3249 Bennett Dr

Step into the magic of this fully gated and private 1920s Hollywood Hills Spanish compound — a storybook retreat where vintage charm meets modern comfort. From the moment you arrive, you’re surrounded by lush greenery, inviting outdoor spaces, and sweeping mountain and treetop views that instantly set the tone for relaxed California living. This 4+4 offers 3235sf with a main house, a casita and an additional 756sf flex space making alomst 4000sf of usable space. Inside, classic architectural details blend beautifully with updated finishes, including rich tile and hardwood floors, smooth stucco walls, and sun-drenched rooms framed by oversized picture windows that fill the home with natural light all day long.

The main level is made for entertaining and easy everyday living, featuring a chef’s kitchen alongside formal living, dining, and family rooms — perfect for hosting intimate dinners, lively gatherings, or cozy nights in. On the 2nd level, you’ll find three bedrooms, including your inviting primary suite complete with a cedar closet, private deck for morning coffee or sunset unwinding, and a spa-inspired bath with a deep soaking tub.

The lower level transforms into your creative playground offering an incredible flex space ideal for recording studio, a private movie lounge, or the ultimate work-from-home setup. Adding to the versatility is a charming one-bedroom casita with its own living area, kitchenette, and private entrance — perfect for guests, extended stays, or a turnkey rental opportunity.

Outside is where the fun truly continues: unwind in the custom hot tub beneath the stars, gather around tranquil fountains, dine al fresco on multiple terraces, or lounge on the many decks while catching the iconic Hollywood Hills breeze. The street-to-street lot offers two convenient entrances, plus the rare luxury of a four-car garage.

All of this is ideally tucked just moments from beloved restaurants, boutique shopping, scenic hiking trails, the Hollywood Bowl and major studios — giving you peaceful hillside living with the pulse of the city close at hand.