27445 Winding Way, Malibu, CA 90265
OFF MARKET

27445 Winding Way
Malibu, CA 90265

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

$9,347,100

Trulia Estimate
as of Jun 13, 2026
Est. Refi. Payment $55,746/mo*
Refinance Your Home

$9,347,100

Trulia Estimate
as of Jun 13, 2026
Est. Refi. Payment $55,746/mo*
Refinance Your Home
6 Beds
8 Baths
6,837 sqft
(on 2.03 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This single-family home is located at 27445 Winding Way, Malibu, CA. 27445 Winding Way is in Malibu, CA and in ZIP code 90265. This property has 6 bedrooms, 8 bathrooms and approximately 6,837 sqft of floor space. This property has a lot size of 2.03 acres and was built in 2002.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 27445 Winding Way

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: CentralHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, HardwoodGated Entry
Interior Details
Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Office, PantryCeiling Fan
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Property Information

Year Built
Year Built: 2002Year Updated: 2002
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Rental Terms, Policies & Fees

Furnished

Exterior Features

Exterior Home Features
Exterior: StuccoPatio
Pool
Pool
Parking & Garage
Parking Spaces: 12Parking: Off Street

Community

Units in Building: 1

Lot Information

Lot Area: 2.03 acres

Price History for 27445 Winding Way

DatePriceEventSource
01/16/2026$50,000ListingRemovedCLAW #25-485867
01/19/2025$50,000Listed For RentCLAW #25-485867
01/16/2025$48,500ListingRemovedCLAW #24-348343
05/07/2024$48,500PriceChange
CLAW #24-348343
01/17/2024$60,000Listed For RentCLAW #24-348343
12/19/2023ListingRemovedCLAW #23-235535
03/10/2023$60,000Listed For RentCLAW #23-235535
03/10/2023ListingRemovedZillow Rentals #23-235535
01/25/2023$60,000Listed For RentZillow Rentals #23-235535
11/08/2022ListingRemovedZillow Rental Manager
07/25/2022$60,000PriceChange
Zillow Rental Network_1 #22-149395
04/26/2022$57,000Listed For RentZillow Rental Manager
04/05/2022$7,900,000Sold
N/A
03/08/2022$8,450,000PendingCLAW #20-625210
02/22/2022$8,450,000ContingentCLAW #20-625210
08/18/2021$8,450,000Listed For SaleCLAW #20625210
01/28/2021$8,450,000ListingRemovedLocal MLS #20625210
11/18/2020$8,450,000PriceChange
Agent Provided
07/09/2019$8,995,000PriceChange
Agent Provided
02/22/2019$9,995,000Listed For SaleAgent Provided
10/13/2018$24,995ListingRemovedAgent Provided
08/31/2018$24,995Listed For RentAgent Provided
10/05/1999$925,000Sold
N/A
11/07/1997$530,000Sold
N/A

Market trends in Malibu

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
270
13MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$103,464
Assessment$8,383,542
Home facts updated by county records

Homeowner tools

Estimated monthly rent$32,727/mo
List your home for rent

Homes for rent near 27445 Winding Way

See what comparable homes in the neighborhood are renting for.
Skip to last item
Skip to first item

Comparable Sales for 27445 Winding Way

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
0.39
Single-Family Home
$7,650,000
06/05/26
4
4.5
4,733
6420 Delaplane Rd, Malibu, CA
0.52
Single-Family Home
$14,500,000
05/19/26
5
5.5
7,600
27910 Pacific Coast Hwy, Malibu, CA
0.54
Single-Family Home
$35,000,000
05/22/26
4
7
5,154
28036 Sea Lane Dr, Malibu, CA
0.65
Single-Family Home
$8,250,000
11/05/25
5
5.5
4,159
26799 Sea Vista Dr, Malibu, CA
1.14
Single-Family Home
$6,800,000
05/08/26
7
9
6,678
26799 Pacific Coast Hwy, Malibu, CA
1.16
Single-Family Home
$6,800,000
05/19/26
7
8
6,400
28177 Rey De Copas Ln, Malibu, CA
0.87
Single-Family Home
$4,900,000
10/15/25
4
6
6,823
6138 Ramirez Canyon Rd, Malibu, CA
0.65
Single-Family Home
$5,150,000
06/09/26
4
3.5
3,800
28882 Via Venezia, Malibu, CA
1.24
Single-Family Home
$6,395,000
01/26/26
5
6.5
6,273

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 27445 Winding Way.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Malibu

At least 88 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

  • 36 % Say there are community events

  • 18 % 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Garage

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Explore by feature - Outdoor Space

Homes for sale near 27445 Winding Way

Skip to last item
Skip to first item

Off Market Homes Near 27445 Winding Way

Skip to last item
Skip to first item
27445 Winding Way, Malibu, CA 90265 is a 6 bedroom, 8 bathroom, 6,837 sqft single-family home built in 2002. This property is not currently available for sale. 27445 Winding Way was last sold on Apr 5, 2022 for $7,900,000. The current Trulia Estimate for 27445 Winding Way is $9,347,100.