Rolling Hills (166) Homes with Two Levels Stories

Welcome to Rolling Hills, an enchanting enclave nestled in the heart of Los Angeles County, California. This picturesque community is renowned for its serene landscapes, equestrian trails, and stunning views that offer a perfect blend of luxury and tranquility. With its rolling hills and expansive green spaces, this area provides a peaceful retreat from the hustle and bustle of city life, making it an ideal place for families and individuals seeking a serene lifestyle.

One of the most appealing aspects of Rolling Hills is its exquisite homes, many of which feature two-level stories that embody both elegance and functionality. These multi-story residences are designed to maximize space and comfort, providing ample room for family gatherings, entertaining guests, or simply enjoying the breathtaking views from your own private balcony. The architectural styles in Rolling Hills range from modern masterpieces to charming Mediterranean estates, each exuding a unique character that complements the natural beauty of the surroundings.

Living in Rolling Hills means embracing a lifestyle filled with outdoor activities, from horseback riding along scenic trails to hiking in the nearby parks. The community is also conveniently located near top-rated schools, shopping centers, and fine dining options, ensuring that residents have everything they need within reach.

Whether you’re looking for a luxurious family home or a tranquil retreat, Rolling Hills offers an exceptional living experience that combines elegance, comfort, and a sense of community. Come discover the charm of this remarkable region and find your dream home among the rolling hills today!

Newest Rolling Hills (166) Homes with Two Levels Stories

$3,500,000

5 Beds ⋅ 5 Baths ⋅ SB26088047 MLS ⋅ Active Status

Set within the private, guard-gated equestrian city of Rolling Hills, an extraordinary offering unfolds across two adjoining properties on a private cul-de-sac—14 and 16 Johns Canyon Road—now available simultaneously for a once-in-a-lifetime chance to create a combined estate of exceptional scale and potential. 14 Johns Canyon Road presents a legacy property rooted in the historic Rancho Elastico. Originally constructed in 1926 as a ranch bunkhouse and thoughtfully expanded over time, the residence has evolved into a substantial multi-wing home centered around an open courtyard, blending original character with later additions, for a highly flexible floorplan. The formal entry with powder room opens to a spacious living room with soaring wood-beam ceilings, a Palos Verdes stone fireplace, and French doors to a patio. The formal dining room is well connected to the kitchen, featuring a center island, pantry, and breakfast nook with access to the courtyard for indoor-outdoor living. An open hall with an adjoining study leads to the original portion of the home, where a library, additional living area, second kitchen, bedroom, full bathroom, and office nook provide space for a variety of uses. The home continues with a wing including two bedrooms, a shared bath, and nearby laundry room. A spacious primary suite features a five-piece bath and cedar-lined closets. A large basement with interior and exterior access is well-suited for a gym, studio, or workshop. The grounds reflect a rich equestrian and lifestyle heritage, with multiple horse stalls and runs, expansive lawns, mature shade trees, and a variety of gardens and open spaces. Outdoor features include multiple gathering areas, BBQ patios, an enclosed yard with playhouse, freestanding writing retreat, and areas previously used for animal care and rehabilitation, contributing to the property’s unique and meaningful history. The showstopper is a converted concrete barn, reimagined as a two-level saloon and entertainment venue. Complete with a stage, lighting and sound systems, bar, balcony, and restroom, it offers a truly one-of-a-kind setting for private events, performances, or creative pursuits. The driveway continues to the adjacent parcel at 16 Johns Canyon Road, also available. Together, these two properties create a rare opportunity to establish a private compound or legacy estate—where history, space, privacy, and vision converge in one of the South Bay’s most exclusive and distinctive communities.

14 Johns Canyon Road, Rolling Hills

$6,250,000

6 Beds ⋅ 7 Baths ⋅ PV26057607 MLS ⋅ Active Status

Set within the prestigious, guard-gated city of Rolling Hills, this extraordinary 5,500-square-foot residence offers sweeping City and Queen’s Necklace views from its bedrooms, decks and patios. French doors seamlessly blend indoor and outdoor living throughout this mostly single-story gem. Upon entry, the foyer welcomes with soaring ceilings and reveals an expansive, light-filled living room. A semi-open concept kitchen with Thermador appliances, granite countertops, and light wooden cabinetry serves as the perfect setting for both everyday living and the special moments in between. Vaulted ceilings, recessed lighting, curated alabaster light fixtures, hardwood floors, wide hallways, and generously sized bathrooms create an airy environment that feels both elegant and inviting. The oversized basement features a fitness room, storage room, full bathroom and wet bar, French doors openi to a Large Mediterranean style patio complete with an outdoor fireplace—offering additional space to retreat- or entertain! The home is comprised of 6 bedrooms and 7 bathrooms, including a fully self-contained guest house. Outdoors, a sparkling pool, putting green, barn, lush landscaping, and panoramic views provide an exceptional setting for both relaxed living and unforgettable entertaining. Welcome Home!

49 Saddleback, Rolling Hills

$19,800,000

5 Beds ⋅ 11 Baths ⋅ PV26046180 MLS ⋅ Active Status

38 Saddleback in Rolling Hills is an architectural triumph, a 9,400-square-foot Contemporary Ranch nestled on a sprawling 54,732-square-foot lot. Designed by Criss Gunderson with inspiration from Cliff May, the estate’s positioning was guided by two Feng Shui masters to ensure a perfect harmony with its environment. This intentionality is matched by an uncompromising commitment to natural materials, featuring Italian Limestone floors, handmade oak and walnut doors with Rocky Mountain hardware, and the same Hope steel doors found at the Getty Museum. The home offers a dual-kitchen experience designed by Cooper Pacific of Beverly Hills: a sleek contemporary kitchen equipped with Gaggenau and Miele appliances and a "Entertainment Kitchen" featuring a handmade La Cornue stove, a Wood Stone pizza oven, and 150-year-old reclaimed barn beams. For the entertainer, the dining room is anchored by a Lindsey Adelman chandelier, while the lower level reveals a Cinema de Cuore theater with custom Fortress seating and a wine cellar constructed from recycled French castle stones and wine-barrel wood. The residence functions as a private sanctuary, offering five bedrooms and nine bathrooms outfitted with elite fixtures from Gessi, Graff, and Axor. The primary suite is a masterclass in luxury, boasting pure white marble walls and Calacata floors. Wellness is central to the design, with a comprehensive spa including an all-cedar dry sauna, steam room with rain shower, massage room, and a soaking tub that transitions to an outdoor shower. Modern convenience is integrated through a laundry chute, a dumbwaiter, and a dedicated library/office located in a separate barn to preserve the sanctity of family life. Outside, the property captures 270-degree panoramic views stretching from Malibu through Los Angeles all the way to Long Beach Harbor, creating an organic flow between the high-design interiors and the breathtaking landscape. This is a home built with conviction, prioritizing craftsmanship, history, and the simple joy of a life well-lived.

38 Saddleback, Rolling Hills

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Based on information from California Regional Multiple Listing Service, Inc. as of . This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.