Rolling Hills (166) Homes with Paddle Tennis Association amenities

Welcome to Rolling Hills, a hidden gem nestled in the heart of Los Angeles County, California. This enchanting community is renowned for its breathtaking landscapes, lush greenery, and a lifestyle that seamlessly blends luxury with tranquility. Rolling Hills is a private, gated community that offers residents an unparalleled sense of security and exclusivity, making it a perfect retreat from the hustle and bustle of city life.

One of the standout features of Rolling Hills is its stunning homes, each uniquely designed to complement the natural beauty of the surroundings. Here, you’ll find spacious estates with sprawling gardens, panoramic views, and an abundance of outdoor space that invites relaxation and entertainment. Many properties come equipped with Paddle Tennis Association amenities, allowing residents to indulge in an active lifestyle right at their doorstep. Paddle tennis is not just a sport here; it’s a vibrant community activity that fosters connections among neighbors and friends.

In addition to the recreational opportunities, Rolling Hills boasts a rich array of equestrian trails, parks, and hiking paths, perfect for those who appreciate the outdoors. The area is also home to top-rated schools, making it an ideal choice for families seeking quality education for their children.

With its unique blend of luxury living, community spirit, and natural beauty, Rolling Hills stands out as a premier destination for those looking to call Los Angeles County home. Discover the charm of Rolling Hills today and experience a lifestyle that harmonizes elegance and leisure in one of California's most coveted neighborhoods.

Newest Rolling Hills (166) Homes with Paddle Tennis Association amenities

$6,795,000

5 Beds ⋅ 5 Baths ⋅ PV26127741 MLS ⋅ Active Status

A Legendary Cliff May Estate with Iconic Views and Endless Possibilities. Perched atop one of the most coveted streets in the exclusive guard-gated community of Rolling Hills, this extraordinary Cliff May-designed estate offers a rare opportunity to own one of the Peninsula's most remarkable properties. Set on approximately two usable acres, the residence captures breathtaking panoramic views stretching from the Queen’s Necklace and the Los Angeles skyline to dazzling city lights below. Originally selected by the former president of Southern California Edison as the premier homesite on Buggy Whip Drive, this exceptional property was chosen for its commanding 180-degree vistas, expansive flat grounds, and unparalleled privacy. Decades later, it remains one of Rolling Hills’ most treasured settings. The timeless California ranch architecture envisioned by renowned architect Cliff May seamlessly blends indoor and outdoor living. Nearly every room enjoys spectacular views, with walls of glass framing the skyline and filling the home with natural light. Vaulted ceilings, marble flooring, and elegant entertaining spaces create a refined yet comfortable environment. The thoughtfully designed floor plan features five bedrooms and five-and-one-half bathrooms, including formal living and dining rooms, a gourmet kitchen, and an adjoining family room that opens effortlessly to the outdoor entertaining areas. Outside, resort-style amenities await. A sparkling pool, expansive patios, and built-in barbecue create the ultimate setting for sunset entertaining. With approximately two flat acres, there is ample space for a pickleball court, tennis court, vineyard, orchard, or expanded equestrian facilities. Equestrian enthusiasts will appreciate the existing barn and corral with potential for future enhancement or possible conversion into an ADU or guest residence (buyer to verify with the City). A detached guest apartment with kitchenette provides comfortable accommodations for visitors, extended family, or live-in staff. Beyond the gates, Rolling Hills offers one of Southern California’s most coveted lifestyles with private riding and hiking trails, community tennis courts, three guarded entrances, and a serene rural atmosphere just minutes from beaches, shopping, dining, and award-winning schools.

13 Buggy Whip Drive, 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.