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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

    38 Saddleback, Rolling Hills, California 90274

    59Picture(s)
    1.26Sqft
    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.
    $19,800,000

    Residential For Sale

    3 Poppy Trail, Rolling Hills, California 90274

    27Picture(s)
    2.77Sqft
    Set on approximately 2.7 acres in the exclusive, gated community of Rolling Hills, this exceptional equestrian estate blends refined living with the serenity of the countryside. Beautifully renovated in 2023, the approximately 3,833 sq. ft. main residence offers 3 bedrooms and 3.5 bathrooms.
    $4,500,000

    Residential Sold

    9 Middleridge Lane, Rolling Hills, California 90274

    37Picture(s)
    1.27Sqft
    Prime location! This classic Rolling Hills ranch home is conveniently located on a quiet leafy street.
    $3,675,000

    Residential For Sale

    15 Caballeros, Rolling Hills, California 90274

    70Picture(s)
    1.29Sqft
    Set within the prestigious gated community of Rolling Hills, this home presents a contemporary style combining refined luxury, exceptional quality and breathtaking panoramic views from the Santa Monica Bay to the LA Basin. The captivating views serve to highlight this exceptional property both day and night.
    $6,500,000

    Residential For Sale

    1 Outrider Road, Rolling Hills, California 90274

    1Picture(s)
    1.14Sqft
    F
    $4,200,000

    Residential For Sale

    2 Eucalyptus Lane, Rolling Hills, California 90274

    60Picture(s)
    1.59Sqft
    The Polo House - A single-level architectural estate on ~1.6 acres inside the south gates of Rolling Hills. The Polo House is a newly elevated single-level estate set on a rare ~1.6-acre street-to-street parcel inside the south gates of Rolling Hills.
    $5,300,000

    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

    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 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

    2 Chuckwagon Road, Rolling Hills, California 90274

    81Picture(s)
    1.17Sqft
    Now is your chance to live Behind the Gates, as we say On the Hill. Calling gardeners, artists & avant-garde visionaries. Amazing value within a private city on over an acre... Designed for the eco-conscious buyer with an eye for innovation. This home is not just a place to live—it’s a statement of values.
    $2,495,000
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