Only Half a Mile from the Beach, this $9,800,000 Masterpiece has all the Malibu Life has to Offer and More and is an Entertainer’s Dream

27366 Winding Way, Malibu, CA 90265

Listed by Madison Hildebrand & Jennifer Chrisman at Compass.


Property Photos Gallery

Photos provided by Madison Hildebrand & Jennifer Chrisman at Compass.

Property Description

Perched on 2.5 acres in the highly desirable Winding Way neighborhood, this architectural masterpiece is an entertainer’s dream. This expansive compound features remarkable ocean views, a heated pool and spa, an indoor racquetball court, a home theater, and a detached guest house – all while being located only minutes from the beach, hiking trails, schools and shopping. The gated driveway leads you from the cul-de-sac neighborhood, alongside the verdant landscaping to the front door of the main house – comprised of 5 bedrooms, 7.5 baths, two living areas, a chef’s kitchen, a home theater, and a sunken bank vault! Throughout the main residence you’ll find floor to ceiling windows, high ceilings, and striking coastline views. Detached from the main home are two other structures – a private racquetball court, and a guest home with its own kitchen and living room. The grounds are exquisite – complemented by flat grassy areas, a batting cage, vineyards, a wood-fire pizza oven and bbq area, a firepit, and built-in seating. Owner had plans to remodel which have been submitted to the City of Malibu. A buyer can pick up where the seller is leaving off or live in the house as-is. Only half a mile from the beach, this home has all the Malibu life has to offer and more!

Property Features

  • Bedrooms: 6
  • Full Bathrooms: 6
  • 3/4 bathrooms: 1
  • Half Bathrooms: 1
  • Living Area: 8,063 Sqft
  • Fireplaces: 3
  • Elevator: No
  • Lot Size: 2.57 Acres
  • Parking Spaces: 15
  • Garage Spaces: 5
  • Stories: 3
  • Year Built: 2001
  • Year Renovated: –

Property Price History

DateEventPricePrice/Sq FtSource
04/17/2023Listed$9,800,000$1,592TheMLSCLAW
01/02/2018Listing removed$6,950,000$862TheMLSCLAW
12/29/2017Sold$6,725,000$834TheMLSCLAW
05/04/2017Listed$6,950,000$862TheMLSCLAW
01/21/2017Listing removed$7,100,000TheMLSCLAW
10/31/2016Listed$7,100,000TheMLSCLAW
10/03/2014Sold$6,050,000$864TheMLSCLAW
09/25/2014Relisted$6,295,000$899TheMLSCLAW
08/28/2014Listing removed$6,295,000$899TheMLSCLAW
07/01/2014Price Changed$6,295,000$899TheMLSCLAW
06/05/2014Price Changed$6,495,000$928TheMLSCLAW
04/07/2014Listed$6,695,000$956TheMLSCLAW
10/10/2012Listing removed$25,000$4ITECH
09/27/2012Listing removed$6,850,000$1,113TheMLSCLAW
07/26/2012Listing removed$25,000$4TheMLSCLAW
07/25/2012Relisted$6,850,000$1,113TheMLSCLAW
07/24/2012Listing removed$6,850,000$1,113TheMLSCLAW
04/13/2012Listed for rent$25,000$4ITECH
04/13/2012Listed for rent$25,000$4TheMLSCLAW
04/11/2012Listed$6,850,000$1,113TheMLSCLAW
11/13/1997Sold$595,000$97Public Record
04/16/1993Sold$500,000$81Public Record
07/21/1989Sold$625,000$102Public Record

Property Reference

On Real Estate Platform

On Press, Media, Blog

  • Robb Report Real Estate
  • Luxury Houses
  • Global Mansion
  • Others: Architectural Digest | Dwell

Contact Madison Hildebrand, Phone: 310-818-5788 & Jennifer Chrisman, Phone: 310-818-5788 at Compass for more information. See the LISTING here.

Reminder: Above information of the property might be changed, updated, revised and it may not be on sale at the time you are reading this article. Please check current status of the property at links on Real Estate Platforms that are listed above.

Leave a Reply

Your email address will not be published. Required fields are marked *