A true island sanctuary, this architecturally striking estate spans 47 acres with 440 feet of pristine waterfront, offering commanding views across San Juan Channel to Mt. Baker. Designed renowned firm Hoedemaker Pfeiffer, the 5022 sf main residence is a masterwork of craftsmanship—featuring 3 bedrooms, 3.5 baths, and interiors that gracefully fuse refined comfort with the surrounding natural beauty. A charming 2460 sf guesthouse with 4 bedrooms and 2 baths provides ample space for hosting or extended stays. The grounds are equally compelling with a detached garage, a barn with loft, sport court, and a flourishing orchard. A rare opportunity to own a generational property where design, privacy, and the essence of island living converge.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$8,500,000 (USD)
West Area Residential
Active
4415 West Side Road Friday Harbor, WA 98250
3 Bed
4 Baths
6483 sqft
MLS# 2418238
A rare architectural masterpiece on San Juan Island's coveted west side, this iconic Bohlin Cywinski Jackson-designed estate showcases intentional design and refined craftsmanship across nearly 10,000 sf of conditioned space. Privately sited on 6 acres with 400' of waterfront, the recently completed residence blends soaring spaces, floor-to-ceiling windows, and rich natural materials for a grounded sense of luxury. A chef's kitchen, elegant great room, and serene primary suite anchor the main level, while below offers guests quarters, a wine cellar, and hobby space. The estate includes a workshop/garage, a fully equipped greenhouse, and fenced gardens. Enjoy views of Haro Strait, the Olympics, and visits from whales and wildlife.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$3,700,000 (USD)
San Juan Island Area Residential
Active
148 Yarrow Road Friday Harbor, WA 98250
6 Bed
5 Baths
6276 sqft
MLS# 2380721
A masterpiece of craftsmanship and design, this custom homebuilder's personal residence offers luxury living at its finest. Set on 5 private acres, this 6276 sf Craftsman estate showcases stunning seasonal and waterviews of San Juan Valley, Mt. Baker, San Juan Channel, and Haro Strait. Impeccably maintained, the home features main-level living designed for entertaining, with elegant living, dining, and family rooms, a chef's kitchen, and cozy breakfast nook. Upstairs offers 4 bedrooms, including a view primary suite with a spa-inspired bath. The lower level includes a guest or MIL suite with private entrance, great room, 2 bedrooms, and bath. Enjoy patio surrounded by mature landscaping, 2-car garage, and generator. Relaxing island life!
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$3,645,000 (USD)
West Area Residential
Active
2000 2001 Mount Dallas Road Friday Harbor, WA 98250
3 Bed
4 Baths
4131 sqft
MLS# 2388190
Commanding 360° views from its 22-acre perch atop Mt. Dallas, this extraordinary property spans 2 parcels and captures sweeping vistas from Haro Strait to Mt. Baker. The luxurious, tigerwood-clad main home features a grand living room with stone fireplace, chef’s kitchen with artisan cabinetry and high-end appliances, and 2 elegant water-view suites with spa-like baths. A separate guest suite with kitchen, woodstove, and steam shower offers ideal flexibility. A charming off-grid cabin adds rustic appeal with solar power, wood cook stove, and multi-level decks for dining, stargazing, or tent camping. With water storage, heat pump with AC, high-speed internet, and 2-car garage, this private, versatile retreat is the pinnacle of island living.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$3,470,000 (USD)
San Juan Island Area Residential
Pending
128 Twin Oaks Drive San Juan Island, WA 98250
2 Bed
4 Baths
3176 sqft
MLS# 2344703
Discover an extraordinary equestrian estate on 49+/- dividable acres surrounded by 885+/- acres of National Park land featuring incredible horseback, mountain biking, and walking trails. The property offers breathtaking views of the Straits and the Olympics and includes a beautifully remodeled 3,176 sf, 2 bedroom, 3 bath home with bonus rooms offering natural textures and serene spaces. Enjoy a 2-car garage, tennis court with cabana, tranquil pond, 3-stall horse barn with arena, tack room, granary, multiple pastures, 3,360 sq. ft. barn with shop, RV hook-up, and a charming chicken coop. A true equestrian paradise!
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$2,925,000 (USD)
Orcas Area Residential
Active
8256 Orcas Road Orcas Island, WA 98245
5 Bed
4 Baths
3411 sqft
MLS# 2402006
Refined coastal living in Orcas Village with 345± ft of shoreline and panoramic views across Cayou Channel to Blind Bay! Newly reimagined 3,411± sf , 5BD/4BA residence meticulously remodeled with high-end designer finishes. Featuring mirrored primary suites on both levels, spa-like baths, two bonus rooms, and floor-to-ceiling windows that frame breathtaking views and abundant southwest light. Enjoy two woodburning fireplaces, upgraded HVAC with A/C, and seamless indoor-outdoor living. Launch a kayak from your shore, stroll to the nearby ferry, dock, and village amenities, and return to low-maintenance luxury in a setting that feels like living over the water. An exceptional retreat blending timeless elegance with modern convenience.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$2,750,000 (USD)
West Area Residential
Active
2000 Mount Dallas Road Friday Harbor, WA 98250
3 Bed
4 Baths
4131 sqft
MLS# 2389584
Perched above Haro Strait with panoramic views of Vancouver Island, the Olympics and unforgettable sunsets, this luxurious island retreat blends timeless design with modern comfort. Wrapped in tigerwood decking and siding, the home features a stunning living room with gas fireplace and stone surround, plus a chef's kitchen with high end appliances and artisan cabinetry. 2 elegant waterview primary suites offer spa-like baths with steam showers, soaking tubs, and radiant heat. An office, walk-in pantry, and a separate guest suite with kitchen, woodstove, and steam shower add flexibility and ease. Equipped with a heat pump and AC, water storage, high speed internet, metal roof, 2-car garage, and more. Refined, private, and impeccably crafted!
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$1,950,000 (USD)
San Juan Island Area Land
Active
0 Cattle Point Road Friday Harbor, WA 98250
Bed
0 Baths
sqft
MLS# 2401821
Discover a rare and serene opportunity on San Juan Island - 25+ acres of pristine land featuring three magical ponds, open farmland or pasture ready for your vision, and a thoughtfully selected building site. This unique property offers accessible low-bank waterfront with a gravel beach, gazing out over tranquil Mulno Cove and Griffin Bay. Enjoy peaceful surroundings while remaining just minutes from town amenities. Whether you dream of a private retreat, hobby farm, or legacy estate, this extraordinary setting offers a blank canvas in one of the island's most picturesque locations.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$1,900,000 (USD)
San Juan Island Area Residential
Active
0 East Egg Lake Road Friday Harbor, WA 98250
3 Bed
3 Baths
3306 sqft
MLS# 2407890
New Northwest Contemporary Home - Pre-Sale Opportunity! Be the first to own this beautifully designed, two-level home nestled on 7.46 sunny, pastoral acres. With completion expected by November 2025, this new construction offers 3 bedrooms, 3 bathrooms, and a dedicated office/flex space. Floor-to-ceiling windows flood the grand living room-centered around a striking propane fireplace-with natural light. Engineered hardwood and tile floors provide stylish, low-maintenance living. Enjoy year-round comfort with efficient ductless heat pumps for both heating and cooling. The home also features a durable metal roof, shared well, an oversized septic system, and builder warranty. A modern, move-in ready retreat in the making-reserve your place now
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$1,550,000 (USD)
San Juan Island Area Residential
Active
227 De Haro Lane Friday Harbor, WA 98250
2 Bed
2 Baths
1756 sqft
MLS# 2436342
Peaceful waterfront retreat on Mitchell Bay with no-bank access for clamming, crabbing, or launching your kayak. Picture windows frame enchanting bay views, while a wood-burning stove adds cozy charm. The home offers both a living room and family room, plus a dining area with easy flow to the deck and patio. The primary suite features French doors opening to a private deck and an updated en-suite bath with oversized shower. Additional updates include new flooring and refreshed main bath. Relax in the new hot tub after a day of hiking, biking, or kayaking. Nestled in a quiet neighborhood, yet minutes to Roche Harbor Resort, marina, spa, Mount Young trails, and British camp National Park.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$995,000 (USD)
Roche Harbor Area Residential
Active
295 Westcott Drive Friday Harbor, WA 98250
3 Bed
2 Baths
1690 sqft
MLS# 2408956
Built in 2023 with modern convenience in mind, this Westcott Bay home offers low maintenance living just minutes from Roche Harbor’s dining, marina, and shops. Vaulted ceilings and a gas fireplace set a welcoming tone, while durable luxury vinyl plank floors and quartz countertops combine style with easy care. The open kitchen is ideal for everyday use and entertaining, and the spacious primary suite is a private retreat. Thoughtful features include ductless heat pumps for year-round comfort, plus solar and generator readiness for peace of mind. Enjoy the back deck, a sunny backyard, and private community beach access—along with a short stroll to the local oyster farm. A perfect blend of new construction, efficiency, and island convenience.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$995,000 (USD)
San Juan Island Area Residential
Active
437 Woodpecker Lane Friday Harbor, WA 98250
3 Bed
2 Baths
1771 sqft
MLS# 2426497
Experience San Juan Island living in this well-maintained 3 bed, 2 bath rambler on 2 acres with pond and Sportsman's Lake access. This 1771 sf home features an open floor plan, gas fireplace, stainless appliances, and natural stone countertops throughout. Spacious primary suite includes a WIC and 5-piece bath with soaking tub and oversized shower. Enjoy the 3-car garage, raised garden beds, fruit trees, and back deck overlooking the lake with abundant wildlife. Sportsman's Lake Park amenities include a community waterfront and dock. Centrally located between Friday Harbor and Roche Harbor, with a compliant vacation rental permit in place - this move-in-ready home is an ideal year-round residence or income-producing retreat.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$895,000 (USD)
West Area Land
Active
2001 Mount Dallas Road Friday Harbor, WA 98250
Bed
0 Baths
sqft
MLS# 2389070
Perched atop Mt. Dallas on 17 acres of natural splendor, this off-grid retreat captures breathtaking views of San Juan Channel, Mt. Baker, and the vibrant valleys below - where each season paints a new masterpiece. Gaze out to glimpses of Haro Strait from your own multi-level tigerwood deck, perfect for dining, gathering around the firepit, or pitching a tent under the stars. The charming, solar-powered cabin offers warm hardwood floors, a wood cook stove, propane refrigerator, copper-accented sink, and a composting toilet - simple luxury in harmony with nature. With two access driveways and a completed soil test, this property invites you to enjoy weekends away or envision your future dream home in the sky.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$499,000 (USD)
Town Area Townhouse
Active
1032 4 Guard Street Friday Harbor, WA 98250
2 Bed
2 Baths
1017 sqft
MLS# 2436697
Presale Opportunity End Unit! ***Special, Limited time 3.99% financing OAC*** The Grove townhome community in the heart of Friday Harbor, blending modern design with San Juan Island's natural beauty. These 2-bed, 2-bath homes offer high-end finishes, functional layouts, and indoor-outdoor living. With flexible financing and low interest rate options, homeownership is within reach. Whether you're seeking a full-time home or a weekend escape, The Grove offers island serenity and everyday convenience in one of the Pacific Northwest's most stunning locations.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$499,000 (USD)
Town Area Townhouse
Pending
1032 16 Guard Street Friday Harbor, WA 98250
2 Bed
2 Baths
1017 sqft
MLS# 2411126
Presale Opportunity! The Grove townhome community in the heart of Friday Harbor, blending modern design with San Juan Island's natural beauty. These 2-bed, 2-bath homes offer high-end finishes, functional layouts, and indoor-outdoor living. With streamlined modular design, flexible financing and low interest rate options including ***4.99% OAC with Preferred Lender***, homeownership is within reach. Whether you're seeking a full-time home or a weekend escape, The Grove offers island serenity and everyday convenience in one of the Pacific Northwest's most stunning locations.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$479,000 (USD)
Town Area Townhouse
Pending
1032 2 Guard Street Friday Harbor, WA 98250
2 Bed
2 Baths
1017 sqft
MLS# 2444505
Presale Opportunity Interior Unit! The Grove townhome community in the heart of Friday Harbor, blending modern design with San Juan Island's natural beauty. These 2-bed, 2-bath homes offer high-end finishes, functional layouts, and indoor-outdoor living. With flexible financing and low interest rate options, homeownership is within reach. Whether you're seeking a full-time home or a weekend escape, The Grove offers island serenity and everyday convenience in one of the Pacific Northwest's most stunning locations.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$299,000 (USD)
Blakely Island Area Land
Pending
155 Driftwood Drive Blakely Island, WA 98222
Bed
0 Baths
sqft
MLS# 2257697
Breathtaking land opportunity on Blakely Island! Discover the perfect island escape with this stunning ½+ acre lot, offering captivating views of Mt. Baker and Peavine Pass. Enjoy the serene beauty of the San Juan Islands with easy access via a paved road and a short walk to 1,000+ feet of low-bank community waterfront. This prime location is just moments from sought-after community amenities, including a private airstrip, peaceful ponds, a marina, and a seasonal store. Whether you arrive by boat or plane, getting here is effortless. Embrace the tranquility of island living and build your dream retreat in this unparalleled setting!
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King
$235,000 (USD)
Town Area Land
Active
365 Marguerite Place S Friday Harbor, WA 98250
Bed
0 Baths
sqft
MLS# 2361397
Prime In-Town Opportunity – Multifamily Lot with Utilities Installed! Unlock the potential of this versatile .26-acre lot in the heart of Friday Harbor on San Juan Island. Zoned multifamily, this property supports up to 4 units (buyer to verify), making it ideal for income-producing development or a personal build project. Water, sewer, and electricity are already in place—saving time and money on infrastructure. Enjoy potential second-story water views and walkable access to shops, restaurants, and the ferry. Whether you're an investor, developer, or hands-on builder, this is a rare find in a sought-after location.
Listing Courtesy of Northwest MLS / Windermere Real Estate San Juan Island / Greg King