27445 Winding Way, Malibu, CA 90265
Property image
Property image
FOR SALE
2.03 ACRES

$11,450,000

  • 6 Beds
  • 7.5 Baths
  • 6,837 sqft (on 2.03 acres)

27445 Winding Way, Malibu, CA 90265

Est. Mortgage $71,784/mo*
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Home Highlights

Single-Family Home
Built in 2002
2.03 acre lot
$1,675/sqft
Garage

Local Information

  • Map ViewExplore the area around 27445 Winding Way.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 7 hours ago
Listing courtesy of Christopher Cortazzo DRE # 01190363, (310) 579-5887
Compass, (310) 230-5744
Source: CLAW, MLS#26865021
Also Listed on bridgeMLS/CCAR/Bay East AOR, CRMLS.

Home Details for 27445 Winding Way

Interior Features

Interior Details
Number of Rooms: 2Types of Rooms: Bathroom, Kitchen
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 8Number of Bathrooms (full): 7Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6837 Square Feet
Appliances & Utilities
Appliances: Built-Ins, Microwave, Range Hood, Range, Oven, Freezer, Disposal, Exhaust Fan, Dishwasher, Dryer, Refrigerator, Range/Oven, Washer, Barbeque, Water Heater UnitDishwasherDisposalDryerLaundry: Laundry Room,InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central Air,Zoned,Air ConditioningHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 3Fireplace: Living Room, Family RoomSpa: Private, Heated, In Ground, Tub With JetsHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: BlindsDoor: French Doors, Sliding DoorsFlooring: Stone Tile, WoodCommon Walls: Detached/No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoEntry Location: FoyerAccessibility: NoneFloors: Stone Tile, Wood
View
Has a ViewView: City Lights, Coastline, Catalina, Mountain(s), Ocean, Pool, Rocks, Bluff, White Water, Tree Top, Panoramic
Security
Security: Gated Community, Automatic Gate, Prewired, Gated, Alarm System

Exterior Features

Exterior Home Features
Patio / Porch: Rock/Stone, PatioFencing: Gate, FencedOther Structures: CabanaExterior: Balcony, Barbecue, Living Room BalconyHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 10No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 12Parking: Driveway,Garage Door Opener,Garage - 2 Car,Covered,Open,Private Garage,Guest
Pool
Pool: In Ground, Pool Cover, PrivatePool
Frontage
Waterfront: NoneRoad Frontage: Private RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 46

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Residential, Single Family ResidenceStructure Type: DetachedArchitecture: Detached
Building
Building: High Ceilings (9 Feet+), Sprinkler SystemNot Attached PropertyNo Additional Parcels
Property Information
Parcel Number: 4460005001

Price & Status

Price
List Price: $11,450,000Price Per Sqft: $1,675

Active Status

MLS Status: Active

Location

Direction & Address
City: Malibu
School Information
Elementary School District: Santa Monica-Malibu Unified School DistrictJr High / Middle School District: Santa Monica-Malibu Unified School DistrictHigh School District: Santa Monica-Malibu Unified School District

Agent Information

Listing Agent
Listing ID: 26865021

Building

Building Area
Building Area: 6837 Square Feet

HOA

No HOA

Lot Information

Lot Area: 2.0317 Acres

Listing Info

Special Conditions: Standard

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 26865021Water ViewWater View: Coastline, Catalina, Ocean, White Water

Additional Information

HOA Amenities: Gated

Around this home

What Locals Say about Malibu

At least 89 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 87 % Say it's dog friendly

  • 73 % Say yards are well-kept

  • 73 % Say there's wildlife

  • 70 % Say people would walk alone at night

  • 67 % Say it's quiet

  • 63 % Say parking is easy

  • 62 % Say they plan to stay for at least 5 years

  • 59 % Say there's holiday spirit

  • 50 % Say neighbors are friendly

  • 45 % Say kids play outside

  • 43 % Say it's walkable to grocery stores

  • 38 % Say it's walkable to restaurants

  • 36 % Say there are sidewalks

  • 35 % Say there are community events

  • 19 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • John Clark Gable - Debra Gable
    "Beautiful neighborhood. Very dog friendly. Morning View Drive is one of the most popular areas in Malibu because of the beach and school system. "
    0
    Flag
  • Nancy Solorio
    "Many people walk there dogs here. Many great hiking trails to take them on. Dogs should be kept on a leash for their safety with cars and wildlife. "
    0
    Flag
  • Jennifer Connell
    "Everyone has dogs and some kind of small yard. We also have lots of dog walkers. The mornings are great when they all wake up and say good morning to each other. "
    0
    Flag
  • Ann Doneen
    "Friday night car and music fests in a grocery parking lot, an annual Labor Day chili cook off, a Chumash Day, and when old surfers and important environ my mentalist people die, the surfers have a paddle out. Memorial for them."
    0
    Flag
  • Trulia User
    "Family oriented low key place. Not a party scene and feels very quiet. Friendly people and good mix. "
    2
    Flag
  • Ruth Q.
    "This community is top notch. Very well kept and security is high quality 24/7. Perfect weather and location, too!"
    3
    Flag
  • Nancy S.
    "There are many great dog park and neighborhoods to walk in. The difficulty is that dogs are not allowed on the beaches. "
    9
    Flag
  • Magdalena
    "Very quiet and comfortable. Animal friendly. Not so open to the public which we love. We enjoy living here. Very peaceful."
    1
    Flag
  • Didier C.
    "No events at all where I live. It’s a highway with multiple theft and robberies........................"
    0
    Flag
  • Didier C.
    "Don’t live on PCH. Dangerous and lots of theft. Stay in the hills. ..................................."
    0
    Flag
  • Cheriedh9
    "There is almost no public transportation, buses, taxi’s, Lyft, Uber etc:( There have been many times I haven’t been able to get a ride when I couldn’t drive. "
    0
    Flag
  • Michael L.
    "None- Malibu is becoming too rich for its own good. It used to be fun but now it’s cheesy and full of self important gits "
    0
    Flag
  • Bliss T.
    "Do not commute - I am now retired Commuting is a nightmare in the AM as it is always bumper to bumper It would make a huge improvement if they would sink the lights or open the center lane southbound and facilitate the traffic flow. If it rains you can guarantee that the storm drains haven’t been cleared as they have never been on a maintenance schedule in the past forty years I have lived here so they always backup and cause the highway to have huge flooded area resulting in some clown going to fast and causing an accident. The first rains always seem to cause the signal lights to go out too! People seem to forget that PCH is one of the year long most heavily used highways in the country. The first rains always mix with the motor oil on the road making it VERY DANGEROUS yet people forget to slow down thus more accidents than normal. Summertime brings thousands of tourists so forget trying to go in to town. If a weekend is nice weather you can guarantee it’s bumper to bumper coming into Malibu in the AM and even worse from 3 PM on going back to town. If CAL trans does any work they always set up before their allocated 8:30 AM time causing more “looky-loo” slowing !"
    0
    Flag
  • Bliss T.
    "I have lived on this beach in different locations for over 30 years. When you walk on the beach the people are always friendly and say hello. "
    0
    Flag
  • Heather B.
    "Three miles to the bus stop and closest shopping area I.e. market, bank. 20 minutes to get to any affordable super market. PCH is impacted often. "
    0
    Flag
  • Alexis S.
    "There are many families in Malibu and it is a community oriented town. Kids will most often be seen playing at the beach or parks, there are not a lot of neighborhoods with cul de sacs. However, many families enjoy outdoor activities year round."
    0
    Flag
  • Alexis S.
    "very supportive community, chili cook off, beach/surfing, family, dog friendly, animal friendly, liberal attitude."
    0
    Flag
  • Jasminaber
    "It is by the ocean surfers writes it ya always s summer here etc people are nice young and old and diverse green environmentalists artist and renewable ... it has university with students and faculty from all over the world ... many art venues theaters and cultural centers museums and galleries ... "
    0
    Flag
  • Octaviolun
    "This place is the perfect retreat from a busy city day life. Almost no noise and the sky and views makes it worth every commute. "
    0
    Flag
  • Temmalibu
    "Feels safe and open. Love being near the ocean. Weather is great although wish we had more rain. The downside is the number of tourists as they cause heavy traffic since we basically have one road"
    0
    Flag
  • Nataliasg1
    "Respectful and quiet family. Beautiful Energie. We love to be the best neighbors. Get to know our people around in case of any emergency. "
    0
    Flag
  • T J.
    "I own a home in Malibu and work nearby. Great place to raise kids. A cosmopolitan small town. Much untrammeled nature. Very relaxed."
    1
    Flag
  • Margaret H.
    "Close to Zuma Beach, Starbucks, Stores etc. Trancas Park at end of street."
    7
    Flag

Market trends in Malibu

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
282
8MoM

Home Value

Trulia Estimate
$10.6M
Since last month
Decreased$675K (-6%)
Since last year
Increased$2M (+23.2%)
Since last sale
Increased$3M (+34.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +155% in the last 10 years
MonthEstimated value
2026
August 2026$10.65M
August 2026$10.63M
July 2026$11.33M
June 2026$9.63M
May 2026$9.34M
April 2026$9.06M
March 2026$9.06M
February 2026$8.96M
January 2026$8.84M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27403 Pacific Coast Hwy, Malibu, CA
0.52
Single-Family Home
$11,200,000
10/31/25
7
9
8,744
27860 Winding Way, Malibu, CA
0.40
Single-Family Home
$7,650,000
06/05/26
4
4.5
4,733
6420 Delaplane Rd, Malibu, CA
0.53
Single-Family Home
$14,500,000
05/19/26
5
5.5
7,600
27832 Pacific Coast Hwy, Malibu, CA
0.51
Single-Family Home
$55,000,000
07/29/26
6
7.5
8,775
27910 Pacific Coast Hwy, Malibu, CA
0.55
Single-Family Home
$35,000,000
05/22/26
4
7
5,154
26799 Sea Vista Dr, Malibu, CA
1.13
Single-Family Home
$6,800,000
05/08/26
7
9
6,678
28177 Rey De Copas Ln, Malibu, CA
0.88
Single-Family Home
$4,900,000
10/15/25
4
6
6,823
6138 Ramirez Canyon Rd, Malibu, CA
0.67
Single-Family Home
$5,150,000
06/09/26
4
3.5
3,800

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
27311 Winding Way, Malibu, CA 90265
0.12
$7,833,600
7
7.5
6,445
Off Market
27547 Pacific Coast Hwy, Malibu, CA 90265
0.26
$14,463,400
6
7
6,969
Off Market
27555 Pacific Coast Hwy, Malibu, CA 90265
0.29
$1,950,000
-
-
-
For Sale
Address Not Disclosed, Malibu, CA 90265
0.34
$15,200,000
6
7.5
7,940
For Sale
27727 Pacific Coast Hwy, Malibu, CA 90265
0.31
$6,495,000
4
4
3,908
For Sale
27553 Pacific Coast Hwy, Malibu, CA 90265
0.31
$5,995,000
4
4.5
3,699
For Sale
6245 Murphy Way, Malibu, CA 90265
0.36
$8,647,200
6
5
5,928
Off Market
27715 Pacific Coast Hwy, Malibu, CA 90265
0.32
$48,000,000
6
7
11,000
For Sale
6093 Murphy Way, Malibu, CA 90265
0.38
$14,495,000
7
8
10,500
For Sale
27860 Winding Way, Malibu, CA 90265
0.40
$7,650,000
4
4.5
4,733
Recently Sold
22445-22455 Pacific Coast Hwy, Malibu, CA 90265
0.42
$8,067,000
13
13
7,890
Off Market

Price and Tax history

DateEventPrice
Jul 27, 2026
Source: CLAW #26865021
Listed For Sale
$11,450,000
Jan 16, 2026
Source: CLAW #25-485867
ListingRemoved
$50,000
Jan 19, 2025
Source: CLAW #25-485867
Listed For Rent
$50,000
Jan 16, 2025
Source: CLAW #24-348343
ListingRemoved
$48,500
May 7, 2024
Source: CLAW #24-348343
PriceChange
$48,500
Price decreased by 19%

LGBTQ Local Legal Protections

Christopher Cortazzo, Compass, (310) 230-5744
Agent Phone: (310) 579-5887
© 2026 The MLS™ - Combined L.A. Westside MLS (CLAW). All rights reserved. Based on information from The MLS™ - Combined L.A. Westside MLS (CLAW as of 2026-09-11 23:23:29 PDT. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Some IDX listings have been excluded from this website.

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Frequently asked questions about 27445 Winding Way

  • What is the estimated monthly payment for 27445 Winding Way?
    Based on a $11,450,000 list price with 20% down at today's rates, the estimated monthly payment for 27445 Winding Way in Malibu, CA is approximately $72,713 (about $61,379 principal & interest, $11,259 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Malibu?
    Residents describe Malibu, CA as dog-friendly, well-kept, and quiet. Most residents say you need a car. See homes for sale in Malibu, CA.
  • What are the closest schools to 27445 Winding Way?
    The closest schools to 27445 Winding Way in Malibu, CA are Malibu High School (rated 8/10), Malibu Middle (rated 7/10), Webster Elementary School (rated 10/10).
  • What is 27445 Winding Way estimated to be worth?
    Trulia's estimated value for 27445 Winding Way in Malibu, CA is $10,634,900.
  • Does 27445 Winding Way have air conditioning?
    Yes, 27445 Winding Way in Malibu, CA has air conditioning.
  • Does 27445 Winding Way have a pool?
    Yes, 27445 Winding Way in Malibu, CA has a pool.
27445 Winding Way, Malibu, CA 90265 is a 6 bedroom, 8 bathroom, 6,837 sqft single-family home built in 2002. This property is currently available for sale and was listed by CLAW on Jul 27, 2026. The MLS # for this home is MLS# 26865021.