Rolling Hills Homes with Paddle Tennis Association amenities

Welcome to Rolling Hills, California – a hidden gem nestled in the picturesque hills of Los Angeles County. Known for its serene landscapes and luxurious lifestyle, Rolling Hills offers a unique blend of natural beauty and modern convenience. This exclusive community is characterized by its sprawling estates, lush greenery, and breathtaking views of the Pacific Ocean and the surrounding mountains.

One of the standout features of Rolling Hills is its commitment to an active and engaging lifestyle, particularly for those who enjoy paddle tennis. The community boasts a dedicated Paddle Tennis Association, providing residents with access to top-notch facilities and a vibrant social scene. Whether you’re a seasoned player or a beginner looking to pick up a new hobby, the association fosters a welcoming environment where neighbors can connect, compete, and enjoy the game together.

Homes in Rolling Hills are not just residences; they are sanctuaries designed for comfort and luxury. Many properties come equipped with expansive outdoor spaces, perfect for entertaining or simply unwinding after a long day. The blend of upscale living and community-centered activities makes Rolling Hills an ideal place for families and individuals alike.

With its proximity to Los Angeles, residents can enjoy the best of both worlds – the tranquility of suburban life and the excitement of city amenities. From top-rated schools to scenic parks and equestrian trails, Rolling Hills truly offers a lifestyle that caters to every need. Discover the charm of Rolling Hills and find your dream home in this enchanting community today!

Newest Rolling Hills Homes with Paddle Tennis Association amenities

$6,795,000

5 Beds ⋅ 5 Baths ⋅ PV26127741 MLS

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

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 CRISNet MLS as of All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed.