27366 Winding Way, Malibu, CA 90265
Property image
Property image
OFF MARKET

$8,156,300

Trulia Estimate
as of Sep 15, 2026
  • 1 Bed
  • 1 Bath
  • 632 sqft

27366 Winding Way, Malibu, CA 90265

Home Highlights

Single-Family Home
632 sqft
$12,906/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 27366 Winding Way.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Private 1 bedroom, 1 bathroom Malibu guest house located on a quiet and peaceful property near the scenic Escondido Canyon trails. This beautifully renovated unit features a modern kitchen with stainless steel appliances and an updated bathroom, creating a comfortable and stylish living space.

Surrounded by Malibu's natural beauty, the property offers a tranquil environment ideal for those seeking privacy and relaxation. Enjoy easy access to hiking trails, Malibu beaches, Pacific Coast Highway, dining, and shopping.

Utilities included, electricity, gas, water, and internet.

Utilities included: electricity, gas, water, and internet paid by owner.
Maximum lease term: 12 months.
No smoking permitted inside or outside the property.
Maximum of two vehicles permitted. No boats, trailers, RVs, or oversized vehicles allowed on premises at any time.
This is a shared-lot property with the owner's primary residence located on premises. Tenant must maintain a quiet-use environment at all times. No on-site trades work, use of power tools, mechanical equipment, or hobby and craft activities that generate noise or vibration are permitted inside or outside the unit including the garage at any hour.
Garage is for vehicle parking and personal storage only. Use as a workshop, workstation, or for any trades or hobby work is strictly prohibited.
Pets welcome with landlord approval only. Limit two pets. Pet rent: $150 $300/month per pet depending on size. Tenant responsible for all pet-related damages.
Minimum gross monthly income of 3x the monthly rent required. Proof of income documentation required prior to lease signing.
A completed Zillow application including credit and background screening is required prior to scheduling a tour. Application approval is for touring purposes only and does not constitute a rental offer, lease agreement, or guarantee of tenancy. Additional financial documentation and final landlord approval are required before any lease is executed.
Tenant is responsible for maintaining the property in good condition throughout the lease term.
27366 Winding Way, Malibu, CA 90265 is a 1 bedroom, 1 bathroom, 632 sqft single-family home. It last sold for $6,935,000 on Jun 7, 2024 (149,040% above the $4,650 asking price). More recently, it was listed as a rental in April 2026 with an asking price of $4,750 per month. That rental listing was removed on June 15, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $8,156,300.

Home Details for 27366 Winding Way

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 27366 Winding Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
27860 Winding Way, Malibu, CA
0.53
Single-Family Home
$7,650,000
06/05/26
4
4.5
4,733 sqft
27071 Sea Vista Dr, Malibu, CA
0.55
Single-Family Home
$2,975,000
11/14/25
4
2.5
2,197 sqft
27218 Pacific Coast Hwy, Malibu, CA
0.46
Single-Family Home
$17,600,000
10/14/25
3
3.5
3,325 sqft
27403 Pacific Coast Hwy, Malibu, CA
0.24
Single-Family Home
$11,200,000
10/31/25
7
9
8,744 sqft
27368 Escondido Beach Rd, Malibu, CA
0.38
Single-Family Home
$11,650,000
10/10/25
5
5.5
6,640 sqft
27950 Winding Way, Malibu, CA
0.66
Single-Family Home
$3,200,000
12/22/25
4
3
2,641 sqft
6158 Ramirez Canyon Rd, Malibu, CA
0.88
Single-Family Home
$3,400,000
09/23/25
3
2.5
3,040 sqft
28036 Sea Lane Dr, Malibu, CA
0.76
Single-Family Home
$8,250,000
11/05/25
3
4.5
4,159 sqft
6138 Ramirez Canyon Rd, Malibu, CA
0.90
Single-Family Home
$5,150,000
06/09/26
4
3.5
3,800 sqft
26616 Ocean View Dr, Malibu, CA
1.27
Single-Family Home
$1,320,000
08/24/26
2
2
830 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Malibu

Last updated Mar 2026
Average rent
$20K
$2KMoM
Available listings
335
View rental market trends in Malibu, CA

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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jun 15, 2026
Source: Zillow Rentals
ListingRemoved
$4,650
May 7, 2026
Source: Zillow Rentals
PriceChange
$4,650
Price decreased by 2%
Apr 28, 2026
Source: Zillow Rentals
Listed For Rent
$4,750
Apr 8, 2026
Source: Zillow Rentals
ListingRemoved
$4,850
Mar 13, 2026
Source: Zillow Rentals
Listed For Rent
$4,850

Frequently asked questions about 27366 Winding Way

  • What is 27366 Winding Way estimated to be worth?
    Trulia's estimated value for 27366 Winding Way in Malibu, CA is $8,156,300.
  • What is the price history for 27366 Winding Way?
    27366 Winding Way in Malibu, CA last sold for $6,935,000 in June 2024.
  • Is Malibu a buyer's or seller's market?
    Malibu is currently a balanced market, based on recent for-sale activity.
  • 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 recently sold homes in Malibu, CA.
  • Does 27366 Winding Way have air conditioning?
    Yes, 27366 Winding Way in Malibu, CA has air conditioning.
  • Does 27366 Winding Way have laundry facilities?
    Yes, 27366 Winding Way in Malibu, CA has in-unit laundry.

Homes for rent near 27366 Winding Way

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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