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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

    23 Caballeros Road, Rolling Hills, California 90274

    32Picture(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

    2950 Palos Verdes Drive, Rolling Hills, California 90274

    7Picture(s)
    1.17Sqft
    Investor’s Dream in Rolling Hills – Rare Fixer-Upper with High Upside Potential. Unlock the hidden value of this prime real estate opportunity in the prestigious City of Rolling Hills. Set on a sprawling lot of 1.16 acres along tree lined Palos Verdes Drive North, this single-level property is brimming with potential and ready for transformation.
    $1,700,000

    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

    44Picture(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, on a sprawling 2.4 acres of pristine land. A extensive renovation completed in 2024 showcases meticulous craftsmanship and top-tier finishes throughout.
    $3,650,000

    Residential For Sale

    2 Eucalyptus Lane, Rolling Hills, California 90274

    75Picture(s)
    1.59Sqft
    This secluded estate is located in the prestigious guard gated community of Rolling Hills. Enjoy the elegance of this more than 5,100 square foot well planned home which divided into living area, entertainment area and business area. Living area with 5 bedrooms plus 3 full bathroom and center courtyard. Center courtyard can be used as outdoor dining, pool table, or table tennis area.
    $5,300,000

    Residential For Sale

    50 Eastfield Drive, Rolling Hills, California 90274

    76Picture(s)
    1.69Sqft
    Modern Ranch Home Built in 1999 by the current owners from the ground up. This home has all of the space and amenities anyone could want! With privacy and views of the Harbor Breakwater and Ocean, Long Beach City Lights and Coastline to the south, one will see glorious sunrises. With 1.
    $6,000,000

    Residential For Sale

    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.
    $3,995,000
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