces | 3.0 |
| County | Los Angeles |
Additional Details
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Double Oven, Dryer, Ice Maker, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Heater |
| AREA | 166 - Rolling Hills |
| BARN/EQUESTRIAN | Yes |
| BASEMENT | Finished, Yes |
| CONSTRUCTION | Stucco |
| EXTERIOR | Barbecue |
| FIREPLACE | Yes |
| GARAGE | Attached Garage, Yes |
| HEAT | Central |
| HOA DUES | 16789|Annually |
| INTERIOR | Built-in Features, High Ceilings, Master Downstairs, Pantry, Walk-In Closet(s) |
| LOT | 1.3937 acre(s) |
| LOT DESCRIPTION | Back Yard, Cul-De-Sac, Landscaped, Sloped Down |
| LOT DIMENSIONS | 60,709 |
| PARKING | Attached, Direct Access, Driveway, Garage |
| POOL | Yes |
| POOL DESCRIPTION | Private, In Ground |
| SEWER | Unknown |
| STORIES | 1 |
| STYLE | Ranch, Spanish |
| UTILITIES | Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | City Lights |
| WATER | Public |
Location
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Listed with Compass
The information being provided by Conejo Simi Moorpark Association of REALTORS® (“CSMAR”) is for the visitor's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. Any information relating to a property referenced on this web site comes from the Internet Data Exchange (“IDX”) program of CSMAR. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. Any information relating to a property, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The data contained herein is copyrighted by CSMAR and is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited.
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