Rolling Hills Homes with HOA

Welcome to Rolling Hills, California – a hidden gem nestled in the heart of Los Angeles County, where the rolling landscapes and luxurious lifestyles come together to create an idyllic community. Known for its stunning views and serene atmosphere, Rolling Hills is an exclusive enclave that offers residents a unique blend of natural beauty and modern amenities.

As you explore this picturesque city, you’ll find homes that are not just residences, but masterpieces. The properties here are often set on sprawling lots, showcasing breathtaking vistas of the surrounding hills and valleys. With a strong emphasis on privacy and security, many homes are part of a Homeowners Association (HOA), ensuring that the community remains well-maintained and harmonious. The HOA provides residents with access to exclusive amenities, including beautifully landscaped parks, walking trails, and recreational facilities, all while fostering a sense of camaraderie among neighbors.

Rolling Hills is not only about stunning homes; it’s also about lifestyle. The city boasts a wealth of outdoor activities, from horseback riding to hiking, allowing residents to immerse themselves in the natural beauty that surrounds them. The community is conveniently located near top-rated schools, shopping centers, and dining options, making it an ideal place for families and professionals alike.

Experience the charm and tranquility of Rolling Hills, where every day feels like a retreat. Whether you’re looking for a luxurious estate or a cozy family home, this enchanting city offers a lifestyle that is truly unparalleled. Come and discover the magic of Rolling Hills – your dream home awaits!

Newest Rolling Hills Homes with HOA

$7,995,000

5 Beds ⋅ 6 Baths ⋅ SB26206322 MLS ⋅ Coming Soon Status

Welcome to 28 Caballeros Rd — a rare offering in the gated hillside enclave of Rolling Hills, where sprawling parcels, hiking and horse trails, and lush greenery set the stage for true resort-style living above the clouds. This exceptional 5,874 sq ft estate (4,727 sq ft main house plus a ~1,147 sq ft guest house) offers 5 bedrooms and 5.75 baths, fully reimagined by Kim Lapin Interiors and Canyon Homes in a modern Montecito Ranch aesthetic. Enter through a private courtyard with a running fountain into a home defined by vaulted ceilings and thoughtful flow throughout. Curated natural, vintage, and hand-crafted finishes are found at every turn — Calacatta Viola marble, solid white oak and walnut cabinetry with unlacquered brass and polished nickel hardware, zellige and sand-cast brick, warm hardwood floors, and four fireplaces. A formal living room opens directly to the stunning backyard, with views of the Queen's Necklace and twinkling city lights setting the tone for indoor-outdoor living. The North side of the home holds the kitchen, dining, and family living room — a warm, easy space built for lazy days together. The chef's kitchen features double ovens and a sunny breakfast nook, opening naturally into the family room beyond. The South side offers four bedrooms, each with its own ensuite bath for maximum privacy. The primary suite is a true sanctuary, with soaring vaulted ceilings and natural light pouring in, its own fireplace, a walk-in closet, and a spa-like primary bath designed for a quiet retreat. Downstairs, a bonus den awaits with a projector screen, bar area, and direct access outside, along with a laundry room and additional office space. The existing ADU — which includes the 5th bedroom, bath, and kitchenette with sweeping views — was expanded by 500 sq ft. The result is a fully built-out gym with white oak floors, mirrored walls, and minimal-frame Titoni sliding doors opening to views of the horse corral. Outside, enjoy a fenced yard with pool, spa, fire pit, and BBQ area, plus full horse facilities and direct access to the Purple Canyon trail — a true equestrian and entertainer's dream in one of the South Bay's most coveted communities.

28 Caballeros Road, Rolling Hills

$4,200,000

4 Beds ⋅ 4 Baths ⋅ PV26199644 MLS ⋅ Active Status

A beautifully appointed ranch-styled home nestled amid a lush, landscaped setting in the heart of Rolling Hills. Surrounded by manicured grounds, mature trees and winding pathways through the vineyard you get a great sense of tranquility and rustic charm. The elegantly designed home creates a great sense of comfort and features beautiful pastoral and ocean views. The floor plan design provides a living room centered around an open hearth stone fireplace, a large family room with a wet bar accented with high soaring ceilings, a lower level area that is ideal for a media room, game room and entertainment. The updated kitchen is designed for the creative chef with a wolf range and stainless steel appliances. The 4 bedrooms and office are highlighted with a luxurious primary suite with a resort styled bathroom and walk-in closet. The balance of the bedrooms have a jack and jill set up and an ensuite guest bedroom. The exterior grounds create a special outdoor environment with a PV stone patio with pool and spa overlooking the views and a built in outdoor kitchen and parklike yard area. The original barn structure could be a workshop, gardening shed or studio. Located within a private gated community, the home offers a serene setting with coastal breezes and quiet outdoor spaces.

6 Caballeros, Rolling Hills

$4,850,000

4 Beds ⋅ 7 Baths ⋅ PV26190866 MLS ⋅ Active Status

Nestled within the prestigious gated sanctuary of Rolling Hills, this exceptional Sedona style estate combines equestrian elegance with modern sophistication on an expansive, 1.3-acre all-usable lot. Spanning 5,022 square feet of thoughtfully designed living space, the four-bedroom, seven-bathroom residence is anchored by imported antique French Oak floors and soaring open ceilings throughout the main living areas that evoke a grand, airy feel. At the heart of the home, a large open kitchen invites effortless entertaining, seamlessly connecting guests to a spacious layout featuring a dramatic double-sided fireplace shared between the formal living and family room. An integrated Alexa/Lutron system offers smart control over lighting and audio with easy potential for expansion. The primary suite serves as a private sanctuary, boasting a recently remodeled, spa-inspired bathroom and two generous walk-in closets. Outside, resort-style grounds highlight a sparkling pool and spa alongside a fully equipped outdoor kitchen with a built-in BBQ and sink. Exceptional equestrian facilities include a three-stall barn with a tack room and an expansive riding arena, complemented by a cozy detached living quarters complete with its own fireplace—perfect for guests, staff, or dual-living. Uniquely versatile, the equestrian grounds offer endless potential to easily transform into a sprawling play area or creative space to suit any lifestyle.

21 Eastfield, Rolling Hills

$4,800,000

5 Beds ⋅ 4 Baths ⋅ PV26174009 MLS ⋅ Active Status

Nestled on a tranquil cul-de-sac in the exclusive 24/7 guard-gated enclave of Rolling Hills, this contemporary ranch-style masterpiece boasts unprecedented levels of luxury, space, and views of the ocean, Queen’s Necklace, Malibu coastline, nearby canyon, inspiring mountains, and sparkling city lights, including downtown Los Angeles, SoFi Stadium, and the iconic Hollywood sign. This single level residence surrounded by lush, manicured landscape was originally built in 1964 but taken down to the studs and rebuilt in 2020. The reimagined home boasts towering cathedral ceilings lined with skylights and high quality custom cabinetry, millwork, tile, and hardwood flooring throughout. It is also fitted with new plumbing, dual zone HVAC, energy efficient dual pane windows & sliding doors, electrical systems and roof. Step inside to discover a home lovingly designed to maximize beauty, ambiance, and light. The great room, which includes living, dining, and a towering library wall with rolling ladder, boasts a stunning wall of glass showcasing the breathtaking views. The open-concept kitchen sets the stage for your most daring culinary and entertainment adventures, featuring vaulted ceilings, quartz counters, chef-grade appliances, a huge central island, custom cabinetry as well as a walk-in pantry & wine fridge/bar counter nearby. The spacious primary suite showcases the best view and offers double walk-in closets and a beautiful spa-like bathroom. Meanwhile, there is one bedroom en-suite and one bedroom with direct access to the adjacent hallway bathroom. Two additional bedrooms share another hallway bathroom that exudes luxury and comfort. Outside, the entertainment space is surrounded by rose gardens, with multiple tiers of dining, sunning, and seating patios cascading down the backyard. The highlight is the 30' infinity-edge pool and spa finished with white marble, blue glass pebble bottom tiles & 4 waterfalls. It is complemented by an adjacent lounging area and a seating area with fireplace, perfect for relaxation and entertainment while overlooking the stunning views. This house has a 3-car garage with lots of space for storage, while a circular, paver driveway presents a grand entrance and plenty of guest parking. With direct access to hundreds of acres of horse trails and equestrian zoning, the property offers a lifetime of luxury living. This is a rare opportunity to make this dream home yours.

2 El Concho Lane, Rolling Hills

$3,300,000

4 Beds ⋅ 2 Baths ⋅ PV26152805 MLS ⋅ Active Status

An incredibly rare opportunity to acquire a ready-to-build 1.4-acre property with approved plans in place. Currently there is an existing 2,490 sq. ft. residence, though the true value lies in the land, plans and vision for the future estate. With nearly four years of meticulous planning, design, engineering, and governmental review already completed, this property offers a rare opportunity to bypass the most time-intensive stages of development. This exceptional offering allows the next owner to move directly into the next chapter and create a one-of-a-kind Rolling Hills luxury retreat. The approved plans call for a stunning mid-century modern ranch estate designed by renowned architect Luis de Moraes that captures gorgeous Palos Verdes coastline, ocean, and Catalina Island views. Envisioned at approximately 4,870 sq. ft. of living space, plus a 967 sq. ft. oversized 3-car garage, the future residence features 5 bedrooms, 5.5 bathrooms, a spacious great room, laundry room, wine cellar, and a thoughtfully designed primary suite with dual walk-in closets and a beautiful en-suite bathroom. The outdoor living experience is equally impressive, with plans for a true backyard oasis complete with an expansive pool deck, covered porch, outdoor kitchen, waterfall-edge pool and spa, and firepit designed for effortless entertaining against a breathtaking coastal backdrop with Catalina views. A rare chance to bypass years of planning and bring an extraordinary Rolling Hills estate vision to life. Set within one of Southern California’s most private and coveted gated cities Rolling Hills offers a lifestyle defined by space, privacy, equestrian tradition, and natural beauty. With just under 700 homes across approximately three square miles, all properties are set on at least one acre and surrounded by the community’s signature rural character. Residents enjoy three staffed gated entrances, nearly 30 miles of recognized bridle trails, resident riding rings, tennis facilities, and breathtaking views that span the coastline, ocean, city lights and pastoral canyons. Buyer to verify all plans and approvals. Approved plans and Geological reports are available upon‌‌‌‌‌‌‌‌‌‌‌‌‌ request.

4 Spur Lane, Rolling Hills

$19,500,000

6 Beds ⋅ 7 Baths ⋅ PV26145356 MLS ⋅ Active Status

Welcome to the Nike House, where unrivaled architecture, privacy, opportunity, and absolute serenity meet at the top of Palos Verdes in the private, gated city of Rolling Hills. As the only true Modern Ranch Estate on the entire Peninsula, this six-bedroom, seven-bathroom trophy property stands as an architectural gem. It was designed by award-winning and visionary architect Robert L. Thompson, the mastermind behind over 70 structures on the Nike Campus. The residence proudly displays dramatic lines, spectacular backlighting, soaring ceilings, and intentional design elements never before seen in this exclusive community.Thoughtfully curated to inspire both productivity and restoration, the estate seamlessly blends executive-caliber workspaces with world-class amenities—including a magnificent office suite overlooking a tranquil Asian garden, two additional private offices, a cozy screening room, a professional gym with a custom sauna, and an expansive outdoor kitchen overlooking the resort-style pool and spa—embodying the very best of Southern California indoor-outdoor living. A true rarity in Palos Verdes, this exquisite property spans nearly four acres of fully usable land, where panoramic Pacific Ocean and Catalina views meet the sparkling city lights of Los Angeles. The sprawling grounds also feature a stunning poolside guest residence complete with two bedrooms, a full bathroom, and a spacious living area. Acres of gardens begin with a picturesque olive tree alley, leading to an expansive orchard featuring a multitude of citrus, avocado, and exotic fruits, a colorful rose garden with a storybook playhouse, and well-manicured flower gardens and lush green lawns. Plenty of open, flat space remains for a barn, corrals, and/or a tennis court. This is a once-in-a-lifetime opportunity where extraordinary living can become your everyday experience.

18 E Crest Road, Rolling Hills

$3,950,000

4 Beds ⋅ 6 Baths ⋅ PV26128743 MLS ⋅ Active Status

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. The expansive great room showcases soaring wood-beamed ceilings, beautiful oak flooring, and a dramatic stacked-stone fireplace, opening seamlessly to the gourmet kitchen appointed with Viking and Sub-Zero appliances and an impressive 10-foot island. An oversized multipurpose room functions beautifully as a second family room or game room and offers flexibility as a potential additional bedroom. Outdoors, unwind by the resort-style pool with Baja shelf and spa, complemented by a convenient pool house with bathroom, shower, and dressing area. A secluded approximately 800 sq. ft. Guest House features one bedroom and bath, a living room with fireplace, kitchenette, and sweeping countryside views, which is ideal for guests, extended stays or the perfect home office. Equestrian amenities include a three-stall barn with tack room and hot walker, with easy access to miles of riding trails and the nearby riding ring. An oversized stamped-concrete driveway provides effortless access to the three-car garage. Additional highlights include air conditioning, backup generators, collapsible doors, four fireplaces, and the rare, tranquil feeling of country living just moments from everything the Peninsula has to offer.

3 Poppy Trail, Rolling Hills

$3,650,000

4 Beds ⋅ 4 Baths ⋅ PV26107296 MLS ⋅ Active Status

Perched at the heart of the prestigious 24-hour guard-gated city of Rolling Hills, this stunning single-level residence offers a rare sanctuary where breathtaking views, serene natural beauty, and refined luxury converge. The iconic Queen's Necklace coastline, shimmering city lights, and a tranquil tree-lined canyon unfold before you, creating a living backdrop that is nothing short of extraordinary. A landscaped walkway leads to a secluded double-door entry, where open-beam cathedral ceilings, polished travertine tile floors, and abundant natural light set an immediate tone of quiet sophistication. Expansive picture windows and sliding glass doors wrap the entire home, dissolving the boundary between indoors and out, and drawing the serene gardens, patios, and sweeping vistas seamlessly into every room. The open living area flows gracefully from a formal living room and dining space to a casual dining area. Additionally, a large family room is nearby with its own fireplace for everyday enjoyment. A double-sided fireplace connects the living room to a versatile bonus room, ideal as an office, gym or tearoom. The chef's kitchen is appointed with granite countertops, a breakfast bar, custom cabinetry, premium appliances, and a wine fridge. Every detail speaks to both culinary function and gracious entertaining. The private bedroom wing is a world apart. The primary suite is a true sanctuary, featuring a generous sitting area, a spacious walk-in closet and two additional closets. Meanwhile, the primary bathroom has a dual sink vanity, soaking tub, and shower. Two additional bedrooms are of good size, both with a walk-in closet and share a Jack-and-Jill bathroom. A privately located 4th bedroom en-suite offers flexibility as a guest/in-law retreat, while a powder room and laundry room complete the thoughtful floor plan. Outside, the grounds unfold into a lush, multi-tiered outdoor retreat. 4 gentle water fountains in separate garden courtyards fill the air with a soothing calm. A sparkling pool and spa face the open horizon with a sitting and lounging area, while a private wood deck offers the perfect perch for quiet reflection or meditation as the sun rises or the city lights begin to twinkle. A barn with two stables adds rare future potential to this already remarkable estate. To live in Rolling Hills is to live apart from the ordinary. Ensconced in privacy, surrounded by nature, and elevated above it all. This is a rare offer that defines a life well-lived.

14 Georgeff, Rolling Hills

$2,000,000

SB26088969 MLS ⋅ Active Status

In a rare and extraordinary offering, 16 and 14 Johns Canyon Road are available simultaneously, presenting a once-in-a-lifetime opportunity to acquire two adjoining properties on a peaceful cul-de-sac within the guard-gated equestrian city of Rolling Hills. 16 Johns Canyon Road offers a truly remarkable expanse of land itself, defined by breadth, privacy, and natural beauty. Tucked among towering eucalyptus and mature shade trees, the property unfolds into serene, park-like grounds with an openness that is both inviting and inspiring. The approach reveals a gently elevated site with generous usable grounds spanning over 2 acres. At the heart of the property, the sweeping long lawn is anchored by a charming gazebo, long utilized as a setting for celebrations, special events, and clandestine gatherings. This central space provides both presence and flexibility, equally suited for tranquil enjoyment or larger-scale entertaining. Palos Verdes stone pathways, paired with well-established landscaping, create a sense of place that feels grounded, natural, and timeless. The grounds extend beyond the main lawn to additional open areas, including an established orchard and further stretches of land. Mature greenery, flowering elements, and layered plantings create a landscape rich in texture and character, providing an incredible foundation for future vision and expansion. The scale of the parcel allows for a variety of uses, including a custom residence, equestrian facilities, gardens, recreational spaces, or a thoughtfully designed estate compound. Positioned within one of the South Bay’s most exclusive communities, the property benefits from convenient access to the Crest Gate with a guard near Crenshaw Boulevard, while maintaining a strong sense of seclusion. Independently compelling, 16 Johns Canyon Road is further distinguished by its simultaneous availability with the adjacent 14 Johns Canyon Road—featuring a historic residence, equestrian improvements, and a one-of-a-kind entertainment structure—creating a once-in-a-lifetime chance to establish a larger estate. Opportunities to acquire side-by-side properties of this scale and character within Rolling Hills are exceptionally limited. Whether envisioning a private retreat, equestrian estate, or long-term legacy holding, 16 Johns Canyon Road offers a canvas where vision can take shape—defined by space, privacy, and enduring potential within one of the most coveted and protected settings in Los Angeles County.

16 Johns Canyon Road, Rolling Hills

$3,200,000

5 Beds ⋅ 5 Baths ⋅ SB26088047 MLS ⋅ Active Status

Set within the private, guard-gated equestrian city of Rolling Hills, an extraordinary offering unfolds across two adjoining properties on a private cul-de-sac—14 and 16 Johns Canyon Road—now available simultaneously for a once-in-a-lifetime chance to create a combined estate of exceptional scale and potential. 14 Johns Canyon Road presents a legacy property rooted in the historic Rancho Elastico. Originally constructed in 1926 as a ranch bunkhouse and thoughtfully expanded over time, the residence has evolved into a substantial multi-wing home centered around an open courtyard, blending original character with later additions, for a highly flexible floorplan. The formal entry with powder room opens to a spacious living room with soaring wood-beam ceilings, a Palos Verdes stone fireplace, and French doors to a patio. The formal dining room is well connected to the kitchen, featuring a center island, pantry, and breakfast nook with access to the courtyard for indoor-outdoor living. An open hall with an adjoining study leads to the original portion of the home, where a library, additional living area, second kitchen, bedroom, full bathroom, and office nook provide space for a variety of uses. The home continues with a wing including two bedrooms, a shared bath, and nearby laundry room. A spacious primary suite features a five-piece bath and cedar-lined closets. A large basement with interior and exterior access is well-suited for a gym, studio, or workshop. The grounds reflect a rich equestrian and lifestyle heritage, with multiple horse stalls and runs, expansive lawns, mature shade trees, and a variety of gardens and open spaces. Outdoor features include multiple gathering areas, BBQ patios, an enclosed yard with playhouse, freestanding writing retreat, and areas previously used for animal care and rehabilitation, contributing to the property’s unique and meaningful history. The showstopper is a converted concrete barn, reimagined as a two-level saloon and entertainment venue. Complete with a stage, lighting and sound systems, bar, balcony, and restroom, it offers a truly one-of-a-kind setting for private events, performances, or creative pursuits. The driveway continues to the adjacent parcel at 16 Johns Canyon Road, also available. Together, these two properties create a rare opportunity to establish a private compound or legacy estate—where history, space, privacy, and vision converge in one of the South Bay’s most exclusive and distinctive communities.

14 Johns Canyon Road, Rolling Hills

$6,000,000

5 Beds ⋅ 6 Baths ⋅ WS26065821 MLS ⋅ Active Status

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. The backyard features a cascading waterfall from the house to the negative edge pool and in-ground spa sits next to a large high vaulted ceilings and gourmet chef's kitchen with separate formal dining area. The master suite features its own fireplace with a large walk-in closet, private mahogany wood adorned study w/fireplace, and a spa-quality master bath.

60 Crest Road E, Rolling Hills

$5,950,000

6 Beds ⋅ 7 Baths ⋅ PV26057607 MLS ⋅ Active Status

Set within the prestigious, guard-gated city of Rolling Hills, this extraordinary 5,500-square-foot residence offers sweeping City and Queen’s Necklace views from its bedrooms, decks and patios. French doors seamlessly blend indoor and outdoor living throughout this mostly single-story gem. Upon entry, the foyer welcomes with soaring ceilings and reveals an expansive, light-filled living room. A semi-open concept kitchen with Thermador appliances, granite countertops, and light wooden cabinetry serves as the perfect setting for both everyday living and the special moments in between. Vaulted ceilings, recessed lighting, curated alabaster light fixtures, hardwood floors, wide hallways, and generously sized bathrooms create an airy environment that feels both elegant and inviting. The oversized basement features a fitness room, storage room, full bathroom and wet bar, French doors openi to a Large Mediterranean style patio complete with an outdoor fireplace—offering additional space to retreat- or entertain! The home is comprised of 6 bedrooms and 7 bathrooms, including a fully self-contained guest house. Outdoors, a sparkling pool, putting green, barn, lush landscaping, and panoramic views provide an exceptional setting for both relaxed living and unforgettable entertaining. Welcome Home!

49 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.