Bentley Properties

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4415 West Side Road Friday Harbor WA 98250

$ 8,450,000

3 | 1 Full 1 Half | 6483 Sq Feet Send Me Updates On This Property

As evening falls, the residence glows warmly against the forested backdrop, highlighting the refined architecture and expansive glass walls that define this exceptional San Juan Island luxury waterfront estate.

The home’s dramatic architecture unfolds along the shoreline, where floor-to-ceiling glass and natural materials blend seamlessly with the rugged beauty of San Juan Island’s west side waterfront.

At dusk, the residence glows warmly against the landscape, highlighting the nearly 10,000± sq ft architectural design and seamless indoor-outdoor connection overlooking San Juan Island’s pristine west side shoreline.

The property features a striking Bohlin Cywinski Jackson–designed contemporary residence along with a large shop, guest apartment, and gardens, creating a versatile luxury island estate compound ideal for creative pursuits and self-sufficient living.

Bird’s-eye view of the estate’s greenhouse, fenced garden beds, and workshop/garage, thoughtfully designed for those seeking luxury San Juan Island living with sustainability and garden-to-table lifestyle.

A striking example of modern Pacific Northwest architecture, the residence sits just above the shoreline, designed to capture panoramic Haro Strait views and spectacular San Juan Island sunsets.

Golden hour on the west side of San Juan Island, where the home’s long, modern roofline frames breathtaking sunset views over Haro Strait—one of the most sought-after vantage points in the San Juan Islands.

Evening light reveals the home’s dramatic glass walls and refined interiors, capturing the essence of luxury waterfront living on San Juan Island with uninterrupted views of Haro Strait and the Olympic Mountains.

Cooking becomes an experience with panoramic Haro Strait views visible directly from the kitchen, where premium appliances and elegant modern finishes define the space.

The chef’s kitchen features custom cabinetry, expansive stone counters, professional appliances, and skylit wood beam ceilings, blending warm natural materials with refined modern design.

The open great room seamlessly connects kitchen, dining, and living spaces, all oriented toward expansive west-facing water views and breathtaking San Juan Island sunsets.

The sophisticated great room showcases exposed timber beams, custom built-ins, and a sculptural concrete fireplace, creating a warm yet modern gathering space designed to frame the surrounding San Juan Island natural landscape.

The main living area is framed by dramatic floor-to-ceiling glass walls overlooking Haro Strait, allowing the surrounding shoreline and ever-changing water views to become part of the home’s design.

The covered terrace extends the living space outdoors, offering comfortable seating and sweeping views across Haro Strait toward the Olympic Mountains—perfect for year-round outdoor enjoyment.

Wake up to breathtaking waterfront vistas from this serene primary suite, where floor-to-ceiling windows blur the line between indoor comfort and the natural beauty of the San Juan Islands.

A spa-inspired primary bath features dual vanities, a freestanding soaking tub, and a glass-enclosed shower, all positioned to capture serene water views through floor-to-ceiling windows.

Comfortable guest suite with walls of glass opening to tranquil garden and waterfront views, providing a peaceful retreat for visitors.

Another tranquil bedroom retreat framed by sweeping views of the water and surrounding landscape—offering the perfect place to relax after a day exploring the islands.

Modern spa-like bathroom featuring sleek countertops, dual sinks, and an elegant walk-in tile shower designed for both comfort and style.

Spacious lower-level guest suite or flex room offers versatility for guests, recreation, or fitness while maintaining stunning water views through expansive windows.

A beautifully appointed bathroom with custom wood cabinetry, sleek quartz counters, and modern lighting, reflecting the home’s consistent attention to detail and craftsmanship.

Spectacular light-filled workspace with custom cabinetry, multiple workstations, and an entire wall of windows framing breathtaking water views—an inspiring setting for work, creativity, or study.

Inviting media lounge with built-in shelving and modern fireplace creates a cozy retreat for movie nights, reading, or relaxing after a day on the water.

Beautifully appointed bathroom with modern finishes, spacious walk-in shower, and refined design details creating a relaxing spa experience.

Custom wine cellar with extensive wood racking offers impressive storage for a curated collection—ideal for entertaining and wine enthusiasts alike.

The outdoor entertaining terrace features a custom wood-fired pizza oven, perfect for gatherings and alfresco dining while enjoying the serene setting of this luxury waterfront estate on San Juan Island.

Enjoy outdoor dining on the expansive deck where panoramic water views, warm sunset light, and coastal breezes create an unforgettable setting for evenings on San Juan Island’s west side waterfront.

Golden sunset light pours across the property, illuminating the lawn and patio while the horizon stretches across Haro Strait toward the Olympic Mountains—a signature experience of San Juan Island west side living.

Relax along the shoreline where comfortable seating invites quiet moments overlooking Haro Strait, with opportunities to watch passing whales, boats, and unforgettable west side sunsets.

A peaceful seating area set near the shoreline invites quiet moments overlooking San Juan Island’s rugged coastline and expansive open water.

Explore the estate’s natural shoreline and pocket beach, where rocky outcrops, clear water, and native vegetation create a secluded connection to the pristine San Juan Island waterfront.

Entertain or unwind on the expansive waterfront patio featuring a firepit and outdoor dining space, perfectly positioned to take in sweeping views across the water and surrounding islands.

Expansive detached workshop and multi-bay garage provide exceptional space for vehicles, equipment, and creative projects—an ideal complement to this luxury San Juan Island estate.

Expansive professional-grade workshop and garage with vehicle lift, high ceilings, and abundant workspace—ideal for collectors, hobbyists, or creative pursuits within this exceptional San Juan Island estate compound.

A fully equipped greenhouse and productive garden space allow for year-round growing, complementing the estate’s self-sufficient island lifestyle on San Juan Island’s coveted west side.

Thoughtfully designed raised garden beds and greenhouse structures provide a beautiful and functional outdoor space for gardening enthusiasts seeking a luxury island property with sustainability in mind.

A vibrant flower garden surrounded by native forest offers a peaceful retreat, blending curated landscaping with the natural beauty that defines San Juan Island living.

Private west side San Juan Island waterfront estate set on 6± acres with 400± feet of shoreline along Haro Strait. Clearly defined boundaries showcase the rare combination of privacy, forested acreage, and expansive west-facing waterfront.

Striking architectural design meets the natural beauty of the San Juan Islands, with expansive walls of glass and warm wood beams framing panoramic water views from nearly every room.

Spectacular aerial perspective highlighting the estate’s coveted west side location on San Juan Island. Positioned above the shoreline with sweeping views across Haro Strait toward the Olympic Mountains and the surrounding San Juan archipelago.

Listed By: Windermere RE San Juan Islands

Listing ID

#2493364

Property Type

Single Family Residence

County

San Juan

Neighborhood

West

Year Built

2023

Lot Size

Days on website

Description

Set along the coveted west side of San Juan Island, this extraordinary waterfront estate is a striking expression of contemporary architecture by the renowned firm Bohlin Cywinski Jackson. Privately positioned on 6 sunlit acres in 4 tax parcels with 400 feet of pristine shoreline, the residence offers nearly 6,500 square feet of thoughtfully designed living space where modern design meets the island's natural beauty. Dramatic volumes, floor-to-ceilings glass, and warm natural materials create an atmosphere of understated luxury while framing breathtaking views of Haro Strait and the Olympic Mountains. The main level is anchored by a chef's kitchen, sophisticated great room, and a serene primary suite designed for quiet retreat. The lower level offers inviting guest accommodations, a wine cellar, and flexible hobby or studio space. Completing the estate are a substantial workshop and garage, a fully equipped greenhouse, and fenced gardens — ideal for those seeking both beauty and self-sufficiency. Watch whales pass through Haro Strait, enjoy spectacular sunsets, and experience the rare privacy and tranquility that define San Juan Island's most sought-after west side living.

Location

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Financial Information

List Price: $ 8450000

Taxes: $ 50177

Property Features

Appliances: Double Oven, Stove(s)/Range(s), Tankless Water Heater, Trash Compactor

Basement: Daylight, Finished

Exterior Features: Cement/Concrete, Wood Products

Fireplace Features: Gas, Wood Burning

Flooring: Bamboo/Cork, Ceramic Tile, Hardwood

Foundation Details: Poured Concrete

Green Energy Generation: Solar

Interior Or Room Features: Bath Off Primary, Dining Room, Elevator, Fireplace, Pantry, Security System, Skylight(s), Sprinkler System, Vaulted Ceiling(s), Walk-In Closet(s), Water Heater, Wine Cellar, Wine/Beverage Refrigerator

Levels: One

Lot Features: Dirt Road, Drought Resistant Landscape, Secluded

Parking Features: Attached Carport, Attached Garage, Detached Garage, RV Parking

Roof: Metal

Security Features: Partially Fenced, Security System

Sewer: Septic Tank

Structure Type: House

Vegetation: Brush, Fruit Trees, Garden Space, Wooded

View: Ocean, Sound, Strait

Water Source: Individual Well

Waterfront Features: High Bank, Medium Bank, Saltwater, Strait

MLSAreaMajor: 900 - San Juan Island

City: Friday Harbor

Subdivision Name: West

Scan this QR code to see this listing online.
Direct link: https://www.searchproperties.eastsiderealestate.org/listings/direct/194083bbe3311996194fa588220528be

Listed By: Windermere RE San Juan Islands 360-378-3600

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Listings courtesy of Northwest Multiple Listing Service (NWMLS) as distributed by MLS GRID.

IDX information is provided exclusively for consumers' personal non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID.

Based on information submitted to the MLS GRID as of Friday, April 3, 2026 10:09 AM.

All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.

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