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    One of the most exclusive neighborhoods on the Palos Verdes Peninsula is the City of Rolling Hills. ‘Behind the gates,’ as local vernacular would have it, this private and secluded area is patrolled by three 24-Hour guarded gates for the strictly residential-only properties. Furthermore, for an added level of comfort and security, one may only access the city by permit and guests must be authorized by a resident for entrance.

    Located on top of the lovely hills of the Palos Verdes Peninsula, Rolling Hills residents enjoy fantastic views facing north, east, and south with gorgeous city lights and often Pacific Ocean vistas from this highest point of the peninsula. Rolling Hills properties are all situated on at least one acre, but some estates can be much larger, even up to seven-plus acres. Also, each property is an equestrian property, and therefore requires a devoted area for a barn. The city also includes 23 miles of private riding trails which are maintained through the Rolling Hills Community Association which also provides private guards, road maintenance, two riding rings and three tennis courts, as well as an LA County Fire Station on Crest Road. All of these comforts and services do come with a price, typically twenty cents per $100 of the sale price of the property.

    Architecturally, homes here are required to be in the ranch style, painted white, and one level. Inhabitants achieve multi-level living via going underground. When working with the slope of the hills this can be achieved without feeling ‘underground’ or as if one is living in a basement. Meanwhile, there are some original 1930’s homes built in the colonial style along Williamsburg Lane.

    Bordering each property is the required white three-rail fences, and like other areas of the Peninsula, there are no streetlights or sidewalks along the private roads. Homes range in price from about $1,500,000 to about $8,500,000. There are some exceptional properties in the marketplace with one asking for up to $40,000,000 (although it has never sold). All in all, Rolling Hills is an upscale equestrian neighborhood with exquisite homes and meticulously cared for grounds, roads and horse trails.

    While there are no commercial properties for entertainment within the gates, the locals with membership are in close proximity to the Rolling Hills Country Club that includes a golf course, tennis facilities, and both formal and casual dining options.

    Children here attend nearby Rancho Vista Elementary, Dapplegray Elementary, Miraleste Intermediate, Palos Verdes High School or Palos Verdes Peninsula High School for the exceptional public schools. For private schools, nearby Chadwick serving K-12 students, Rolling Hills Country Day School for K-8, or Rolling Hills Prep for 6-12 in San Pedro is close at hand. With the privacy and security Rolling Hills has to offer potential buyers, this beautiful upscale neighborhood is unique to itself on the Palos Verdes Hill.

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    Residential For Sale

    45 Crest Road, Rolling Hills, California 90274

    40Picture(s)
    2.02Sqft
    Behind the exclusive gated community of Rolling Hills lies a property of rare distinction—an expansive private sanctuary offering over two lush acres with commanding, unobstructed 180-degree views that stretch from Malibu’s coastline to the twinkling lights of Long Beach.
    $5,500,000

    Residential Sold

    42 Saddleback Road, Rolling Hills, California 90274

    1Picture(s)
    2.41Sqft
    *
    $3,900,000

    Residential For Sale

    5 Caballeros Road, Rolling Hills, California 90274

    45Picture(s)
    2.14Sqft
    Built in 1958, this single-level Mid- Century Ranch style home features 2 bedrooms, 3 baths, and a spacious family room with wet bar, spanning over 2,300 square feet poised perfectly on a 2.14-acre view lot. Tucked within LA's stunning Palos Verdes Peninsula, Rolling Hills is an exclusive gated rural enclave that perfectly balances privacy, natural beauty, and sophisticated living.
    $2,450,000

    Residential For Sale

    60 Crest Road, Rolling Hills, California 90274

    23Picture(s)
    3.17Sqft
    This beautiful single family residence is situated in a highly secured 24 hour guard gated city. This Contemporary classic ranch style with gorgeous views and large windows throughout. This Single story 5 bedrooms/6 bath estate sits on approx 3 acres of impeccable landscaping all behind a long and private gated driveway.
    $6,000,000

    Residential For Sale

    23 Caballeros Road, Rolling Hills, California 90274

    34Picture(s)
    1.11Sqft
    Nestled on 1.1 acres in the exclusive gated city of Rolling Hills, this beautifully appointed estate offers the perfect blend of timeless elegance with thoughtful modern upgrades all while overlooking serene views that stretch across the city. With approximately 3,800 sq. ft. of living space, the home features 4 bedrooms (2 currently used as offices), 3.
    $4,395,000

    Residential For Sale

    19 Caballeros Road, Rolling Hills, California 90274

    28Picture(s)
    1.17Sqft
    TRUST SALE - Unrivaled privacy and panoramic views converge in this exceptional single-story estate, located in the prestigious guard-gated community of Rolling Hills. Set on a private knoll, this 3,191 sq. ft. residence is a masterclass in serene luxury, with walls of glass framing sweeping vistas of glittering city lights and majestic mountains.
    $3,795,000

    Residential For Sale

    3 Poppy Trail, Rolling Hills, California 90274

    37Picture(s)
    2.77Sqft
    Nestled in a serene and private enclave between the canyons of the exclusive gate city of Rolling Hills, this extraordinary 2.7-acre equestrian estate offers a rare blend of luxury and nature. Completely renovated in 2023, the main residence spans approximately 3,833 sq. ft. and features 3 bedrooms and 3.5 bathrooms.
    $5,495,000

    Residential Sold

    14 Chuckwagon Road, Rolling Hills, California 90274

    54Picture(s)
    1.16Sqft
    Welcome to this exquisitely remodeled ranch-style sanctuary in the heart of Rolling Hills. Every inch of this exceptional estate has been thoughtfully curated—from the lush, manicured grounds to the luxurious finishes throughout—creating a one-of-a-kind, turnkey retreat. As you approach the home, you're greeted by a magical setting that feels like a world of its own.
    $3,899,000

    Residential For Sale

    13 Buggy Whip Drive, Rolling Hills, California 90274

    51Picture(s)
    1.97Sqft
    A Rare Cliff May-Designed Equestrian Estate with Unrivaled Views in Rolling Hills. Welcome to your private hilltop retreat, where classic California ranch architecture meets resort-style living. This spectacular 5-bedroom, 5.5-bath estate designed by iconic architect Cliff May is nestled behind the 24/7 guard-gated community of Rolling Hills.
    $7,000,000

    Residential For Sale

    2 Chuckwagon Road, Rolling Hills, California 90274

    79Picture(s)
    1.17Sqft
    A Fire-Resistant Passive Ranch Home within a Private City... Welcome to a visionary property that redefines sustainable luxury in this one-of-a-kind residence. It was the first home in California to use fire-resistant hempcrete, a non-toxic, carbon-negative material offering superior insulation, indoor air quality, and durability.
    $2,712,000

    Residential For Sale

    7 Cinchring Road, Rolling Hills, California 90274

    39Picture(s)
    1.02Sqft
    Imagine owning a piece of architectural history. Known as The Coe House, this exceptional Rolling Hills residence, designed by the legendary Richard Neutra, masterfully blends iconic mid-century modern design with refined contemporary updates. Thoughtfully restored, the home now features all the modern luxuries of today while preserving the classic design elements that define its timeless appeal.
    $4,150,000

    Residential For Sale

    2840 Palos Verdes Drive, Rolling Hills, California 90274

    5Picture(s)
    2.43Sqft
    Elevated luxury meets contemporary aesthetic in the prestigious City of Rolling Hills, this newly remodeled estate captures the sweeping unobstructed views of the glittering Los Angeles city lights. A extensive renovation completed in 2024 showcases meticulous craftsmanship and top-tier finishes throughout.
    $3,650,000
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