NOT LISTED FOR SALE

27860 Winding Way Malibu, CA 90265

Malibu Area

Estimated Value: $7,583,294

4 Beds
4.5 Baths
4,733 Sq Ft
$1,602/Sq Ft Est. Value

Sale Details

Date Sold: June 5, 2026

Last sale price $7,650,000 $1,616 Per Sq Ft

Est. 1% decrease in value since last sale

Current estimated payment $48,098 / mo

67 Days on Market

Highlights

  • Ocean View
  • Detached Guest House
  • In Ground Pool
  • Webster Elementary School Rated A
  • 24-Hour Security
  • Gourmet Kitchen

About This Home

As of June 2026

Tucked behind mature hedging on one of Malibu's most desirable streets, this exquisite estate presents a striking blend of California modernism and rustic refinement. Completely reimagined with an emphasis on natural light, flow, and function, the property exudes a sense of serenity from the moment you arrive. Anchored by clean lines and framed by mature trees, the residence features a contemporary stucco exterior with sharp geometric rooflines and walls of glass that open to expansive grounds. Inside, the interiors unfold with organic warmth where wide-plank oak floors, beamed ceilings, vintage fixtures, and antique doors create a soulful counterbalance to the home's modern architecture. The heart of the home is a sunlit great room with soaring ceilings and disappearing walls of glass that open onto a lush green lawn and shimmering pool. Thoughtfully layered seating areas surround a central fireplace, while oversized iron chandeliers cast a warm glow overhead. The adjacent dining room framed by oversized sliders and a pair of reclaimed wood barn doors effortlessly connects to the gourmet kitchen. Designed for both utility and aesthetic impact, the kitchen features a massive center island with stone countertops, custom wood cabinetry, and open shelving, all illuminated by industrial pendant lighting. The primary suite is a haven of texture and tranquility, with a romantic canopy bed, hand-finished plaster walls, and direct access to the pool deck. A curated mix of woven textures, soft linens, and patinated wood imbue the space with an effortless global elegance. Beyond the main residence, the grounds unfold into a spectacular lifestyle setting. A sleek lap pool with integrated spa is flanked by sun loungers and bordered by lush privacy hedges. Tiered gardens bloom with vibrant plantings, and a thoughtfully designed dining terrace invites open-air meals beneath the trees. A fully realized edible garden, complete with raised beds and fruiting trees, enhances the property's sense of abundance and connection to nature. Nestled just beyond the garden, a beautifully finished guest house offers a peaceful retreat for visitors or an inspiring studio space. Featuring polished concrete floors, steel-framed glass doors, and warm natural textures throughout, the guest house evokes quiet luxury and lives like a private sanctuary perfect for work, creativity, or extended stays. Modern yet soulful, expansive yet intimate, this Winding Way estate offers a rare balance of architecture, landscape, and lifestyle just minutes from the beaches and boutiques of Malibu's eastern coastline.

Last Agent to Sell the Property

Chris Cortazzo

Compass License #01190363 Listed on: 02/27/2026

Compass

Last Buyer's Agent

Matthew Schwartz

Plus Real Estate License #02035608

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
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List Price
Sold Price
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Home Details

Home Type

  • Single Family

Year Built

  • Built in 1976

Lot Details

  • 1.06 Acre Lot
  • Gated Home
  • Landscaped
  • Secluded Lot
  • Sprinkler System
  • Lawn
  • Back and Front Yard
  • Property is zoned LCR11*

Property Views

  • Ocean
  • Panoramic
  • Mountain
  • Pool

Home Design

  • Contemporary Architecture
  • Turnkey

Interior Spaces

  • 4,733 Sq Ft Home
  • 2-Story Property
  • Open Floorplan
  • Built-In Features
  • Beamed Ceilings
  • High Ceiling
  • Recessed Lighting
  • Pendant Lighting
  • Gas Fireplace
  • Sliding Doors
  • Entryway
  • Living Room with Attached Deck
  • Dining Area
  • Home Office
  • Wood Flooring
  • Laundry Room

Kitchen

  • Gourmet Kitchen
  • Breakfast Bar
  • Double Oven
  • Range with Range Hood
  • Freezer
  • Dishwasher
  • Kitchen Island
  • Stone Countertops
  • Disposal

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Primary Bedroom Suite
  • Walk-In Closet
  • Powder Room
  • Double Vanity
  • Bathtub with Shower
  • Double Shower
  • Shower

Parking

  • 6 Car Garage
  • Private Parking
  • Driveway
  • Automatic Gate
  • Guest Parking
  • Uncovered Parking
  • Unassigned Parking

Pool

  • In Ground Pool
  • In Ground Spa

Outdoor Features

  • Balcony
  • Covered Patio or Porch
  • Outdoor Fireplace
  • Fire Pit
  • Outdoor Grill

Additional Homes

  • Detached Guest House

Location

  • Property is near public transit
  • City Lot

Utilities

  • Air Conditioning
  • Central Heating
  • Property is located within a water district

Community Details

  • No Home Owners Association
  • 24-Hour Security

Listing and Financial Details

  • Assessor Parcel Number 4460-006-012

Home Details

Home Type

Single Family

Year Built

Built in 1976

Lot Details

1.06 Acres

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Style: Contemporary
  • Levels: Two
  • Street Number Display: Yes
  • Entry Location: Foyer
  • Living Area: 4733
  • Lot Acreage: 1.0598
  • Stories: 2
  • Year Built: 1976
  • State Abbrv: CA
  • Special Features: None

Interior Features

  • Interior Amenities: Built-Ins, Detached/No Common Walls, Beamed Ceiling(s), Recessed Lighting, High Ceilings (9 Feet+), Living Room Deck Attached, Turnkey, Open Floor Plan
  • Fireplace Rooms: Gas, Fire Pit, Exterior
  • Flooring: Wood
  • Appliances: Built-Ins, Gas, Double Oven, Range, Range Hood
  • Bedrooms: 4
  • Full Bathroom: 4
  • Half Bathroom: 1
  • Bedroom Features: Primary Suite, WalkInCloset
  • Common Walls: Detached/No Common Walls
  • One Quarter Bathrooms: 0
  • Bathroom Features: Powder Room, Shower and Tub, Shower Stall, Double Vanity(s), Double Shower
  • Three Quarter Bathrooms: 0
  • Eating Areas: Breakfast Counter / Bar, Kitchen Island, In Kitchen, Living Room
  • Kitchen Features: Stone Counters, Gourmet Kitchen, Island
  • Laundry: Inside
  • Total Bathrooms: 5.00
  • Equipment: Built-Ins, Freezer, Garbage Disposal, Hood Fan, Dishwasher, Barbeque, Range/Oven, Refrigerator
  • Price Per S Q F T: 1743.08

Exterior Features

  • Other Features: Balcony, High Ceilings (9 Feet+), Sliding Glass Doors, Sprinkler System, Barbecue Private
  • Other Structures: GuestHouse
  • Guest House: Detached
  • Patio: Patio Open, Covered, Living Room Deck Attached
  • Pool Description: In Ground, Private
  • Pool: Yes
  • Spa: Private, Hot Tub, In Ground
  • Spa Yn: Yes
  • View: Panoramic, Ocean, Mountains, Water, Pool
  • View: Yes

Garage/Parking

  • Parking Garage: Driveway, Garage, Parking for Guests, Parking for Guests - Onsite, Parking Space, Unassigned, Uncovered, Private, Gated
  • Total Parking: 6

Utilities

  • Cooling: Air Conditioning
  • Heating: Central
  • Security: 24 Hour, Automatic Gate, Gated
  • Water: District

Condo/Co-op/Association

  • HOA: No

Lot Info

  • Special Zoning: Coastal Commission
  • Sprinklers: Sprinkler System
  • Assessor Parcel Number: 4460-006-012
  • Lot Description: Automatic Gate, Back Yard, Front Yard, Lawn, Landscaped, Fenced, Secluded, Sidewalks, Yard
  • Lot Location: City, Near Public Transit
  • Lot Size Area: 46167

MLS Schools

  • School District: Santa Monica-Malibu Unified School District

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Listed on
Feb 27, 2026
Closed on
May 21, 2026
Sold by
Christopher Cortazzo and Senior Moment Trust
Bought by
Seller's Agent
Chris Cortazzo
Compass
Buyer's Agent
Matthew Schwartz
Plus Real Estate
List Price
$8,250,000
Sold Price
$7,650,000
Premium/Discount to List
-$600,000
-7.27%
Views
127
Current Estimated Value
$7,583,294

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
-$66,706
Avg. Annual Appreciation
-2.79%
Original Mortgage
$3,442,500
Outstanding Balance
$3,433,347
Interest Rate
6.63%
Mortgage Type
New Conventional
Estimated Equity
$4,149,947

Purchase Details

Closed on
Sep 29, 2023
Sold by
Doherty Shannen
Bought by
Senior Moment Trust and Doherty

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$3,000,000
Interest Rate
7.76%
Mortgage Type
New Conventional

Purchase Details

Closed on
Jun 29, 2018
Sold by
Iswarienko Kurt
Bought by
Doherty Shannen

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$2,900,000
Interest Rate
5.62%
Mortgage Type
Adjustable Rate Mortgage/ARM

Purchase Details

Closed on
Jun 20, 2018
Sold by
Kaller Adam
Bought by
Doherty Shannen

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$2,900,000
Interest Rate
5.62%
Mortgage Type
Adjustable Rate Mortgage/ARM

Purchase Details

Closed on
Mar 26, 2014
Sold by
Blatt Steven
Bought by
Kaller Adam and The Senior Moment Trust

Purchase Details

Closed on
Jan 18, 2013
Sold by
Bates Britt M and The Senior Moments Trust
Bought by
Blatt Steven and The Senior Moments Trust

Purchase Details

Closed on
Apr 5, 2004
Sold by
Hayne Robert D and Hayne Deborah W
Bought by
Bates Britt M and Senior Moments Trust

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$1,920,000
Interest Rate
5.25%
Mortgage Type
Purchase Money Mortgage

Purchase Details

Closed on
Apr 24, 2002
Sold by
Walraven Wesley and Walraven Wesley C
Bought by
Hayne Robert D

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$1,623,750
Interest Rate
6.89%

Purchase Details

Closed on
Sep 15, 1999
Sold by
Cappello Mary Ann
Bought by
Cappello Mary Ann

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$1,276,800
Interest Rate
7.25%

Purchase Details

Closed on
Sep 17, 1998
Sold by
Bankers Trust Company Of California Na
Bought by
Cappello Mary Ann

Purchase Details

Closed on
Jul 3, 1998
Sold by
Trust Fireman Barry I Tr Barry I Fireman and Fireman Barry I
Bought by
The Silver Remic Trust I
Source: Public Records

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
$7,650,000 Usa National Title Company
Senior Moment Trust -- Stewart Title Company
Doherty Shannen -- Stewart Title
Doherty Shannen -- Stewart Title
Kaller Adam -- Stewart Title
Kaller Adam -- None Available
Blatt Steven -- None Available
Bates Britt M -- Equity Title
Hayne Robert D $2,165,000 Equity Title Company
Cappello Mary Ann -- Southland Title
Walraven Wesley C $1,596,000 Southland Title
Cappello Mary Ann $885,000 Fidelity National Title Co
The Silver Remic Trust I $735,000 Fidelity National Title
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Open $3,442,500
Closed Senior Moment Trust $3,000,000
Previous Owner Doherty Shannen $2,900,000
Previous Owner Doherty Shannen $2,900,000
Previous Owner Bates Britt M $650,000
Previous Owner Bates Britt M $200,000
Previous Owner Bates Britt M $2,317,000
Previous Owner Bates Britt M $1,920,000
Previous Owner Hayne Robert D $200,000
Previous Owner Hayne Robert D $1,623,750
Previous Owner Walraven Wesley C $120,000
Previous Owner Walraven Wesley C $1,920,000
Previous Owner Walraven Wesley C $500,000
Previous Owner Walraven Wesley C $150,000
Previous Owner Walraven Wesley C $1,276,800
Previous Owner Cappello Mary Ann $975,000
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft
06/05/2026 06/05/26 Sold $7,650,000 -7.3% $1,616 / Sq Ft
05/05/2026 05/05/26 Pending -- -- --
02/27/2026 02/27/26 For Sale $8,250,000 -- $1,743 / Sq Ft
Source: The MLS

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2026 $59,519 $4,891,002 $3,004,002 $1,887,000
2025 $59,519 $4,795,100 $2,945,100 $1,850,000
2024 $41,896 $3,568,413 $1,889,309 $1,679,104
2023 $41,100 $3,498,445 $1,852,264 $1,646,181
2022 $40,572 $3,429,849 $1,815,946 $1,613,903
2021 $39,612 $3,362,598 $1,780,340 $1,582,258
2019 $38,840 $3,262,863 $1,727,535 $1,535,328
2018 $36,833 $3,198,886 $1,693,662 $1,505,224
2016 $35,491 $3,074,671 $1,627,896 $1,446,775
2015 $35,014 $3,028,488 $1,603,444 $1,425,044
2014 $29,959 $2,570,000 $2,240,000 $330,000
Source: Public Records

Agents Affiliated with this Home

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Map

Source: The MLS

MLS Number: 26657743

The MLS

APN: 4460-006-012

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