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.
Bedrooms
5
Bathrooms
5
Square Feet
5,000
Lot Size
85,956 sqft
Year Built
1963
Property Type
Single Family Residence
Days on Market
1
HOA Fee
$7700/mo
Garage Total
2
MLS #
PV26127741
Interior Features
Breakfast Bar, Eat In Kitchen, In Law Floorplan, Recessed Lighting, All Bedrooms Down, Bedroom On Main Level, Main Level Primary, Primary Suite
Fireplace
Living Room
Appliances
Disposal
Laundry
Laundry Room
Main Level Bedrooms
5
Main Level Bathrooms
5
Cooling
See Remarks
Heating
Central
Total Parking Spaces
2
Garage Spaces
2
Attached Garage
Yes
Parking Features
Driveway Level, Garage
Patio & Porch
Patio
Security
Gated With Guard, Gated Community, Gated With Attendant, Twenty Four Hour Security
Lot Features
Two To Five Units Acre, Back Yard, Cul De Sac, Front Yard, Horse Property, Lot Over40000 Sqft, Landscaped, Yard
Pool Features
Private
Sewer
Septic Tank
Water Source
Public
Controlled Access, Horse Trails, Picnic Area, Paddle Tennis, Pickleball, Guard, Security, Tennis Courts, Trails
Horse Trails, Gated
$0
| Rating | School Name | ||
|---|---|---|---|
| No school data available for this area. | |||
Balanced market
Avg. time on market
This is a Balanced Market. Homes are selling at a moderate pace.
Flood Risk
Minimal — not in a FEMA flood zone
Wildfire Risk
Moderate — near wildland-urban interface
Heat Risk
Low — moderate summer temperatures
Earthquake Risk
Southern California seismic zone
Based on price, location, and features
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