$8,250,000
27860 Winding WY
Malibu, CA, 90265
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.
Property Details
Price:
$8,250,000
MLS #:
26657743
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
c33malibu
Listed Date:
Feb 27, 2026
Finished Sq Ft:
4,733
Total Sq Ft:
4,733
Lot Size:
46,167 sqft / 1.06 acres (approx)
Year Built:
1976
Schools
School District:
Santa Monica-Malibu Unified
Interior
Appliances
DW, GD, RF, BBQ, BI, DO, RA, HOD
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Flooring
WOOD
Heating
CF
Interior Features
RECL, LRDA, OFP, BC, HCEL
Laundry Features
IN
Levels
U
Exterior
Accessibility Features
NO
Architectural Style
CNT
Common Walls
NCW
Other Structures
GH
Parking Spots
6
Parking Total
6
Patio And Porch Features
CO, OPN
Security Features
_24HR, AG, GC
Spa Features
IG, PVT
View
MT, OC, PA, PL, WA
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Map
Current real estate data for Single Family in Malibu as of Apr 06, 2026
544
Single Family Listed
115
Avg DOM
1,233
Avg $ / SqFt
$5,012,321
Avg List Price
Community
- Address27860 Winding WY Malibu CA
- CityMalibu
- CountyLos Angeles
- Zip Code90265
Similar Listings Nearby
Property Summary
- 27860 Winding WY Malibu CA is a Single Family for sale in Malibu, CA, 90265. It is listed for $8,250,000 and features 4 beds, 5 baths, and has approximately 4,733 square feet of living space, and was originally constructed in 1976. The current price per square foot is $1,743. The average price per square foot for Single Family listings in Malibu is $1,233. The average listing price for Single Family in Malibu is $5,012,321. To schedule a showing of MLS#26657743 at 27860 Winding WY in Malibu, CA, contact your James Outland agent at 8057482262.
Courtesy of Compass. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than James Outland include the name of the listing broker. Neither the listing company nor James Outland shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 27860 Winding WY
Malibu, CA
























































