For Sale

Listed by Christopher Cortazzo from Compass

Source: Combined LA Westside Multiple Listing Service, Inc #26865021

27445 Winding Way, Malibu, CA, 90265

$11,450,000

6
8
12
6837 sq. ft.
88499 sq. ft.

SingleFam

30+ days on the market

What's around 27445 Winding Way

About this property

With sweeping views from nearly every room, soaring ceilings, walls of glass, and exquisite architectural detailing throughout, this exceptionally private contemporary estate offers the ideal setting for both grand-scale entertaining and peaceful retreat. Set behind gates on more than two acres at the end of a cul-de-sac, the property is surrounded by beautifully terraced and landscaped grounds featuring expansive lawns, flagstone pathways, pomegranate, guava, grapefruit, and orange trees, as well as scenic vista points.The home's refined contemporary interior preserves timeless architectural details, including graceful arched openings and a dramatic double-height foyer anchored by an elegant curved staircase with scrolled railings leading to a columned mezzanine on the upper level. The living and dining room is framed by expansive windows showcasing panoramic views of verdant hillsides, Little Dume, the coastline, the Pacific Ocean, and Catalina Island, while glass doors open to a spacious view terrace ideal for al fresco dining and entertaining. The updated chef's kitchen features a tray ceiling, granite-topped center island, walk-in pantry, breakfast area with wraparound views, and a breakfast bar overlooking the inviting sunroom and family room with a fireplace and automated window coverings. A media room and two guest bedrooms complete the main level. Upstairs, four en suite bedrooms each enjoy private balconies, including the exceptional primary suite with a sitting room, meditation room or office, fireplace, private balcony, dual walk-in closets, dual spa-inspired bathrooms, and breathtaking ocean views. Additional highlights include three fireplaces, a newly resurfaced ocean-view pool and spa, expansive lawns, multiple outdoor patios, a four-car garage, parking for approximately ten additional vehicles in the motor court, and numerous smart home features.

Looking for more information on 27445 Winding Way?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties for sale nearby

For Sale
$10,849,000
7015 Grasswood Ave
Malibu CA 90265
6
7
10
Single-Family
Listing courtesy of Plus Real Estate Group
For Sale
$48,000,000
27715 Pacific Coast Highway
Malibu CA 90265
6
8
15
Single-Family
Listing courtesy of Compass
For Sale
$39,500,000
33360 Pacific Coast Hwy
Malibu CA 90265
6
6
3
Single-Family
Listing courtesy of W Real Estate

Other properties for sale by Compass

For Sale
$4,000,000
6259 Frondosa Dr
Malibu CA 90265
4
5
4
Single-Family
Listing courtesy of Compass
For Sale
$2,400,000
7006 Birdview Avenue
Malibu CA 90265
Land
Listing courtesy of Compass
For Sale
$1,825,000
4567 Via Mariano
Thousand Oaks CA 91320
4
4
3
Single-Family
Listing courtesy of Compass

Browse properties sold in nearby areas

The multiple listings information is provided by The MLS/CLAW from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 The MLS/CLAW. All Rights Reserved. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent